How to Get to 10M in ARR and Beyond Dilek Foreword

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Copyright © 2019. Published by Winning By Design, LLC, a Delaware Company 
All rights reserved as permitted under the United States Copyright Act of 
1976. No part of this book may be reproduced, used or distributed in any form 
or by any means, without expressed written consent of the publisher. The 
contents of this book were created in the United States of America. 
 
 
Revision 2.0 
 
 
Winning By Design LLC 
3000 Sand Hill Road, Building 4, Suite 210 
Menlo Park, CA 94025   
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WHY YOU SHOULD READ THIS BOOK 
This book was written for anyone who works with customers. It is based on a scientific understanding of 
how revenue generation works in a recurring revenue business. That revenue generation model poses the 
same questions for the CEO as well as for those in sales, marketing, and customer success: How do I 
grow the business? How do I get my team to perform? Should I hire more people? Why are my customers 
churning? Should I run more campaigns? Should I buy more leads? This book will give you the answers to 
these questions and many more.   
This book contains insights gained from working with over 300 companies over the span of four years. 
Many of them are early-stage, high-tech startups but the list also contains some of the largest companies 
in the world. The insights we found are the same across all of them:   
1. A maniacal focus on new logo acquisition versus generating profits from existing customers. 
2. The first response when targets are missed is to blame the people, not to inspect the process. 
3. Absence of a uniform methodology across all roles dedicated to the recurring business model.  
4. Little understanding of the unit economics that make a recurring business work. 
5. Inadequate depth of basic sales skills; everyone is looking for tricks/hacks and shortcuts.  
We provide simple answers to address all of the issues. With the knowledge in this book, we aim to enable 
you to have a strategic conversation in the boardroom, a one-on-one talk with a 30-year sales veteran on 
the changes in selling, discuss a new LeadGen initiative with the marketing manager, or coach a customer 
success manager on how to upsell a customer. It’s all here. This book was written so the chapters can be 
read in any order. Page through it and if you see a visual you like, dive in; that’s your starting point. 
 
 
 
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TABLE OF CONTENTS 
 
 
FOREWORD BY DYLEK   
CHAPTER 1 INTRODUCTION 10 
CHAPTER 2 ORGANIZATION 24 
CHAPTER 3 THE SALES PROCESS 46 
CHAPTER 4 TECHNOLOGY STACK 60 
CHAPTER 5 PROFESSIONAL SKILLS 76 
CHAPTER 6 SALES ENABLEMENT 92 
CHAPTER 7 THE SAAS METHODOLOGY 104 
CHAPTER 8 DATA-DRIVEN ORGANIZATION 128 
CHAPTER 9 CULTURE 142 
   
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ABBREVIATIONS USED 
ACV Annual Contract Value 
AE Account Executive 
AM Account Manager 
ARR Annual Revenue 
B2B Business to Business 
B2C Business to Consumer 
BDR Business Development Representative 
CAC Client Acquisition Cost 
CR Conversion Ratio 
CRM Customer Relationship Management 
CSM Customer Success Manager 
CE Critical Event 
CEO Chief Executive Officer 
CRO Chief Revenue Officer 
CCO Chief Customer Officer 
DEMO Demonstration 
ICE Impact and Critical Event 
 
LTV Lifetime Value of a customer 
MAS Marketing Automation System 
MDR Marketing Development Representative 
MQL Marketing Qualified Lead 
MRR Monthly Recurring Revenue 
MTM Moment That Matters 
ORG Organization 
POC Proof of Concept 
ROI Return on Investment 
SaaS Software as a Service 
SAL Sales Accepted Lead 
SDR Sales Development Representative 
SMB Small to Medium Business 
SQL Sales Qualified Lead, same as Opportunity 
VSB Very Small Business (emerging) segment 
WR Win ratio 
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FOREWORD 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
7 
 
I’m delighted to offer a short introduction to Winning by Design’s latest book, “How to get to $10m                                   
ARR and beyond.” 
 
We believe that our active partnership with our entrepreneurs is far beyond mere capital injection. 
Instead, we thrive on being a valuable strategic partner, bringing our exceptional operational and 
entrepreneurial experience. We are here to create the conditions for the extraordinary success for 
founders who share our burning desire to build global, category-leading technology companies. 
 
To support entrepreneurial scene in the region, we are annually bringing the ScaleX Founders Summit 
with the most talented tech founders, CEOs and senior executives for a day of intensive learning. On 
this day, we try to touch every fragment of startup operations, from sales to talent. While we were 
looking for the best experts who could help selected founders and CEOs, we got stuck at finding the 
right person who could help the entrepreneurs to build a successful sales strategy. At that point, I’ve 
reached out to my top VC and CEO friends from all around the world. After Jacco’s name popped up on 
my phone many times, I decided to contact him. Funny thing is, he was on vacation and I needed to 
chase him for a while. After our first call, and couple of reference calls I was so impressed. ​However, I    
was wondering how much of what he said about SaaS sales strategies and models would really play                                 
out in domain expertise, insight, and most importantly in practice. Achieving predictable, repeatable                         
and scalable revenue is the goal for any SaaS company, especially when venture-backed. We had                             
long been looking for an individual or team to lead a best practice charge on this topic for our                                     
portfolio, someone we could consider “the best on the planet”. I knew a little about Jacco, and less                                   
about Winning by Design, but I had a feeling he might be the one. 
  
It quickly became apparent since one of our close advisors, Berkay, had built the sales strategy with                                 
Jacco’s methodology. ​Berkay, CEO of Opsgenie which has 3000+ customers all over the world and    
made one of the biggest startup exits in Europe in 2018, I decided to call him immediately. After hearing 
what he said, I was sure that he was the speaker I was looking for. 
 
“When I was designing sales structure for Opsgenie, I somehow found Jacco’s “The SaaS Sales 
Method: Sales As a Science”. It guided me through the basics of SaaS sales and helped me learn the 
different approaches of selling our unique software.” 
- Berkay Mollamustafaoglu, CEO, Opsgenie. March 2019 
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Also, one of the most well-known venture capitalists, Itxaso from Notion Capital and a Kauffman Fellow, 
spoke very highly of Winning by Design and Jacco. 
 
“​If you are looking for an individua​l or team to show you the best practice on ​sales and other            
go-to-market issues​, here is your man​. He helped many of our portfolio companies on their sales                      
development and growth.​” 
- Itxaso del Palacio, Investment Director, Notion Capital. April 2019 
 
​Ultimately, I am very proud to announce that we’re hosting Jacco at Istanbul for our annual summit. 
Alongside, I would like to offer you this great outline of how to approach sales and the changing world. I 
believe that this book is an excellent and practical short read that guides entrepreneurs and sales 
leaders in setting up their sales process. 
 
As it’s said “ Sales is always the best solution to the problems in a start-up”. 
 
In this book, you will find out which moments matter, from the perspectiveof the customer, and how 
you can build a sales process that delivers these moments. Also, you will see how the underlying 
patterns of the sales process has changed and the new selling models that have emerged as a result. I 
believe Jacco can be confident that there will be many grateful readers who will gain a broader 
perspective on the SaaS sales process, thanks to this exclusive guide. 
 
Dilek Dayınlarlı, Managing Partner, ScaleX Ventures. 
  
At ScaleX Ventures, we focus on early stage investments. We believe in the power of technologies that                                 
can make the world a better place.We invest in founders with a vision to achieve this on a massive                                     
global scale. As a team of company builders, we have walked through this path many times, we know                                   
what it takes, both physically and mentally, and are eager to provide the hands-on support you need to                                   
help accelerate your journey. 
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CHAPTER 1  
INTRODUCTION 
 
 
   
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This document contains the best practices and industry knowledge that Winning by Design has gained 
from working with hundreds of startups over the past several years. It contains easy-to-understand 
guidance and actions that, as founders and executives, you can put into practice right away. 
THREE KEY PHASES OF SCALING A BUSINESS 
 ​ Table 1.1​ Key phases of scaling a business 
START UP | <$1M ARR  GROW UP | $1M - $3M  SCALE UP | $3M - $10M ARR 
The company is finding product         
market fit with 10-20+ customers         
and up to $2M in ARR in its               
original market/region. The     
founder(s) is still closing most         
deals, leading sales and       
marketing, has recently closed a         
seed round, and is working         
toward an A round.  
 
The company is ready for its first             
sales hire to start driving deals           
right away, to expand 2-3x in the             
next 12 months. This means         
moving from more anecdotal       
founder sales to building a         
professional sales team.  
The company has grown to $2M           
in ARR, and needs to bring in             
some best practices to scale         
sales efforts and start thinking         
about customer success to       
continue its growth. It has closed           
or is in the process of pitching a               
Series A of funding.  
 
The company must scale rapidly         
across different vertical markets. It         
is hiring its first one or two sales               
reps, and potentially looking to         
hire a VP of Sales to institute             
formalized process, systems and       
strategy for better productivity       
and predictability in pipeline. 
The company is now better         
established with revenues of at         
least $5M ARR (50+ customers)         
and with a view to be at $10M               
within two to three years. The           
company should be looking to hire           
specialized roles on the sales         
team, perhaps two SDRs and three           
to four AEs.  
 
Also needed are detailed       
processes and metrics, and       
implementation of best practices       
into commercial teams to maintain         
competitive advantage and focus       
on customer retention and       
expansion. It also may need to           
address new markets and open         
new regions to expand sales. 
 
   
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INFRASTRUCTURE AND BUILDING BLOCKS FOR SCALING YOUR GROWTH 
 
When you scale a company for growth, you metaphorically want to avoid building a 20-story building on 
top of a foundation that was originally meant for just two stories. You must build a company with scale 
design principles in mind. Below is an overview of these basic design principles that will enable you to 
scale, compare, and leverage best practices from your fellow portfolio companies. 
 
Table 1.2​ Key elements of a Go To Market sales organization 
INFRASTRUCTURE 
Culture  A customer-centric culture: not hard-driving selling, but rather assisting 
customers through the buying process by educating them along the way 
Methodology  The key moments that matter along a customer’s journey, and how you 
should apply customer-centric principles to maximize your impact  
Data Model  A baseline data model that will provide structure for your metrics, simplify your 
CRM implementation, and give you a framework to compare metrics with 
your peer companies 
KEY BUILDING BLOCKS 
Process  Proven simple processes that can be implemented the right away and iterated 
over time as your business grows 
Technology  A tool stack that acts as a force multiplier and grows with you as you scale  
Enablement  Training and materials provided to your customer-facing sales roles with the 
latest knowledge and skills to help educate the prospect 
Skills  The skills required for each specialized role on your sales team for excellence 
throughout the sales cycle 
Organization  A scalable organization that works as a team, designed to scale and prepared 
for success 
 
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Figure 1.1​ The Elements of a Scalable Design 
 
UNDERSTANDING GROWTH  
Historically, growth of a sales team was based on annual revenue, and the rate of growth was fairly 
dependent on the size of the sales team; doubling revenue would probably require hiring twice as many 
people. However, in a SaaS model, it’s entirely possible for a sales team to double revenue without 
doubling the team through growth in new customers as well as renewal and expansion of existing 
customers. Many leaders have not yet grasped this model of growth, and it leads to many 
misunderstandings as founders are trying to grow their companies. 
 
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Figure 1.2​ Difference between traditional sales growth and SaaS sales growth 
 
As you can see above, the rate of growth slows down if you grow by the same amount of revenue each 
year. So in order to keep the growth rate steady or increasing, it requires a significant investment in the 
acquisition efforts, as depicted in Figure 1.3.   
 
Figure 1.3​ SaaS Growth Rate 
   
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GROWTH POTENTIAL 
In the B2B SaaS space, there are a lot of new factors bringing exponential growth to SaaS companies:  
#1 An increase in online spend: ​Startups, regional 
businesses and global corporations alike are becoming 
more comfortable spending budget on SaaS services. 
Spending $1K on one service was once thought 
extreme, but today buyers are becoming comfortable 
spending $5K-100K or more. 
  
#2 A bigger marketplace: ​Every seller now operates 
in a much bigger marketplace with technology giving 
them easy access to buyers in all markets and regions. 
There is an always-growing set of tools and software 
that allow companies to sell from anywhere, 
circumventing the traditional field sales limitations. 
  Figure 1.4​ Where growth expectations originate 
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WHEN TO ACCELERATE? 
The term “growth hacking” is being tossed around 
quite a bit these days. Growth hacking is essentially the 
idea of figuring out a process of shortcuts to bring 
more growth, faster. One of these popular shortcuts is 
to use automated methods of outreach to possible 
customers to book meetings, and then use low-cost 
sales resources to run those meetings in an effort to 
close. Initially this worked well, particularly post-2008 
when SaaS solutions were becoming popular because 
of their classification as Operating Expense (rather than 
conventional CapEx solutions). But today, everyone 
offers a SaaS/OpEx solution, and these methods of 
growth hacking no longer produce the desired results.  Figure 1.5​ Early stages of growth  
 
Table 1.3​ Keys to scaling a business and minimizing the risk of failure   
Key #1  
Find Product-Market Fit  
Key #2  
Hit the Launch Window 
Key #3  
Execute the GTM Plan 
Product-Market Fit is whena 
mature product can satisfy a 
market, and where there there is 
plenty of growth potential. It’s 
quite difficult to achieve 
product-market fit in a market 
where innovative solutions are 
launching regularly and the 
markets are never constant. 
A common mistake that startups 
make is achieving their 
product-market fit but waiting too 
long to scale to meet the market 
potential, thus missing the ideal 
launch window. These companies will 
become, say, #4 or #5 of the list of 
recommended solutions with a small 
sliver of market share. Today, the 
launch window has shrunk from 
18-36 months down to 9-18 months 
after finding product-market fit. 
The third and final hurdle to hit rapid 
growth is to execute the right Go To 
Market plan often attributed to 
growing sales. It is the least 
understood topic of these hurdles. 
Success in executing the GTM is 
not measured in growth rate [%] or 
revenue [ARR], but rather against 
the growth potential within the 
market. 
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KEY #1. FIND PRODUCT-MARKET FIT 
 
One of the keys to growth in today’s 
SaaS business model is to identify 
your product-market fit using a 
variety of sales and marketing 
channels (or GTM strategies). 
 
But here is where many organizations 
slip up: they are often looking at the 
overall result rather than using 
metrics to measure effectiveness and 
efficiency of each GTM strategy. You 
might have a great product, but if 
you don’t figure out how to reach the 
market through an optimal GTM 
strategy, you won’t reach your users 
in the market.  
 
 
Figure 1.6​ Results of the lack of a GTM fit 
These are the keys to growth that you should identify while you are exploring Product-Market Fit: 
● What is the value proposition that prioritizes the solution offered? 
● Who is the audience that has a real problem and is willing to take action?  
● How do we reach the audience with the real problem in an efficient and effective way? 
 
Without measuring effectiveness in reaching the market, you can kick off an unfortunate downward spiral. 
With no measurement, growth may slow or stagnate, the company might achieve a lower valuation than 
their potential, sales leadership might turnover, and new leaders will be left trying to figure out if the issue is 
due to poor product-market fit or poor sales team performance.  
   
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KEY #2. HIT THE LAUNCH WINDOW 
 
How do you know when you are in the launch window? There are three clear, telltale signs: 
 
● Price increases:​ Instead of closing deals at $10K, you start closing deals at $15-20K ARR. This 
indicates that you are offering real value and your customers are starting to understand the impact 
of the value on their organization. 
 
● Win rate increases: ​Win rate is measured by the number of Sales Qualified Leads (or SQLs; find 
out more about metrics like this in later chapters) needed to win one deal. Instead of winning one 
out of six deals, you now win one out of five deals. This is indicative of a stronger position in the 
market. 
 
● Sales cycle decreases:​ The sales cycle is measured as the time between an SQL being created 
and until a deal is won. For example, your average sales cycle is now 71 days instead of 84 days. 
This indicates that your customers are prioritizing your solution and having an easier time making a 
purchase decision. 
 
Figure 1.7​ How to determine when you are in a launch window 
 
What do these telltale signs have in common? They are data driven: They are factors you can measure, 
and when interpreted correctly, can be used to make a data-driven decision.    
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Don’t fall for these common mistakes, which will incorrectly lead you to believe you’re in the launch window:  
● Too few deals - Your data will be skewed by a small sample size 
● Not distinguishing outliers - Identifying outlier deals that are skewing your results 
● Poor data entry - For instance, if you record some deals only after they close, it will skew your sales cycle to 
be shorter than it actually is. 
 
KEY #3. EXECUTE THE GTM PLAN 
 
To achieve your maximum growth potential, you need a solid Go To Market (GTM) plan. Companies will 
often secure a new round of funding to execute their new GTM: Paying for the recruitment of sales people, 
increasing expenditure on marketing campaigns, attending events, and building your first custom booth at 
a conference. Most organizations will use the world's most common scaling plan: Do 3x of what you were 
doing that got you to this point. As you can see in the figure below, even when we grow the sales team by 
3x, scaling to meet your potential can remain a challenge. 
  
Figure 1.8 ​ A funding round to scale growth may not result in the desired growth rate 
 
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This is often experienced by companies that depend primarily on an “outbound” approach - reaching out 
to customers proactively rather than interested leads coming to them first. These companies find out the 
hard way that tripling the sales team and tripling the activities does not always triple the result. Instead, you 
need a modern GTM model. Start thinking of your revenue as being composed of layers. For example: 
 
● Regionalize teams​ to increase coverage and decrease dependency on your local market 
● Add new products/services ​to uplift the price and create upsell/cross-sell opportunities 
● Pursue new accounts ​such as moving from small business to midmarket, or pursuing new 
verticals 
● Add a strategic partnership ​that opens up an entirely new segment 
 
Going after bigger deals is not just taking your best salespeople and giving them a list of larger target 
buyers. Rather, you need to segment the market and develop a new GTM plan for that market. Recognize 
that the needs for startups or smaller businesses may be different from a midmarket or enterprise 
company. 
 
Figure 1.9​ Layering of revenue: each layer may need a different GTM strategy 
 
 
   
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Table 1.4​ Who is responsible for each of these areas as the company scales? 
INFRASTRUCTURE  START UP  GROW UP  SCALE UP 
Culture  Founder  Founder  CEO 
Methodology  Founder  VP/Dir. Sales  CRO/VP 
Data   Founder  VP Finance/Dir. Sales  Data Analyst 
 
BUILDING BLOCKS  START UP  GROW UP  SCALE UP 
Organization  Founder  Founder/VP/Dir. Sales  VP Sales+VP HR 
Enablement  Founder  Dir. Sales + VP Marketing  Sales Enablement 
Skills  Founder  VP/Dir. Sales  VP Sales 
Technology  Founder  VP/Dir. Sales  Sales Operations 
Process  Founder  VP/Dir. Sales  VP/Sales Ops 
   
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CHAPTER 2 
ORGANIZATION 
 
   
24 
 
This chapter will show you how to build your sales team in a scalable way through a phased approach. 
 
Phase 1: Start Up 
In the Start Up phase, the founders are building the company and selling at the same time, likely along with 
some others in the company who are also pulling double duty. If you have one founder, they are often 
splitting time between building the product and trying to close the first few deals. If you have a co-founder, 
or second most senior person, they are likely focusing on the engineering and delivery of the product. This 
is also referred to as the ‘Mom-n-Pop’ model - with one focusing on winning customers, and the other on 
delivering said product. 
 
 
Figure 2.1 
Co-founders (F1 
and F2) are working 
the entire sales 
cycle themselves, 
commonly known 
as Founder Sales 
Mode. 
To explain the chart above (this chart will appear a few times throughout this book to visualize how your 
sales team should evolve in each phase), here are the different milestones of the sales cycle:  
 
PROSPECT  A person who expresses interest by visiting a website or other piece of content 
MQL  Marketing Qualified Lead, a person who expresses interest in your product ​and​ fits the target profile 
SQL Sales Qualified Lead, a person who experiences a pain that you are addressing with your product and                                 
wants to take action  
COMMITMutual commitment to deploy a solution that will achieve impact at a set time 
LIVE Customer has been onboarded: on time, within budget and the solution can deliver impact 
MRR The solution delivers impact again and again, and a recurring revenue stream is secured 
LTV The revenue an account generates over the lifetime, net of churn and including growth  
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In Figure 2.1, one founder (“F1”) focuses on the pre-sales motion, while the second founder (“F2”) focuses 
on customer success after the purchase has been made. As you can see, it’s a lot of ground to cover for 
founders.  
 
Q: Should I hire a sales person right away? 
A: No. You should close the first deals yourself. ​This allows you to learn what your customers 
value the most in your offering. It also sets you up for longer term success. In later phases, you will 
have a sales team running their own deals, but for the most strategic deals, you will be pulled in to 
assist and likely meet with buyers such as CEOs and strategic decision makers. So, understanding 
first-hand what goes into closing a deal will help you be more effective later on. 
 
 
 
EXPERT ADVICE ​As the founder, you are your company’s first salesperson. Before you 
determine who to hire, you first have to do it yourself to learn what customers respond to 
and why. 
DEREK SATHER 
Sales Architect, Winning by Design 
 
 
Q: How many deals should I close as a founder? 
A: Around 20-25. ​Not less than 10, as these first few customers will likely be from innovators, and in 
some cases, customers with whom you already have built a rapport. As such, they will probably not 
provide you with real insights if the value proposition works. But don’t sell significantly more than 25 deals 
yourself. You will begin to neglect your obligation to lead a growing company if you are too busy focused 
on individual deals. 
 
Q: We are a product company. Can’t I just outsource sales to a channel partner that already has 
a network? 
A: No.​ At an early stage, it is crucial that you and your team are owning the relationships with your 
customers as well as learning from the selling process to understand what is resonating in your market. If 
outsourced, that crucial knowledge would be difficult, if not impossible, to access through a third party. 
26 
 
Further, partners simply are not going to be able to represent your product, answer detailed questions, 
and give insights to your customers in the way that ​you​ can as a founder. 
 
Phase 2: Grow Up 
So you’ve now closed your first 10-20 deals and you’ve reached approximately $2M in ARR. You have 
some momentum. As a founder, it feels like you are working at breakneck speed to generate leads - doing 
a lot of the outbound work, speaking at local meetups and even speaking at trade shows generating some 
inbound interest.  
 
You may feel like leads are not followed up on properly, and maybe like things are falling on the floor. It’s 
time to hire the first salesperson to sustain and grow from the initial sales momentum you are creating. 
 
 
Figure 2.2​ The founder 
is doing outbound 
activities, but an AE is 
added to manage 
inbound, and then later 
to handle lead follow-up 
as well. The AE will 
need training and 
coaching by the founder 
in order to effectively 
sell as the founder has 
done. 
The role of your first Salesperson  
In this phase, you are making your first sales hire. As the first hire, they must be able to work across the 
entire ​sales process, prioritizing and handling inbound leads, and then driving them to close (while the 
founder continues working the outbound leads that he has generated). This ability for the first rep to work 
across the entire sales cycle is unique! Generally, they should have at least four to six years of experience 
working in your industry (and remember, sometimes this person could be one of your customers - such as 
a former educator or dean of admissions). More specifically, here is what that person should be able to do:  
● Prospect for leads as well as close deals 
27 
 
● Understand the value of your product, and genuinely articulate the value 
● Be enthusiastic about the mission of the company and what it stands for 
● Be ready for change! Things change quickly and often at this stage (product, pricing, etc.), so this 
person must be able to roll with the punches 
● While he or she may not be building the product alongside you, they should be very familiar with 
the strategy and where the product is going 
● Passionate about the industry and know how to navigate it and speak the market lingo  
● Easy to communicate with; you will both need to rely on each other quite a bit.  
● Fun to have around! After all, this person is going to help set the tone for subsequent sales hires. 
And as we will learn in subsequent chapters, culture is key.  
 
These are things you should NOT consider to be critical characteristics for a sales hire at this stage:  
● “Cuff link VP”: With several years of experience selling, you can hear the cuff links hit the table 
during the interview (so to speak). This person will likely not want to do (or be good at) the 
practical, hands-on work that is needed during this first phase. 
● Enthusiastic go-getter: This is likely a person early in their career with an entrepreneurial spirit and 
high energy. Enthusiasm is great but it can’t substitute for experience if they haven’t had sales 
roles before. Having experience is critical to informing a strong sales org foundation. 
 
Commons Questions 
Q. I know a great sales rep from the past - they can sell really well, but they aren’t familiar with 
my product or market. Should I hire them?  
A. No.​ It is critical for the first hire(s) that they know the market and are passionate about what you are 
trying to do. They are mission - NOT commission - driven. In the startup phase, you need people on the 
team who can sell by evangelizing, educating and connecting your product with the right people in the 
market. This depth of market understanding is critical at this phase. Having strong negotiation skills and a 
track record of exceeding quotas does not guarantee success. 
 
Q. How do I know if I made a good hire? 
A. ​If the rep hits his quota but cannot implement a solid sales process, this will not lead to sustainable 
growth. If he hits quota AND can establish process, then things are looking good. If he can do all of that, 
AND can coach others on the team, then you’ve found yourself a great hire. Or shown another way:  
28 
 
Table 2.1​ Framework for identifying a strong early hire 
  HITS QUOTA?  ESTABLISHES 
PROCESS? 
COACHES OTHERS? 
Below-average 
first sales hire 
Every now and then  Not much  Not happening 
Good  
first sales hire 
Usually, but will let you 
know in advance if they will 
miss it 
Sometimes gripes about 
having to follow process  Coaches others when asked 
Great  
first sales hire 
Most of the time  Establishes and improves 
on sales processes 
Proactively coaches 
teammates  
 
Q. How long should I wait for my new sales reps to hit their quotas? 
A. ​This depends if your product is an application or a platform. What we’ve seen by working with dozens 
of customers is that for application-based sales, it should be 60 days for new sales reps to hit quotas. For 
platform sales, it could be as long as six months.  
 
Q. ​Some people have suggested that it’s best to hire two sales people at once so that you can 
compare them and give them someone to work with - what are the pros and cons?  
A. Well, yes and no… 
 
If you’re hiring two sales reps (Account Executives) for the same territories at once, then no. 
This tactic is an industry fairytale that usually backfires. Here’s why: At this stage, you should not be 
double-hiring positions; you should be hiring the right people. Now if you want to hire two sales people 
instead of one and put them in two different territories, that works. The idea of “letting them fight it out” 
does not take intoaccount that modern sales professionals should not be competing with each other, 
but instead working as a team.  
 
If you’re hiring an SDR/AE (Sales Development Rep/Account Executive) to grow together as 
a team, then yes. ​Hiring this way to start up your sales team can help establish a good process from 
the start, and finding two personalities who work well together can be very beneficial. 
 
29 
 
Q. ​How do I compensate this new sales person?  
A. Great question. ​Refer to Chapter 9 for all about compensation.  
 
Q: What if the first sales rep wants to work remotely? 
A: No. ​These first hires need to learn from the founders, and that means being in the room. You’re 
swamped, constantly running from events to VC meetings to customer meetings, and you need to be able 
to share learnings with them face-to-face for the short time that you’re actually at your desk. It’s critical 
that they are able to pick up knowledge while they sit next to you, to ask you questions in real time, and to 
absorb the language of the company. 
 
Q: What if they want to work part time? 
A: Potentially. ​It’s better to have a superstar person part-time rather than a so-so performer full-time (for 
more on what a ‘superstar’ looks like, see Chapter 9). However, not just any part-timer will fit your needs 
here. Most often, the successful part-timers are parents who are returning to the workplace, or people 
who are returning after some kind of (productive) hiatus from full-time work. Either way, they are more 
senior rather than junior in sales. If you’re hiring part time, then the profile must be someone who already 
has work experience - not a first job for someone out of college.  
 
If you decide to allow part-timers, then be sure that they come into your office when they do work (not 
working remote), are working at least 25 hours per week, and are working those hours that line up with 
your business. Here’s an example: If part-time means they can only work mornings, whereas your decision 
makers are only available in the afternoons, then that is a problem. But with the example of returning 
parents, their desired work schedule and motivations sometimes are similar to those of your existing 
executives - working specific hours during the day, picking up kids after school, perhaps logging back 
online in the evenings after kids are in bed. 
 
We’ve seen part-time sales hires work quite well under these conditions . . . however, this can be really 
tough to manage successfully, so consider this only for the candidates that you just can’t bear to lose, and 
proceed with caution.  
 
Q: What should I prioritize? The number of total customers or total revenue?  
A. This will be a function of your product.​ If you are selling a platform, you are aiming for number of 
logos, as the relationship between logo and revenue is linear (assuming you have a fixed price) - and 
30 
 
included in this is acquiring customers that you can reference externally. If you are selling usage, or any 
other element that can increase over time, then you should prioritize for revenue growth.  
 
Common Pitfalls 
 
Pitfall 1: Not creating a formal price list. ​You may feel that the salesperson won’t be able to close 
deals at the same price that you can without the deep product knowledge that you possess. To avoid this 
confusion, you should formalize a price list and agree to a discount give-take list.  
Pitfall 2: Allowing discounting free-for-all. ​Perhaps you have a firmly published price, but a variety of 
discounts were applied to close the first few deals. It may feel like it has been a free-for-all. Fix this by 
creating a firm discount table with defined trades (see below). 
 
Table 2.2​ Discount give-take list  
DISCOUNT/GIVE  ASK IN RESPONSE 
5%  Introduction to two prospective customers 
10%  Short use case video, tweet, or G2 Crowd 
(​www.g2crowd.com​) recommendation  
15%  2-year contract, paid annually upfront, speak at an event 
20%  2-year contract, paid upfront, host a workshop 
 
 
 
EXPERT ADVICE ​It’s easy to want to be involved in the details of each and every deal. 
But try to minimize micromanaging your AE as (s)he is pursuing a key deal. Your AE 
needs to learn from successes and failures the same way you did. However if they lose a 
deal, accelerate learning by debriefing together, and focusing on what can be improved. 
A win-rate of 1:5 offers four opportunities to learn from. 
JACCO VANDERKOOIJ 
Founder, Winning by Design 
 
31 
http://www.g2crowd.com/
 
Phase 3: Scale Up 
Congratulations! You have started to find your stride in sales with your first sales hire(s) in place. You likely 
have some ups and downs from month to month and your numbers can still sway above and below your 
monthly goal just from a large deal getting delayed. But generally, you’ve now reached around $5M in 
ARR. You know that there are a ton of deals “there”, but you also know that you could be doing much 
more as a company to capitalize.  
 
You’re starting to get some inbound deals from customer referrals, but as a founder, you’re still stretched 
thin trying to supplement those deals with additional inbound leads. You find that your calendar is quite 
busy: you’re speaking at specialized conferences and, over nights and weekends, you’re writing blog 
posts for the website.  
 
At this point, it’s time to start creating specialized roles in sales. Clearly, you will need a few more people 
to make this happen, which means that you may need a funding round. So, this is something that you 
should have on your radar well ahead of time to ensure that you prepare and get input from your investors 
and leadership. Once you start to create this specialization, your role as founder can start to shift away 
from acting as a contributor to spending more of your time managing and leading. 
 
 
Figure 2.3​ The organization starts 
to have specialized roles. The AE 
is now focused only on closing, 
you hire a CSM to cover customer 
success, and you hire an SDR to 
to generate and qualify leads. 
Each founder manages either 
pre-sales or post-sales. 
32 
 
In the previous phase, your AE was focusing on the entire pre-sale process, and one of the founders was 
managing the entire success and expansion motion.  
 
Remember, your ​first hire ​in the previous phase was your AE. In this phase, you should make the 
following hires:  
  
2nd sales hire: Customer Success Manager 
Why should this role be hired so early in the growth of the team? First, the numbers prove it works: As 
much as 75% of SaaS revenue comes from future years, and profitability in many cases only arrives after a 
customer has been with you for more than one year. Second, you need someone to learn from what is 
happening this year and help to build in best practices and improvements for the following year. And third, 
happy customers will generate new customers, keep churn low, and help to massively accelerate your 
growth.  
 
Knowing that, your CSM will handle the success and expansion of your customer base: they must ensure 
they are are satisfied with your product, and focus on reducing churn as much as possible. This person 
might be, say, one of your existing engineers who likes working with customers. It may also be one of your 
salespeople; they are often great CSM hires because they understand what customers are looking for. 
Another option for likely candidates is one of your first customers, or someone you met at an event or 
meetup who is really enthusiastic about what you are doing. This should be a person who is passionate 
about the product and understands what customers are looking for.  
 
3rd sales hire: Sales Development Representative (SDR) 
In this phase, your AE (previously covering the entire sales cycle up until the point of Commit) will now be 
overloaded with too many leads and not enough time to focus. So now is the time to hire an SDR who can 
cover prospecting and qualifying leads, so the AE can focus on closing.  
 
ThisSDR will follow up on inbound leads, and set up meetings for your AE. They should also help with 
demand generation by inviting people to join local events then follow up on those leads as well as perform 
targeted outbound on ‘low-hanging fruit’ opportunities (e.g., from trade shows). Over time, they may close 
some of the easier, more straightforward deals themselves. Ideally, they should naturally grow into and 
learn the AE role over time.  
 
   
33 
 
Common Questions 
 
Q: What are all of these different sales roles, anyway?  
A: Here’s a summary​ of the roles that you should expect to have as you grow your sales org:  
 
Table 2.3​ Summary of typical sales roles 
SALES ROLE  QUICK REFERENCE  FULL DESCRIPTION 
Market Development 
Rep (MDR) 
Inbound leads  Qualifies inbound leads, such as from your website or 
downloading a whitepaper 
Sales Development 
Rep (SDR)  
Inbound and outbound 
leads, initial qualification 
Proactive outbound prospecting to new leads; does initial 
qualification of leads prior to hand-off to AE 
Account Executive 
(AE) 
The closing role  Quota-carrying reps who close sales deals 
Customer Support 
Helps to resolve 
common issues 
Manages relationships with customer, provides admin support 
such as password resets, etc.  
Customer Success 
Manager (CSM) 
Manages customer 
accounts 
Manages customer accounts, ensures that customers are 
successful in using your product or service, and focuses on 
account expansion  
Onboarding Specialist 
(ONB) 
Onboarding new 
customers 
Handles the onboarding process for brand new customers to 
get them set up to a steady state of consumption of your 
product or service 
 
 
Q: Should I hire a VP of Sales first, before the AE?  
A: No. ​A VP of Sales must be focused on setting the strategy for the broader team, as well as to help 
close more complex deals. That’s where they should focus to help enable your company to scale - and 
keep in mind that the compensation of a VP can be that of two individual sales roles. So we recommend 
that you first establish the right roles and people to get your sales machine going, then hire a Director of 
Sales - but only once you achieve Phase 4 (see below). Once you are there, hire them in a director level, 
34 
 
and then have that person earn the VP title and role. And if they turn out not to be the right fit, then hire the 
right VP. 
 
Q: Should I have my AE prospect for leads?  
A: It depends. ​If you are selling large deals - such as selling $100K/year deals into Fortune 500 
companies - and your AE has to close only a few deals per quarter, your AE should be doing the 
prospecting as part of developing these accounts (networking, attending and organizing events, etc.). But 
if you’re selling smaller deals (e.g., $12K/year to small or mid-market businesses), and your AE has to 
close 3+ deals each month, he won’t have time to prospect in addition to working his opportunities. So it 
now requires a series of additional skills, such as outbound email and cold call techniques. Here you will 
need a two-stage sales cycle, where either a Sales Development Rep (SDR) performs the prospecting 
activities, or a marketing campaign generates inbound leads that the AE can follow up on.  
 
Common Pitfalls 
 
Pitfall 1: Not enough leads are generated. ​If that’s the case, then one of the following is happening: 
a) You are too early: Focus the SDR on organizing and creating a database of the right contacts to 
target. 
b) The SDR is not the right fit: They are not spending their time in the right ways. This role is highly 
activity based, and the SDR must put in the time to conduct a certain amount of each activity. As a 
general benchmark, it takes about 50-100 emails, 10-50 phone calls, and 10-100 profile clicks 
every day in order to generate the necessary number of leads. Sit down with your SDR and AE as 
a team and see how they feel about the progress. 
 
Pitfall 2: Too many “fluffy” meetings​. A lot of educating is happening on the calls, but leads are not 
entering the sales funnel. Spend two to three hours per day with the SDR, and help them understand how 
to prioritize and better qualify leads. Spend time coaching them on a few calls, and reviewing outbound 
emails and responses to inbound.  
 
Pitfall 3: Deals are not properly handed off. ​The SDR must provide a smooth hand-off to the AE. This 
includes making a proper email intro between the lead and the AE, as well as providing the AE with the 
right level of information. The AE and SDR should be meeting regularly (once a day) so that the SDR can 
provide background on the person, what they are interested in and why, and any other relevant points.  
 
35 
 
Pitfall 4: There seems to be a lot of interest, but nothing is getting closed​. This could be happening 
for a few different reasons:  
1) It’s an early market that has not yet fully developed. If that’s the case, be sure to stay 
hyper-focused on prospects who have a pain (a problem to solve), rather than everyone who is 
simply interested in your space. 
2) You have long sales cycles. In certain industries, buying may generally happen in a certain time of 
the calendar year. If you miss that window, that could mean a full one-year delay. If that’s the case 
for you, be sure that your sales team is hired six months before that window opens.  
3) Poor lead qualification or poor execution by your existing reps: Check that your existing team has 
the necessary industry knowledge and sales skills to be successful. See Chapter 5 for more on 
Skills. 
 
Understanding the Infrastructure You Are Building 
As you progress through the three phases of Start Up, Grow Up and Scale Up, you must start to think 
about how you want to set up your sales organization to scale beyond that point. Every company will be 
slightly different depending on your product and business model, but there are a few proven best practices 
and organizational structures that you can rely on, depending on your needs. 
 
Best practices for a scalable sales organization 
 
● Build your sales org in a phased approach; don’t try to hire entire teams all at once  
● Organize your team into PODs, where each team has a specialization 
● Decide if you are going to specialize geographically (e.g., New York, Los Angeles) or per market 
segment (e.g., by vertical): 
 
➔ Specialization based on geography is best for solutions that require salespeople to go 
on-site, and/or to have a strong relationship within the community. This most commonly 
involves high contract value selling, to the likes of large enterprises. 
 
➔ Specialization based on vertical is best for specialized solutions selling into a market that 
requires specific knowledge and insight; think of selling to financial institutions versus health 
care companies. Traveling to each customer would be expensive, so sales reps in this 
36 
 
model will often rely on online selling, supplemented with an in-person customer tour 
(anywhere from monthly to quarterly).   
 
● Clearly define roles for each member in the POD, such as: Account Executive, Practice Advocate, 
Customer Success Manager, Inside Sales Manager, Sales Manager, Customer Success Team 
Lead 
● Define how Sales will interact with other parts of the company. For example, Sales and Customer 
Success will work in concert on renewal vs. expansion sales. Another example: you should 
determine how and when Sales should provide the Product team with customer feedback and 
feature requests. 
 
Example: Phased approach to a scalable sales organization 
 
  
Figure 2.4​ The organization starts to specialize as 
inbound vs. outbound to support deal flow. As 
you start to run out of leads, SDRs need to 
develop and work campaigns in tandem with 
Marketing. On the other side of the customer 
journey, Customer Success starts to get 
overwhelmed by onboarding requests and isn’t 
spending enough time helping customers get the 
most value from the product with consistentusage. 
When this applies: Below $3M ARR 
 
Figure 2.5 ​The organization now starts to 
specialize in onboarding vs. customer success. 
The Success team is helping customers use the 
product, and is renewing monthly/annual 
contracts. But upsell activity is lagging, in 
particular from the big accounts that you had high 
hopes for. Your net revenue increase barely 
covers the churn.  
When this applies: ~$3M ARR 
37 
 
 
Figure 2.6​ The organization starts to specialize in 
deal size (most common) OR vertical markets. You 
will find that you can scale using this model. You 
will need VPs of Sales and Customer Success to 
manage these specialized motions and 
challenges. 
When this applies: ~$5M ARR 
Organize the team in a POD 
How does a POD work? ​In the example on the right, a 2x2 
POD is shown in which an MDR (Market Development Rep 
focusing on inbound lead development) and an SDR (Sales 
Development Rep focusing on outbound lead generation) 
are partnered with two AEs. The MDR/SDR combo sets up, 
say, 40 meetings for the AEs each month. From these 
meetings, the AEs might close eight deals per month. 
 
Why do PODs work well, and why should you use 
them? ​Team work, accelerated learning, motivation, mutual 
accountability. High velocity is based on proper deal 
handoffs.  
 
 
Figure 2.7​ The 
specialized 
roles are 
mapped into a 
POD 
How to model a POD. ​Historically, the efficiency of these PODs was not considered an issue due to 
more focus on winning logos rather than achieving profitability. But starting in 2014, the tides turned as the 
number of SQLs per SDR dropped from 20-30 on average to low 10s. Today, we know that for a POD to 
be economically viable, the annual on-target earning (OTE) of this POD should not exceed 40% of annual 
revenue. E.g., to generate $1M in ARR you should not exceed spending $400,000 in compensation; this 
includes base salary AND commissions. 
 
38 
 
Table 2.4​ POD Modeling 
EFFICIENCY  SPECIALIST  POD  Base+Variable=OTE  METRICS  DESCRIPTION 
 
MDR  
(Inbound) 
    500  MQLs 
1  $40K+$10K=$50K  5%  Conversion rate 
    25  SQLs (I) per month 
SDR 
(Outbound) 
1  $50K+$30K=$80K  15  SQLs (O) per month 
    40  SQLs (I+O) per month 
Jr.AE 
 
Sr.AE 
1 
 
$80K+$30K=$110K 
 
20% WR 
$10K ACV 
Wins three deals per month 
1  $100K+$40K=$140K  25% WR  
$12K ACV 
Wins five deals per month  
ONB 
(Onboarding) 
1/2  $50K+$20K=70K  8  Customers onboarded/mo 
    $96K  ARR per month 
  TOTAL  5  $415K  $1.162M  ARR generated / yr 
Table 2.5​ Example of different POD models and common uses 
STANDARD  INBOUND  OUTBOUND  TARGET 
 
 
 
 
 
 
 
 
Used for a regional 
approach, or large 
vertical market - e.g., 
one for the West coast 
and one for the East 
Used with an inbound 
business where lots of 
inbound leads are 
generated - often with a 
low ACV of up to $12K 
Used with an outbound 
approach, often 
platform sales, with a 
high ACV of $12-50K 
Going after a few 
hand-picked accounts 
valued $50-250K ACV 
with a dedicated team.  
39 
 
How to grow PODs? ​As your revenue grows, your PODs will start to multiply. Each POD is responsible 
for a dedicated revenue flow. The more PODs you set up, the more stable your revenue growth becomes. 
 
Figure 2.8​ Visualizing how your sales org scales over time 
   
40 
https://www.lucidchart.com/documents/edit/6ae29736-7a47-4a22-a57e-1bb10706b193/0?callback=close&name=docs&callback_type=back&v=220&s=612
 
How to use PODs to run sprints to identify target markets? ​One of the key advantages of PODs is 
the realization that you can quickly refocus your resources depending on the market; this is very important 
during the early days of scaling revenue. In the example below, you will notice the specialization over time - 
we call these sprints. The POD will heat-check specific verticals/regions/segments. This allows each POD 
to train only on the needed use cases/value proposition for each sprint. The sprints can vary in length, 
anywhere from 30 to 90 days. 
 
 
 
Figure 2.9  
This shows the use 
of PODs to 
heat-check a 
market by sprinting 
through a series of 
verticals, such as 
regions or market 
segments 
 
Example of how to structure a sprint over time: 
● First two days: Train the team on use cases, and role-play a variety of scenarios 
● First week: Pursue B-leads first to get familiar with responses, meet up and share best practices  
● Second week: Market and organize an event, pursue your A-leads to attend 
● Third week: Pursue A-leads, host events, follow-up with event attendees 
● Fourth week: Wrap up, learn from best practices by measuring what worked, start next sprint 
 
   
41 
 
How to scale your staffing? ​We have found that PODs also allow you to scale your recruiting. Meaning, 
a new POD can be launched by promoting the top performer of an existing POD (e.g., AE of POD 1) to 
become the new POD leader of POD 2. The team leader of POD 1 can backfill the position within the POD 
and hire a new MDR. 
 
 
Figure 2.10 
Stabilizing the 
growth of your 
sales team: the top 
producing POD 1 
does not get 
disrupted while 
POD 2 is being 
built. POD 2 is built 
from the ground up 
with a top leader 
that sets the stage. 
 
 
 
   
42 
 
   
43 
 
   
44 
 
 
 
 
 
 
 
 
 
CHAPTER 3 
THE SALES PROCESS 
 
 
 
   
45 
 
Let’s start by creating a very simple sales process. Different sales teams may use different words to 
describe the steps in their process, but the generic process below covers the vast majority of all sales 
processes out there. Notice how this process is customer friendly, in that the activities are described from 
the point of view of customer value - not from the perspective of a sales person trying to hit quota. 
 
 
Figure 3.1  
Standard 
Customer-Centric 
SaaS Sales 
Process 
 
In this sales process, you can see three different areas: 
● Prospecting (in red), with three sources of opportunities: Outbound, Inbound and Targeted 
Accounts 
● Sales process (in blue), with the classic steps of your conversation with the customer 
● The beginning of the Customer Success process (in green) 
 
Not every Go To Market model needs the exact same sales process. In fact, there should probably be 
slight differences between them depending on the segment or type of customer. In the table below, you 
46 
 
can see how sales activities across the sales process can vary, depending on which type of target is 
concerned. 
 
Table 3.1​ Applying the sales activities  
CLIENT  VSB/ 
ProUsers 
SMB/ 
Teams 
MID-MARKET/ 
Departments 
ENTERPRISE 
Methodology 
(sales cycle) 
Transactional 
(secs/mins) 
Solution 
(days/weeks) 
Consultative 
(weeks/months) 
Provocative 
(months/quarters) 
Prospecting  Inbound  Outbound  Target   Identify 
Hand-off  CRM  CRM + Email  1:1 Meeting  1:1 Meeting 
Diagnose    Impact/Critical 
Event 
Decision  
Process  
Provoke 
Prescribe 
Trial 
Standard Demo 
Custom  
Demo 
Workshop 
Assist  Decision  
Criteria 
Proof of  
Concept 
Recommend  Quote  Proposal  Business  
Case 
Trade  Buy  
Online  P/O 
Trade  Negotiate 
Commit  Contract  + SoW 
Go Dark  Nurture  Outbound  Alerts  Provoke 
Onboard  Enable  Install  Integrate  Onboard 
   
47 
 
How to Create Your Own Sales Process & Sales Playbook 
No matter what stage your company is in, you must have a clearly defined sales process and playbook. 
Success in SaaS sales requires measurement, and measurement requires that you be methodical. So 
creating your documented sales method allows you to: 1) provide consistent guidance to your sales reps 
on how to progress through their deals, 2) conform your activities to a process that you can easily 
measure, and 3) understand what’s working and what needs adjusting. 
 
STEP 1.​ ​DETERMINE WHICH SALES PROCESS  
Determine the sales process best suited for your business from Table 3.1 (make modifications as needed) 
 
STEP 2.​ ​MAP OUT THE STAGES  
Map out thestages of your Sales Playbook. See Table 3.2 
 
STEP 3. DEFINE THE STAGES 
For each stage, you should define the following:  
 
● Goal: Description of what needs to happen at that stage 
● Actions: A few simple actions per stage that the sales rep should take in order to get clear insight 
into the customer situation 
● Enable: Enablement tools available to assist the process (documents, references, team members 
to bring in) 
● Outcome: The single outcome that should result from the actions taken (often a confirmed 
meeting) 
 
Now let’s see what you should keep in mind depending on which of the three phases your business 
currently falls under. 
 
 
 
   
48 
 
Table 3.2​ A snapshot of a generic SaaS Sales process 
 
 
Stage 1 
HANDOFF 
 
Stage 2 
DIAGNOSE  
(QUALIFICATION) 
Stage 3 
PRESCRIBE 
(NEEDS 
ANALYSIS) 
Stage 4 
ASSIST 
(VALUE PROP) 
Stage 5 
RECOMMEND 
(PROPOSE) 
GOAL  Secure a meeting 
with a prospect 
who fits the 
profile and has a 
pain. 
Diagnose the pain, 
identify the urgency 
and determine if 
you can help them. 
Navigate the org 
and keep 
educating by 
providing materials. 
Assist the 
customer through 
the decision 
process. 
Create a proposal 
outlining price and 
impact it will have 
on the prospect’s 
business. 
ACTIONS  1. Prepare 
- SDR handoff 
- Call before the 
call 
- Situational 
questions 
- ​Pain questions 
2. Confirm 
Situation 
- ​Situational 
questions 
- “Did I get that 
right?” 
3. Determine 
Pain​ - ​Emotional/ 
Rational 
1. Prepare 
- Research 
situation 
- Identify 
Use-cases 
2. Have Meeting  
3. Discovery 
- Get ​Critical event  
- Establish ​Impact 
 
 
1. Decision 
Makers 
- Identify ​Decision 
process 
2. Educate/Demo 
- Top three Pain 
Points 
- Ballpark pricing 
3. Drive a 
decision  
- Establish a 3 x 3 
1. Decision 
Criteria 
- Identify ​Decision 
criteria 
- Identify ​impact​ of 
each criteria 
2. Decision 
Process 
- Hierarchical or 
consensus? 
- Chronological 
steps 
1. Propose 
- Develop ​proposal 
- Schedule review 
call 
2. Orchestrate 
- Set up a refer call 
- ​Involve execs  
- Involve Customer 
Success 
ENABLE  - WBD Research  
- WBD QCards 
- WBD Discovery 
 
- WBD Demo 
- WBD Account 
Plan 
-​ WBD Decision 
criteria 
- WBD Decision 
Process 
-​ WBD Proposal 
 
OUTCOME  Scheduled a 
discovery meeting 
Scheduled a 
custom demo 
meeting with 
decision makers 
Scheduled a 
decision criteria 
review meeting 
 
Scheduled a review 
of the proposal  
Proposal sent and 
reviewed; schedule 
meeting with buyer 
49 
 
Phase 1: Start Up 
In this phase, it is unlikely that you have a CRM and are probably storing sales activities on a spreadsheet.  
 
 
Figure 3.2 
A simple “solution” sales process 
to use as a baseline while in the 
Start Up phase 
 
Commons Questions 
 
Q: When should I start creating my first process and playbook?  
A: After the first 10 deals.​ Update it after 20, 30, 40, 50. Then it should be stable up to about 100 deals.  
 
Q: How many stages should my process have?  
A: No more than 10. ​Remember not to over-engineer a process; that’s the enemy of a sales rep’s time.  
 
Q: Should I start from scratch?  
A: You could for the first 10 deals, but why? ​We provide a proven template for you to work from (see 
above) that has been created based on the learnings from hundreds of companies that came before you.  
 
Commons Pitfalls 
 
Pitfall 1: No process. ​In Founder Sales mode, you keep winging it. Every deal closes differently. To you, 
it’s pretty clear but to others, it’s a mystery. So how do you establish your first process? Do a search 
across your email and calendar for the customer’s name and root name. This provides a history of how the 
50 
 
relationship was started and meeting you had. See if you can glean some themes or common language 
across these deals.  
 
Pitfall 2: Self-centered process. ​Looking at your sales process, it feels sales-y (e.g., “Qualify, Demo, 
Negotiate,” etc.). It may seem like semantics, but reps absorbing guidance like this will add up to a 
company that wants something but gives little - and ultimately will have unhappy customers. The best way 
to solve this is to look at the key actions in each phase and ensure they provide real value to the customer. 
For example, instead of “Qualify” say “Diagnose” and then teach your team how to diagnose the 
customer’s pain by asking the right kind of diagnostic questions. Qualifying, on the other hand, will often 
be more focused on determining the customer’s situation, and it won’t help the sales rep get to the 
customer’s true underlying issues. 
 
Pitfall 3: Overly detailed process. ​Over-designing a sales process will kill deals. You don’t need to 
identify every step and criterion. That will soon translate into dozens of fields to be completed in your CRM, 
and before you know it, your sales reps have basically turned into accountants and are spending little time 
talking with customers. 
 
Phase 2: Grow Up 
 
In this phase, you’re outgrowing the spreadsheet and you need to implement your first CRM before things 
get out of control. Your CRM at this stage can be something like HubSpot (free) or ProsperWorks (G 
Suite-based). You may not be willing to commit to something like​ ​Salesforce quite yet, as it often requires 
a significant amount of time and resources (usually a Salesforce consulting partner) to set up. 
 
51 
 
 
Figure 3.3 
Scaling up the 
sales process to 
focus on outbound 
and become more 
customer-centric 
Commons Questions 
 
Q: Should I just get Salesforce already?  
A: No, use a simple CRM to start.​ We recommend holding off at this stage. Right now, your process is 
not 100% set yet because there is still more to learn as you build up your sales team. You need flexible, 
simple tools that are easy to manage at this stage; see Chapter 4 on Technology for more details. Learn 
from those before you: For every change that you need to make to Salesforce CRM, you often need to 
make many others. Talk to anyone in Sales Ops who has implemented SFDC at their company, and they 
will tell you that it gets real involved, ​real fast.  
 
Q: Should I hold my team accountable for executing the process?  
A: As much as possible, but as little as needed. ​You need to be flexible to change. Review and 
update the process every quarter to make sure that it’s still meeting your needs. Use recordings (calls, 
demos, etc.) to streamline the process as much as possible.  
52 
 
Commons Pitfalls 
 
Pitfall 1: You are not analyzing your deals against a process. ​You keep winning deals, but you’re not 
going back to learn why the customer bought your solution, how you can continue to replicate that, and 
how you can improve their experience.  
 
Pitfall 2: You are hiring a sales rep and think they should be able to do it. ​Your first sales person will 
have experience in sales, but likely doesn’t have much experience building a sales process from scratch. 
Sit down together for a few hours and build the sales process with your sales rep in a Google 
slide/doc/sheet. Your knowledge of the customer plus the rep’s knowledge of efficient sales will both 
contribute to a better process. 
 
Pitfall 3: You are selling to several different types of customers. ​At this stage, it is important to really 
focus on the type(s) of customers that you want to want to serve. For example, if you are still selling to 
everything from individuals to global companies, then you are quickly going to see that your resources are 
spread too thin. You will run the risk of doing a mediocre job serving too many segments, rather than an 
excellent job knowing and serving a more focused customer segment. Be sure that you have become 
purposeful and consistent in determining your target users that you want to serve. 
 
Pitfall 4: You are closing deals but not providing any support post-sale. ​Customer success 
post-sale is just as important (if not more so) than the sale itself. If you don’t yet have any dedicatedSuccess team members, make sure you work out a plan with your product/engineering team for how to 
address customer issues that come up.  
 
 
EXPERT ADVICE ​Avoid exporting the data to a spreadsheet or slide and using that for 
reporting. Both for internal meetings with your team and for board meetings, you should 
use reporting from your CRM. This may take a bit more time in the beginning to get used 
to it, but it avoids days of chaos and panic the week before the board meeting, as you’re 
getting your numbers straight from the source.  
JACCO VANDERKOOIJ 
Founder, Winning by Design 
 
Pitfall 5: You’re using the wrong process. ​In general, when a prospect reaches out to us on our 
website, we respond with a series of actions. These include: Call them, leave a voicemail, send an email. 
We know time is of the essence, and many companies aim to do these actions within minutes. But what 
53 
 
we found is that this time-sensitive approach is often used in the wrong situation. To clarify: A prospect 
downloads a detailed research paper on your website by providing their email address in a form. This type 
of lead is often wrongly categorized as an inbound MQL. But the SDR calls the person immediately, leaves 
a voicemail and sends a follow-up email, as if the prospect has already expressed a pain. But they never 
did! The prospect feels intimidated by the assertive follow-up. So clearly, not every inbound lead (MQL) is 
created equal. This MQL should have gone into the outbound process where research should have been 
performed to determine if this prospect has a pain. 
 
 
Figure 3.4 
Fit and Pain are reversed on 
inbound vs. outbound processes, 
resulting in the wrong action 
  
Table 3.3​ The difference between “true inbound” and “quasi-inbound” leads 
TRUE INBOUND  QUASI-INBOUND 
● Talk to sales 
● Schedule a demo 
● Contact us 
● Download an online asset 
● Sign up for a webinar 
● Visit the pricing page of the website 
Being quick is the most important. 
 
Next step:​ Inbound Process. 
Being relevant based on research is more important 
than being quick. 
Next step: ​Outbound Process. 
   
54 
 
Phase 3: Scale Up 
In this phase, you need to get your process and CRM secured.  
 
 
Figure 3.5  
The process adds 
targeted account 
outreach, which is 
often associated 
with provocative 
selling. In this 
phase, the sales 
process now 
extends to 
customer success 
for a full 
customer-centric 
relationship with 
each account. 
   
55 
 
This is a time to invest in doing it right, as you are now building the platform that you will use to scale. Your 
metrics need to be locked and dashboards ironed out. You may also realize that you are now addressing 
new segments, such as selling to mid-market from only SMB before. Each of these new markets need to 
go through the same development of your sales process: Win your first 10 deals, then establish a process, 
then update the process with the next 10 deals, up to 50 deals, and so on. 
 
Common Questions 
 
Q: Should I create a different process when I sell into a different segment? ​If I use one sales 
method (consultative) to sell to SMB and I am moving up-market to sell to larger companies, should I 
change my sales process?  
A: Yes, most likely. ​Selling to mid-market is a very different sale in that it requires more people to 
approve the process, the sales cycle is often longer, and they have a more structured purchasing process. 
You will need to adjust your sales stages, timing, and tactics at each step so that you can add value in this 
new type of process. 
 
Q: Should I just get Salesforce? 
A: Probably.​ You should also discuss with your peers in your specific industry or niche market to learn 
what they have seen.  
 
Q: What should be on my CRM dashboard? 
A: We have created a sample dashboard in the Annex for you. ​Use that to get you started.  
 
Q: What should I spend on a CRM/process consultant?  
A: Somewhere between $5K-10K​ to set up your CRM and create dashboards. They will need to know 
your process, so make sure you have your playbook ready. 
 
   
56 
 
Common Pitfalls 
 
Pitfall 1: You keep the same sales process. ​Don’t make this mistake. New segments behave 
differently from others and you need to continue being customer-centric by making your sales process fit 
each segment.  
 
Pitfall 2: You want to set up your CRM yourself. ​Yes, of course you’re capable, but this is not the 
time. If you’re setting up SFDC, you should bring in a proven SFDC consultant who can help you get it 
right the first time, and avoid redoing it (and all of the headaches that come along with that) later on.  
 
Pitfall 3: You want to use a niche CRM. ​Commit to a standardized CRM that provides the best 
infrastructure. The extra unique customization that you might get from a niche CRM doesn’t even come 
close to the benefit that you get from installing a CRM that is easy to use and familiar to your sales reps 
and sales operations. 
 
   
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58 
 
 
 
 
 
 
 
 
 
CHAPTER 4  
TECHNOLOGY STACK 
 
 
   
59 
 
The tool stack that you choose to use is just as strategic as the organization and the processes that it 
supports. And it can get overwhelming very quickly. There are literally thousands of options to choose from 
for all of the various tools your team will need. 
 
In general, we see two common options: 
 
AN SFDC-BASED INFRASTRUCTURE  A GOOGLE-BASED INFRASTRUCTURE 
Using Salesforce as a CRM, with all of the SaaS 
services available in the Salesforce App Exchange. 
This sales stack is most commonly used by 
companies that have an Annual Contract Value of 
$15,000 or more. Often a platform product, and 
often longer sales cycles that need a robust 
toolset. 
Using tools based on G Suite (Google products) 
with their apps on it. G Suite is commonly used 
with early and high velocity solutions. Companies 
that sell applications (rather than platforms) tend to 
use a G suite infrastructure for longer before 
switching to SFDC.  
 
Luckily, there are a few key guidelines that you should follow that will help narrow down the field to point 
you in the right direction toward an effective tool stack.  
 
#1 Know the difference between the layers of the stack  
● Server​: You need servers for the operations of your business. In general, the major players you will 
be selecting from are Microsoft, AWS and Google.  
 
● Platform​: Once you choose a platform, recognize that it can be tough to switch in the future. So 
be sure to do your research on platforms and ensure that you choose those that will allow for your 
dependencies. Think of Salesforce, Hubspot, Marketo or Zendesk.  
 
● Application​: Applications can be stand-alone, fully integrate into your platform, or work 
side-by-side. Applications can be exchanged more easily if your business needs change and grow. 
Think of Calendly, Bill.com and Zoom.  
 
● Outsourced Services​: These are external services that will perform an entire function for you. 
Think of an outsourced SDR, or an outsourced lead enrichment service. 
60 
 
 
#2 All tools should contribute data to the database 
Since many of your decisions in the future of your company will be data-driven decisions, we want to make 
sure that all tools contribute data to your knowledge base. Take the example of an email automation tool. 
Instead of asking sales people if they are effectively using email, make sure you are using an email tool 
where you can simply see the answer with data. Meaning...your email automation tool automatically logs 
all inbound and outbound emails, and produces response and deliverability metrics for those emails. In 
general, even if a specific tool is functionally better than another, we recommend that you keep looking if it 
does not contribute actionable data to your collective organizational database.  
 
#3 Contracts with different types of technology should be treated differently 
● Servers: The infrastructure you are buildingon. This commonly is either Microsoft or Google server 
infrastructure. 
● Platforms: After an initial one year contract, you should feel comfortable to strike a multi-year 
commitment if the platform suits your needs 
● Applications: Use a maximum term of 12 month agreements, and renew annually 
● Services: These should have contracts based on usage or impact; make commitments of no more 
than three months at a time 
 
#4 All functions need to be supported by tools, but be sure to keep it balanced 
Every function needs some amount of tooling in order to scale. But take care: it’s easy to load up the 
marketing department with many tools while customer success has less support. Be sure to avoid this. 
The more tools you have, the more manpower you need to manage and administer those tools, as well as 
interpret the data and insights that those tools provide. Make sure that you strike a balance between tools 
and human brain power. 
 
   
61 
 
Recommended Sales Tool Stack 
 
One of the questions that we are asked most often is, “What tools should I buy? I don’t want to go 
through a long vetting and selection process. Can you just tell me which ones are good?” The answer to 
that is - it depends. It would be very easy to point to the ‘best’ tool for lead generation or the ‘best’ tool for 
proposal creation - but that simply wouldn’t be serving the needs of your business. Why? Because the 
needs of every business are different. This is why there are so many tools out there that all have different 
capabilities and feature sets.  
 
With that said: We can’t say that the tools listed below are the “right” ones for everyone. This list is meant 
only to be a starting point - a gauge to help point you in the right direction - so that you can evaluate other 
tools from there and make a selection based on what fits with your business. And keep in mind that new 
amazing solutions are cropping up all of the time, and point solution tools get acquired by larger 
companies every year, so this list is by no means conclusive or exhaustive. 
 
For some great resources and further details and tool reviews, check out:  
● The 2017 Startup Sales Stack Report from Bowery Capital 
(​https://bowerycap.com/blog/sales/2017-startup-sales-stack-report/​) 
● Sales Hacker Best 160+ Sales Tools: The Complete List, 2018 Update: 
https://www.saleshacker.com/sales-tools/ 
● G2 Crowd Sales Software reviews: ​https://www.g2crowd.com/categories/sales  
 
But before we get into the details, let’s set the high-level baseline first for what is needed in each phase of 
growth.  
 
Phase 1: Start Up 
In the Start Up phase, you have only a couple of sales reps. You don’t need to overburden yourself or 
them with too many tools. The guideline here is to do as much as you can with simple spreadsheets, and 
supplement with just a few hard-working tools: you should enable prospecting with tools like LinkedIn 
Navigator, MixMax and Calendly, and for most other tools, you can use manual/spreadsheet substitutes.  
 
62 
https://bowerycap.com/blog/sales/2017-startup-sales-stack-report/
https://www.saleshacker.com/sales-tools/
https://www.g2crowd.com/categories/sales
 
 
Figure 4.1​ Most startups use Google G Suite to start building their tool stack: it’s easy, relatively low cost, and 
strong in sharing capabilities. 
 
Google G Suite:​ Provides cost effective access to classic office productivity products. You will quickly 
become addicted to the ease of their products and the ability to share, edit, comment and collaborate in 
real time. You will start to play around with your first applications that can operate on top of or integrate 
with Google G Suite: 
 
● ZoomInfo: ​Over the next few years, you need to build a high quality database, which means that 
you need to use high quality inputs. ZoomInfo provides reliable contact information for your target 
prospects based on the parameters that you set.  
● Drift*:​ As you are building up visits to your website, you should start engaging with those visitors. 
Drift allows you to chat with them. Here you can use the Drift bot to quickly answer questions, 
book meetings and gather insights. We recommend that you implement this as early as possible 
(freemium version). 
● LinkedIn*:​ Rest assured that LinkedIn for both understanding who you are meeting with, as well 
as lead generation, will be a reliable and valuable source of information. 
● MixMax*:​ As you are getting your sales team started, you will need to do a lot of scheduling, 
sending templated emails, and a bit of email cadences. MixMax offers all of this in a very 
user-friendly way, so that you can be incredibly efficient with your email outreach. 
63 
 
● Zoom Conference: ​While in-person meetings are incredible valuable, it won’t help you scale to be 
where you need. So start to use and get comfortable with remote meetings via video conferencing 
with Zoom as quickly as possible.   
● HelloSign/DocuSign: ​You need to maintain an electronic record of your electronically-signed 
documents and agreements from day one. Use a freemium subscription until you are exceeding 
the amount of free signatures, and then move to a paid subscription. We recommend that with 
whatever provider you choose, stick with it for at least a few years. 
● Xero: ​Don’t attempt to send your first invoices manually; just immediately start using Xero. The 
complexity of doing this manually and the mistakes that occur with financial transactions simply 
aren’t worth the small amount in savings. See below for an example of a customer-friendly invoice. 
Note that this early stage is the time to give your direct phone number so that you can resolve any 
financial issues quickly. 
 
Hello ​<First Name>​, 
 
Thank you for your business, it means the world to us! Please find invoice ​<invoice number>​ for ​<invoice 
amount>​ due on <​due date​>. You can view your bill online here: <​insert link​> 
 
If you have any questions, please do not hesitate to contact us. 
 
Thank you from all of us at <​Company Name​>. 
<​Your Name​> | <​your telephone number​> | <​your email address​> 
 
 
Common Pitfalls 
 
Pitfall 1: Commiting to payment/contract terms that are too long. ​We strongly recommend that you 
first go with monthly, even if it is more expensive. If the tool proves to be impactful, then move to an 
annual/upfront contract. Do not agree to auto-renewal! 
 
Pitfall 2: Jumping right into paid subscriptions when a free version is available.​ This is the time to 
test and learn. There will be plenty of other tools that you will want to buy over time. 
64 
 
 
Pitfall 3: Not using a tool for critical tasks such as document signing, or web conferencing. 
These are critical tasks that you should not execute with free tools. 
 
Pitfall 4: Buying into a CRM/MAS right away when you don’t even have 10 customers yet.​ Don’t 
invest in an expensive subscription before you need it. Also, consider that you will need someone to 
implement and manage a CRM - it doesn’t just run itself! 
 
Phase 2: Grow Up 
In the Grow Up phase, you will have outgrown your heavy reliance on spreadsheets. Here you should 
implement a lightweight CRM, enhance your lead qualification with lead enrichment and analytics, and 
start to use the paid versions of some of your tools, rather than just getting by with the free versions. You 
will quickly see how the extra spend will be worth the efficiency gains as you scale. 
 
 
Figure 4.2​ In the Grow Up phase, Marketing Automation and CRM platforms come into play in your tool stack. 
 
You’re growing, so now is the time to commit to your first platforms: 
● HubSpot/Pardot: ​Use this for your Marketing Automation system so you can build landing pages, 
track content engagement and manage your first “newsletter-like” campaign 
● Pipedrive: ​This is a popular CRM system that easily plugs into your Google infrastructure, though 
some may prefer to stick with Hubspot and use their CRM solution  
 
You are movingfrom freemium subscriptions to paid subscriptions:  
65 
 
● Drift​: Start using playbooks per page (includes campaigns, qualification and scheduling) 
● LinkedIn: ​Pay for the premium subscription (Sales Navigator); it provides advanced lead search 
and lead recommendations 
● Zoom: ​Move to a paid license and start investing in a proper ‘Zoom Room’ (Zoom-equipped 
conference room with integrated audio and content sharing). No more kitchen table or bedroom 
video conferencing! 
 
At this phase, you may find yourself starting to use your first outsourced services: 
● External Accountant: ​It is probably time to have an accounting firm perform your invoicing and 
chase down payments. You can now hire a qualified external accountant who logs into your Xero 
account remotely, and immediately take that burden off your shoulders. 
● Lead Enrichment​: In the first phase, you were surfing websites, LinkedIn profiles, and 
government sites to find leads - all of this can be outsourced. An easy way to hand this off is to 
create a screen recording with a voiceover where you show and talk through how you generate 
these leads, and you can outsource it by finding a person on a platform such as Upwork. Give the 
person you hire the video so that they can see exactly what they should do.  
 
 
EXPERT ADVICE ​There are a few helpful ways to make an Upworker successful. First, 
record a short video or detailed write-up of the work you want them to do. Next, outsource 
the work to three to five people on Upwork who meet your experience and location criteria, 
and review their work after a paid trial period. Hire whichever person did the best job. Solid 
work product plus excellent communication (both style and responsiveness) will be present 
in the best candidates. 
SARI EISENDRATH 
Sales Enablement, Winning by Design 
Common Pitfalls 
 
Pitfall 1: How to decide on a tool? ​There are basically three areas of impact from a tool set: 
1. Be more effective: win more deals (think of tools such as Infer or Everstring) 
2. Be more efficient: do the same amount of work with less resource (for example, Calendly) 
3. Have a better experience: There are two different points of view: 
66 
 
a. Customer has a better experience: Think of Docusign and how easy it is for the customer 
to execute a document 
b. Improve the operator experience: Think of a tool that helps people avoid having to 
endlessly enter data - such as an accounting tool like Xero, or a quotation tool like 
Pandadoc 
If a tool provides impact in all three categories, GREAT. If in two, GOOD. If just in one, it better be one 
heck of an impact to justify purchasing it! 
 
Pitfall 2: You are not sure how to choose, there are so many options for tooling. ​A/B test over a 
period of one to two weeks, then choose. 
 
Pitfall 3: You pick an excellent tool, but it doesn’t integrate with your existing stack. ​Don’t do it. 
 
 
   
67 
 
Phase 3: Scale Up 
 
In the Scale Up phase, you will now have a sizeable sales team, and you will need a more robust toolset to 
enable your team and orchestrate more sophisticated activities. This becomes very important now that you 
will be adding more sales reps at a much faster rate compared to sales operations/enablement and sales 
managers. You should be implementing tools that can provide sophisticated insights and enable you 
across the full customer lifecycle. 
  
 
Figure 4.3​ In the Scale Up phase, you should introduce a customer database and upgrade to industry-grade tools 
 
Platforms: ​You need to implement the infrastructure that will likely stick with you until $50M ARR. So 
choose wisely! 
● Customer Database: ​Use Salesforce. It’s expensive and it can be cumbersome, but it’s the most 
scalable. 
● Marketing Automation System: ​Inbound companies (applications) often pick HubSpot, whereas 
outbound companies (platforms) often pick Marketo. You need a platform that provides detailed 
data on amount of leads, where they came from, how they engaged with your company and what 
content they have consumed. 
● Customer Relationship Management:​ Use Salesforce (see above). 
68 
 
● Customer Platform: ​You likely will use a combination of Zendesk (ticketing) and may add 
Gainsight or Totango on top of that for customer success. 
 
 
EXPERT ADVICE ​One of the keys to picking the right tool is determining if it integrates 
with your data model. For instance, is a call recording automatically added to the customer 
record in your CRM, or does the sales rep need to do that manually? Look out for these 
seamless integrations to complete your data model.   
JULIE WEILL PERSOFSKY 
Sales Architect, Winning by Design 
 
Applications: ​You likely now have several different teams with different needs and different asks for the 
applications they want to use. You need to start prioritizing what deserves your investment. 
● Cloud-based proposals: ​Build proposals, add terms and conditions, and use real-time updated 
customer lists with a tool like PandaDoc 
● Cloud-based phone system:​ You can no longer just be an “email company with cell phones” so 
it is time you put in a phone system, 1-800 line, etc.; use a cloud provider like TalkDesk or 
NewVoiceMedia 
● Real-time dashboards for board-level reporting:​ It is time to stop driving your organization 
crazy at every board meeting; instead, use reporting directly from standardized dashboards, using 
a solution such as InsightSquared 
Outsourced Services: ​At this point, you can add extra services to cover your weaknesses. Some of 
these use their own tools: 
● Call reviews/coaching: ​To improve sales performance, you can start using a tool such as Chorus 
or Gong, which will record calls and provide call analysis. These services directly integrate with 
Zoom calls. To analyze the recordings, you can work with an outsourced service such as Winning 
by Design to perform call reviews for you - ensuring your sales metrics such as ACV, win rate and 
sales cycle are in the top 10 percentile. 
 
   
69 
 
Common Pitfalls 
 
Pitfall 1: How to avoid an overload of tools? ​Any tool that involves a multi-month contract should 
require approval from your executive team. This is important, as every tool requires an investment from 
your team of time, training, budget - or a combination of all of these.  
 
Pitfall 2: It is so easy to load up on tools...how many SaaS tools is right? 
Note: Numbers below are the for entire company, not just for the sales organization  
● Start Up: 10-20 tools 
● Grow Up: 20-30 tools 
● Scale Up: 30-50 tools 
 
Pitfall 3: Loading up on tools without having enough manpower to run them. ​You will need at least 
one (if not a few) people who are dedicated to Sales Operations to manage your tool stack. As easy as 
these providers make it seem that you can just plug and play, you will need someone to manage the 
process of vetting, running pilot tests with your sales reps, selecting, integrating, and managing.  
 
 
  
   
70 
 
With all of that said, here are even more granular recommendations for each type of tool in each phase.  
 
Table 4.1​ A starting point for tools to think about about at each phase of growth.  
Note: ​(G)​,​(M) ​,​(S) ​ indicates where a tool is strong with G Suite, Microsoft, or Salesforce, respectively.  
  START UP  GROW UP  SCALE UP 
Account-Based Sales & Marketing 
Social selling platform: 
LinkedIn 
Must have  Sales Navigator is nice 
to have 
Sales Navigator is a 
must have 
Analytics 
Reporting & business 
intelligence 
Spreadsheet  CRM built-in 
dashboards 
InsightSquared 
Communication / Conferencing 
Internal office collaboration  Slack   Slack  Slack 
Contact center/phone 
system 
Your own cell phone 
with Google Voice 
Your own cell phone 
with Google Voice 
TalkDesk/New Voice 
Media 
Conference calling/online 
demo 
Zoom (Basic/free)  Zoom (Pro)  Zoom (Business) 
Call recording & analysis  -  Apple Quicktime  Gong, Chorus, or 
Refract 
Online chat: DriftFree  Standard (custom 
greetings) 
Pro (bot play books, 
auto CRM) 
Content Sharing & Management 
Collateral management  G Suite  G Suite  G Suite 
   
71 
 
[CONTINUED] ​Table 4.1​ A starting point for tools to think about about at each phase of growth.  
Note: ​(G)​,​(M) ​,​(S) ​ indicates where a tool is strong with G Suite, Microsoft, or Salesforce, respectively.  
  START UP  GROW UP  SCALE UP 
Contract Lifecycle Management 
Proposal creation  G Suite  G Suite  Pandadoc 
Document execution  Freemium product 
(HelloSign) 
DocuSign (shared 
license) 
DocuSign (group 
license) 
Contract & billing  Xero  Xero  Xero 
Customer Relationship Management (CRM) 
Customer Relationship 
Management (CRM) 
Google Sheets​(G)​/ 
Pipedrive​(G) 
Hubspot Free​(S)​/ 
Pipedrive​(G) 
Salesforce/ 
Pipedrive​(G) 
Customer success  DIY  Build into the 
product (e.g., insert 
Intercom) 
 Gainsight/Totango 
Marketing automation  -  Hubspot  Hubspot/Marketo 
Support ticketing  -  -  Zendesk 
Lead Generation / Productivity / Prospecting 
Prospect identification/lead intel  ZoomInfo  ZoomInfo  ZoomInfo 
Online lead generation  LinkedIn  LinkedIn   LinkedIn Sales 
Navigator 
Lead enrichment  DIY  Offshore  Offshore 
Predictive analytics & lead scoring  -   Infer/Everstring  Infer/Everstring 
 
 
72 
 
[CONTINUED] ​Table 4.1​ A starting point for tools to think about about at each phase of growth.  
Note: ​(G)​,​(M) ​,​(S) ​ indicates where a tool is strong with G Suite, Microsoft, or Salesforce, respectively.  
  START UP  GROW UP  SCALE UP 
Predictive analytics & lead scoring  -   Infer/Everstring  Infer/Everstring 
Outreach/Prospecting  MixMax​(G)  MixMax​(G) 
Outreach​(M) 
Salesloft​(S) 
MixMax​(G) 
Outreach​(M) 
Salesloft​(S) 
Productivity 
Calendaring  Calendly (Basic/free)  Calendly (Premium)  Calendly (Pro) 
Sales & Market Intelligence 
Competitive intel    Owler  Owler 
General 
Server Infrastructure (Mail, 
Calendar, Drive, etc.) 
G Suite  G Suite  G Suite 
Build a tool stack  Not really  Start doing it  Must have it; 
formalize it on a 
poster 
 
 
   
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74 
 
 
 
 
 
 
 
 
 
CHAPTER 5 
PROFESSIONAL SKILLS 
 
   
75 
 
Many founders make the mistake of thinking that the team in place from the very beginning will be the 
same team they need when the company grows into a billion dollar company.  
 
Each phase of the company requires different skills. This is of course not to say that you need a different 
team at each phase - your team members can certainly grow their skills with the needs of the business. 
But founders must think about how to recruit for the current phase, and also look ahead to the next phase 
and the potential business and skill needs.  
 
These are the high-level qualities and skills, by phase, that you should be looking for and recruiting in 
candidates:  
 
● Start Up:​ Self starter, reliable performance, proven superstar, might dislike process, will help to set 
the tone of the culture you are looking to establish 
● Grow Up:​ Loves to create a process and document what they are building, able to listen and learn 
from what goes around them, enjoys working with and learning from small teams 
● Scale Up:​ Team performer, love to execute process, dependable nine-to-fiver, might need a bit 
more hand-holding and likes processes ready-made so that they can go execute on them 
 
Just as important as performance is the cultural fit. These are skills that cannot be trained (or would require 
way too much of your time).  
 
Some questions to ask yourself regarding cultural fit when meeting with candidates:  
● Do they work hard? Do they have a track record of working hard? 
● Are they able to identify and solve a problem rather than just pointing them out to their manager? 
● Do they take notes? This is a great indication of candidates who are trainable and have the ability 
to execute a process. 
● Do they clean up after themselves? This often is a great indication of team player. 
● Do they ask questions? Do they seem genuinely curious about your business?  
● Do they have experience that relates to your product? 
● Can they communicate with you? When you walk to get a cup of coffee with them, do they start 
the conversation or do you have to drive the communication? 
● Do they display high intellect, and do they seem to enjoy using it to solve problems? 
 
   
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5.1 How to Recruit 
Develop four to seven criteria (e.g., empathy, curiosity, sales skills, diligence) that your hiring team will 
gauge all candidates on, and make sure that the entire hiring team understands exactly what is meant with 
each criterion. Schedule a time for the hiring team to meet after every interview loop to discuss the 
candidate, but only after you’ve asked everyone to submit their feedback using an online form, as this 
avoids groupthink. Even if it’s a clear ‘yes’ or ‘no’ from everyone, still meet and talk about ​WHY​: This may 
lead to some interesting learnings, as sometimes small items will emerge as trends across all of the 
interviews, and perhaps even adjusting your criteria or process for how you interview.  
 
Table 5.1​ Methods of recruiting for each role 
  START UP  SCALE UP  GROW UP 
METHODS OF 
RECRUITING
 
● Word of mouth 
● Personally recruiting 
people in your own 
network 
● Dedicated recruiting 
firm that knows your 
culture 
● In-house recruiter + 
candidates via 
recruiting firm 
 
During a period of active hiring, you may want to consider setting aside an entire day for nothing but 
recruiting. Recruiting is very disruptive to the company flow. The most common example? It will occupy a 
lot of your conference rooms! 
 
Here’s how this would work: 
● Block conference room(s) for the whole day. Make sure they are clean ahead of time (clean the 
whiteboard, etc.). This is best done on a Thursday (you’ll see why below). 
● Notify your front desk/EA/shared space lobby that you will have several candidate guests, and 
provide their names.  
● Set 30 minute interviews each, with 30 minutes of overflow at the end in case it runs long. Those 
who are identified as rock stars should meet with the CEO/VP immediately after their interviews. 
● CEO/VP should block the whole day for “email” so they can interview potentials right away. 
● Offers for each job requisition should be pre-approved internally, so that you just need to add the 
candidate’s name to it. 
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● Candidates who make it past the CEO interview are asked to perform a role-play/task the next day 
(Friday) on-site (or online if they do not live in the area or their travel plans do not permit). For the 
role-play, they can sell their own material, or they can use your standard deck.  
● Have one person on your staff coordinate the candidates and process in a master tracking sheet. 
 
Even during periods when you’re not focused on hiring, you never know when you will run into someone 
who is the perfect fit - perhaps your Uber driver, or the barista serving your coffee. So be sure to have 
‘recruiting business cards’ always on hand you can pass out. You can use your regular business card, or 
think about printing a different version that says “I think you would be a great fit, and we’re hiring!” 
 
   
78 
 
Here are a few great exercises you can ask candidates to perform during an interview. 
 
Table 5.2​ Role-play exercises to use when interviewing candidates for each sales role 
  MDR/SDR  AE  CSM  DIRECTOR 
EXERCISE  - Role-play an 
outbound cold call 
- Write an outbound 
email 
- Chat with me via 
text message as if 
you are in a chat on 
the website 
- Find 10 prospects 
using with LinkedIn 
and talk through 
why they are good 
prospects 
- Role-play the 
opening of a 
conference call 
- Role-play an online 
demonstration 
- Build a pipeline: How 
many deals, 
meetings, and leads 
are needed for you 
to perform 
- Role-play negotiating 
a contract 
- Draft the agenda for 
an onboarding call 
on the whiteboard- Role-play an 
onboarding call 
- Role-play a call with 
a frustrated 
customer 
- Demonstrate how 
you orchestrate 
bringing a new 
customer 
stakeholder up to 
speed 
- Have them create a 
forecast for $10M 
in revenue 
- Role-play how they 
would coach an 
underperforming 
rep  
- Ask specific details 
of how they coach 
the team beyond in 
1-1s and “on the 
floor” 
- Develop a forecast 
using ACV, sales 
cycle, conversion 
rates, and churn  
- Design your sales 
dashboard for the 
leadership/board 
SKILLS TO 
LOOK FOR 
You want to see 
excellent verbal and 
written 
communication skills. 
You are looking for the 
candidate’s ability to 
control the situation. 
You are looking for 
how they interact in 
different mediums, 
their ability to stay 
calm, and control the 
situation with the best 
customer experience 
possible. 
You want to see 
structured thinking, 
positive but firm 
coaching, and ability 
to motivate in 
negative situations. 
 
 
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Best Practices 
 
Recruiting is not just done by you...involve others, even if they are not obvious. For example, inform the 
front desk manager, regardless of whether they work for your company or for your shared office space. 
Ask the front desk for their feedback on how the candidate interacted with them (were they friendly, 
dismissive, etc.). And never, never hire a candidate who is disrespectful or dismissive to anyone on the 
team - regardless of role or seniority. That is a culture cancer that can easily be avoided. 
 
Just don’t listen to what candidates say, but observe their behavior. Here are a few common ways of 
identifying behavioral traits that we have found to be extremely important: 
● Do they take notes? For instance, in the first interview, the interviewer can state the five key things 
you are looking for in this role. An hour later, have another interviewer ask the candidate to repeat 
those five things. If the candidate doesn’t remember what they were, do you think they will 
remember to take notes of the key criteria on a customer call? 
● Do they clean up after themselves? Offer water to a candidate. Upon leaving the room, notice if 
they clean up after themselves. Many team cultures are based on the idea that “everyone does the 
dishes”, so figure out if the candidate would blend in with that environment. 
● Are they honest and sincere? Throughout the conversation, gauge the person’s level of interest. Do 
they seem truly curious and genuinely interested in your company and this role? Are they asking 
you questions that are thoughtful and applicable?  
 
None of these by themselves should be a disqualification, but as a whole, it should provide a story. 
 
Common Questions 
 
Q: Should I use a recruiter? 
A: Early on, you should hire people you know.​ However, once you enter “Scale Up” mode, we 
strongly recommend that you adjust your strategy.  
 
   
80 
 
Table 5.3​ Recruiting strategies, by phase 
UP TO 10 EMPLOYEES  11-25 EMPLOYEES  25+ EMPLOYEES 
Do your own recruiting via your 
network of trusted people. 
Seek out people on LinkedIn and 
write personal notes from the 
Founder/CEO to ask them for a 
coffee. 
25-49 people:  
Develop a relationship with a 
trusted recruiter who knows your 
culture. They should help with 
open positions, but also keep an 
eye out for great candidates and 
always send them your way.  
50+ people:  
Consider an in-house recruiter. 
 
Q: What is the best way to use an external recruiter? 
A: Invite them over to your company. ​Explain the culture to them and who you are looking for. Ask for 
their help, what is possible, what compensation levels they recommend, etc. A good recruiter can provide 
you with job description, pay analysis, titles, and more. But always remember that recruiters (especially 
sales recruiters) are primarily sources for candidates. They can not interview your candidates and do not 
typically provide much more depth than finding the right “type” of candidate, usually based on a resume 
screen. 
 
Q: Should I pay the recruiter a retainer? 
A: Only for executive positions, and only once you have reached at least ~25 employees. ​If less 
than that, you should still be searching through your own network and through VCs. 
 
Common Pitfalls 
 
Pitfall 1: Hiring people only when you need them. ​You may say “no” to a great person because you 
think you don’t need them yet. In rapid growth mode, we can always make great people work. Are they 
open to a more flexible role until everything sets in? If yes, then make the hire.  
 
Pitfall 2: Your recruiting process is built around candidates.​ While in Scale Up mode, you may find 
you are interviewing a lot of people, and you do it per their availability. This is causing massive disruption to 
your company because you are unable to find deep focus time to get work done. Instead, organize a 
recruiting day per week/month. Then properly prepare the organization, block a meeting room for the 
81 
 
entire day, and clean up the office to make a good impression. If needed, hire someone for the day to 
manage the front desk. A few key tips: 
 
● Inform your recruiter and ask for their help to fill the calendar. They will be interested, as this makes 
for a very efficient way for them to find quality candidates for you. 
● Recruiter performs initial screening calls with the candidates. The hiring manager performs 30 
minute interviews on a Thursday, with 15 minute overflow + 15 minute reset. If a candidate 
appears qualified, they are walked into the CEO/founder’s office for a 15 minute chat. Qualified 
candidates are asked to come in the next day/online for a 60 minute group interview by the 
executive team.  
● An offer is made by Friday afternoon after you’ve done a back-channel check with a trusted person 
using shared contacts. 
 
 
 
 
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Figure 5.1  
Sample calendar of 
a recruiting process 
for a company 
during Scale Up 
mode 
 
   
83 
 
5.2 How to Onboard New Employees 
 
You’ve managed to get through the tough part of finding great employees. But stay on point! These 
employees need guidance and training before they can start producing. You probably don’t have the time 
to run a full onboarding program every time you bring on a new hire group, but there are ways that you 
can make it easy on yourself. And yes, you must have some kind of onboarding program. Don’t just put 
new reps on the phone their first day! They’re not ready! 
 
A few guiding principles here to get you started: 
● Onboarding isn’t just the first week or two. It’s just a reality that humans can only handle so much 
new information at once. Reinforce over time, with different methods (classroom, hands-on, etc.). 
● Onboarding and training new team members should be the responsibility of the entire company. 
Be sure that your existing team knows that training new hires is a worthy investment of their time 
and energy. The better prepared they are, the better and faster they can start contributing. 
● It’s crucial that new reps hear about the company strategy directly from you and the rest of the 
leadership. This sets the tone, clarifies where the company is headed and why. That’s a message 
that should be delivered directly from the source, not passed down in a game of telephone. 
● A common mistake in onboarding sales reps is not making them get close to the product, 
especially if you have a technical product. Don’t let this happen to you! A portion of their training 
should include working with customer support. Some companies even have a requirement for 
every employee to spend a few full days per year doing customer support.  
● Create a buddy system: Every new hire should be paired with an existing employee who they can 
shadow, and who can show them the ropes.  
● Your onboarding program should get better every time you run it. Get feedback from your existing 
team AND the new hires on how the program went - both immediately after, as well as a few 
months after once they have settledinto their spot. They will have some great perspective at that 
point on how to improve the program.  
 
Here’s a sample onboarding program that you might use for your first few reps that you bring on to the 
team.   
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Table 5.4​ A four-week enablement plan for a startup (e.g. the first rep) 
WEEK 1 (DETAILED PLAN)  WEEKS 2, 3, 4 (GENERAL GOALS) 
● Day 1 AM: Welcome from the CEO/founder. 
Intros and icebreakers. Discuss the vision and 
goals of the company. Team/welcome lunch. 
● Day 1 PM: Set up IT/laptop/desks. Go over the 
top deals that were won, talk through why each 
customer purchased.  
● Day 2 AM: In-depth product demo by the 
founder. Record it! Understand the ‘why’ behind 
how it’s done. 
● Day 2 PM: Pipeline conversation with the key 
members of the team. Talk through goals, and 
the path to get there. 
● Day 3 AM/PM: Visit a few customers together 
with the CEO/founder. Take close note of how 
your service is positioned. Debrief at the end of 
the day. 
● Day 4 AM: Establish a simplified sales process 
(use this guide) and get a list of content (content 
map) that the CEO/founder is using to educate 
and wow customers. 
● Day 4 PM: Present and role-play with the 
founder until you get it right. 
● Day 5 AM: Role-play again with the founder. 
● Day 5 PM: Draft a 30/60/90 day plan. 
Week 2: 
● Attend an online event/webinar/conference. 
Become familiar with the industry.   
● Learn three customer use cases by heart. 
● Practice pitching (record a video of yourself) 
with a friendly audience. Focus on having a 
conversation with them rather than presenting.   
● Sit in on as many customers calls as possible 
● Meet with the person installing/onboarding your 
service, discuss what is working, and what is 
not working 
● Review/get sign-off on 30/60/90 day plan. 
Week 3: 
● Perform three customer calls with the founder 
shadowing; discuss feedback after the call. 
● Start getting on the phones full time: Make 100 
phone calls this week (150 next week). 
Week 4: 
● Two or three day road trip to apply what has 
been learned; this can be an event or 
conference. 
 
Record everything you can! Watching and 
reviewing your work is quickest way to ramp. 
 
 
   
85 
 
As you move into the Grow Up and Scale Up phases, your onboarding needs will be very different than 
when first starting out. See below for a more extensive sample onboarding plan that would be used in 
these later stages of growth. With a variety of speakers and modes of learning, the entire company is 
helping to train new hires.  
 
Table 5.5​ A four-week enablement plan for onboarding new reps in Grow Up and Scale Up 
WEEK 1 (DETAILED PLAN)  WEEKS 2, 3, 4 (GENERAL GOALS) 
● Day 1 AM: Welcome from the CEO/founder. 
Intros and icebreakers. Tour of the office. 
● Day 1 PM: Set up IT/laptop/logins/tech/ 
badges/desks. Take care of HR paperwork.  
● Day 2 AM: Company vision/strategy. In-depth 
product demo. 
● Day 2 PM: Presentations from the rest of your 
executive team, covering their vision, overview 
of their team, and how they work with Sales. 
● Day 3 AM: Team with engineering/customer 
support to answer customer support inquiries. 
(amazing way to quickly learn the product and 
understand the voice of the customer!) 
● Day 3 PM: Start shadowing their buddies. They 
should watch their buddies using CRM, listen in 
on calls, shadow everything they are doing. 
● Day 4 AM: Sales process overview. Training on 
how to use CRM and include basic training plus 
overview of customization. 
● Day 4 PM: Practice asking questions to identify 
customer pains in small groups. 
● Day 5 AM: Continue buddy shadowing.  
● Day 5 PM: Diagnosis practice: Each new hire 
runs through how they would diagnose a 
customer’s pain. 
Week 2: 
● Start to master the pitch, and get coaching from 
senior sales reps.  
● Know the basics of using CRM. 
● Mastery of the industry: Self-study using 
resources to get up to speed on industry 
trends. 
● In-depth presentation from Marketing team. 
Understand sources of lead flow, types of leads, 
marketing events, programs and partners. 
Week 3: 
● CRM mastery 
● Review quota, compensation and territories 
● Heavy on call shadowing 
● Role-play customer calls with different scenarios 
and use cases  
● Pass your pitch certification by presenting to 
sales managers 
Week 4: 
● Start getting on the phones if certified 
● Create territory plans 
● Evaluate their readiness; determine if any 
knowledge gaps still need to be filled 
 
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5.5 Training Specific Skills 
Regardless of role or skill level, keep in mind that there are a few core principles that EVERYONE on the 
team should be doing: 
 
Table 5.6​ Customer-centric selling principles 
#1 Pain  
NOT Fit 
#2 Emotional 
BEFORE Rational 
#3 Educate  
DO NOT Pitch 
#4 Assist Buying  
DO NOT sell 
#5 Value  
in every interaction 
Do your research 
and only reach out 
to those who have 
a ​pain​, not to 
those who are a ​fit​! 
Emotional impact 
benefits people, 
rational impact 
benefits corporations. 
Focus first on the 
emotional impact.   
 
Trust that if you 
educate the 
customer that they 
will make the best 
decision.  
People hate being 
sold, but they love to 
buy. Stop the selling; 
instead assist people 
who want to buy. 
Don’t just do 
check-ins. Instead 
provide value in 
every interaction with 
every customer, 
every time.   
 
Building on those principles, there are certain core skills that each person in each role must have. See 
below for a breakdown of these basics. And as a reminder, this diagram shows how each role comes into 
play in the early phases of growth. 
 
Figure 5.2​ The key sales roles across the sales cycle 
 
   
87 
 
Table 5.7​ Core skills to master at each sales role. For each of the core skills labeled as Moments, see Chapter 7. 
The Sales Director role should be able to perform all of the skills, but should focus only on the ones indicated. 
CORE SKILLS  MDR  SDR  AE  CSM  DIRECTOR 
Communication ​(Moment 1)  x  x  x  x  x 
Prospecting​ (Moment 2)  x  x  x     
Conducting discovery ​(Moment 3)  x  x  x  x  x 
Diagnosing the issue ​(Moment 3)    x  x  x   
Establishing a critical event    x  x    x 
Assisting the decision process      x  x  x 
Recommend - Conducting a demo      x     
Overcoming objections      x  x  x 
Trade ​(Moment 4)      x    x 
Commit/Close      x  x  x 
Onboard/Orchestrate ​(Moment 5)        x   
Use/Achieve Impact ​(Moment 6)        x   
Upsell/Account management 
(Moment 7)        x  x 
Coaching          x 
88 
 
 
   
89 
 
   
90 
 
 
 
 
 
 
 
 
 
CHAPTER 6  
SALES ENABLEMENT 
 
   
91 
 
A little enablement goes a long way. You can kick start enablement for your team with the following:  
 
1) A content journey of what material to use/when: ​As a founder, you know exactly when to use 
an article, a blog post, or even a tweet. How do you get your team to do the same? 
 
2) A few key hardworking enablement templates:​ These are assets that are dead-simple to use, 
and perfect for completing together as a team and using in coaching exercises. 
a) Qcards 
b) Bingo cards 
c) Sales Playbook, Prospecting Playbook, Customer Playbook 
. 
3) ‘Posterized’ design and best practices for processes:  
a) Sales process 
b) Tool stack 
 
In the early phases of growth, if you and your team spend just a little bit of time and effort to set up a 
process for documenting the knowledge base that you already have and what you collect over time, then 
you will quickly have a robust content library that you can use for ongoing learning and training new reps. 
 
Table 6.1​ Types of enablement needed at each phase 
  START UP  SCALE UP  GROW UP 
Content Journey  Spreadsheet (10 items)  Spreadsheet (20+ items)  Content Map 
Enablement  N/A  QCards 
Sales Playbook (two 
pages) 
Bingo cards 
SaaS Method Playbook 
Design   N/A  Customer Journey   Tool stack 
Sales Process 
 
Content Journey 
As afounder, you are probably quick to draw on a wealth of articles that you’ve read over the years, 
quotes from books, and blog posts you keep as a reference. This helps you as you work with your 
92 
 
customers, so send them this information when you feel the time is right. But as you scale the company, 
this kind of knowledge needs to be archived, updated and shared. The way to do this is by building a 
content map. 
 
 
Figure 6.1​ Example of a content map used for a company in Grow Up phase - work towards this!  
 
   
93 
 
Horizontally across the content map, you see the journey your customer goes through (as will be explained 
in Chapter 8 on Data). Vertically down the map, the customer goes through four stages: 
1) People first do research and understand the problem 
2) Shortly after, they look for and research the solution 
3) They look for a way to see it work in action 
4) Then they take an action: download something, click on trial, or start to chat on the website  
 
As a customer learns, they use the next level of content. Take for example, “Seeing It Work.” The customer 
isn’t interested in committing to a two-hour whiteboard session; they’re just looking for a quick video. But 
the level of commitment increases as they progress through the experience and become more invested.  
 
Table 6.2​ An example of a type of content across the customer lifecycle 
  MARKETING  PROSPECTING  WINNING STAGE  ONBOARDING   USING 
“Seeing It 
Work” 
Youtube video  Online demo by 
an SDR or AE 
Sign up for a trial  Mutual commit to 
a proof of concept 
Demonstrate 
real case 
study 
 
Now, the amount of content that you have created in the Scale Up phase will be much different than the 
amount you have available in the Start Up phase. But at each phase, you can easily keep track of what 
you have and how it should be used. Here’s how:  
  
Table 6.3​ An example of how to start an early-stage content library that everyone on the team can use 
TYPE OF 
CONTENT 
PHASE  WHAT IT’S USED FOR  SPECIFIC POINT 
eBook  Marketing  Shows the customer the types of solutions that are 
available 
Page 3, second 
paragraph 
Trend report  Marketing  Shows the customer what trends they should think 
about applying to their business 
Page 12 
Checklist  Winning  Shows the customer what they need to do in order 
to implement a solution like ours  
3rd item 
94 
 
Enablement Templates 
QCards 
Qcards are a quick reference guide that sellers can keep on their desk and easily reference at any time. 
The format is 5x8 cards, bound by rings, that sellers can flip through to quickly find the information they 
need in order to prepare for discovery calls. They include overviews of buyer personas, dives deep into 
their mindsets and emotional/rational pain points, and frameworks for preparing for discovery (see 
screenshots below). 
   
Figure 6.2​ Sample of QCards describing Customer Profiles to allow sellers to sympathize with their prospects 
 
Bingo cards 
Play bingo with your team! Record each type of customer call, and use these bingo cards to have your 
team listen for each of the elements of the conversation, checking them off as the call progresses. After 
the game, discuss how the call went and how the sales rep performed in using the call frameworks. 
95 
 
 
Figure 6.3​ A sample Bingo Card, used to reinforce the sales process 
   
96 
 
Process chart 
A sales process chart summarizes your sales process: The goal of each stage, the actions you should take 
in each stage, and the criteria for progressing through the process. Following a strict sales process is the 
cornerstone of a successful sales team. 
 
 
Figure 6.4​ An overview of the entire sales process, available as a poster (Mimeo) or template (LucidChart) 
 
97 
 
Sales Playbook 
 
Figure 6.5​ A 1-page Sales Playbook template 
 
   
98 
 
Best Practices 
 
There are a few proven best practices that you can employ in order to quickly build a robust enablement 
program and content library for your team. Putting in just a little bit of time to make this happen will provide 
rewards for your team tenfold.  
 
● Create a library of: 
○ Content for each stage of the sales cycle: Create a spreadsheet with links, by stage, to 
each asset (this should be no more than 20 assets). Set a regular schedule for updating the 
assets, and involve your team in rotating ownership of this. 
○ Successful prospecting emails: Open a shared doc and have your team members paste a 
copy of their best performing prospecting emails. 
● Learn from your wins: With every new win celebration, interview the sales POD on the same set of 
questions for no more than five minutes: Talk about who they worked with (show the customer’s 
LinkedIn profile), how they came to us, what was their critical event, what was the impact, who did 
we compete with, what was the trade-off. 
○ Record the interview and then create a QuickQuiz. New reps should listen to the interview, 
and then fill out the QuickQuiz. The QuickQuiz should contain questions such as:  
■ Look up the person on LinkedIn and find descriptive traits that will help to 
understand this person’s mindset (e.g., “was the first to innovate” within a peer 
review). 
■ Fill in the critical event, impact, etc.  
● Identify your buyer’s process: Have each team member pick out one of their customers that they 
would like more of (i.e., a model of an ideal customer). Each person should do a root search in their 
email on the company domain name (e.g., acme.com…). Look for the first several emails that were 
exchanged, and discuss what trends and insights you can find from that process such as: What 
was the value prop that was discussed? What was the language used?  
● Develop your talk track: Have each rep record a random call. Meet with them individually to review 
the call, and then have the rep present what she did really well and what can be improved for next 
time. Create a training/onboarding module from this that you can use for new hires. 
 
   
99 
 
Commons Questions 
 
Q: Do I need some kind of tool to manage all of this content?  
A: Nope. ​Once you hit serious critical mass with a sales team (global team of 50+), then it may make 
sense to use an enablement tool. But until then, your effort and budget are better spent by keeping it 
simple with some well-organized spreadsheets. 
 
Q: These templates are cool, but I don’t have the time to fill all of these out. 
A: You shouldn’t! ​Do a workshop with your sales team across a few Friday afternoons, two hours each 
Friday, when you get together in a room and each start filling out an asset. Rotate to check each other’s 
work a few times, and before you know it, you will have the beginnings of your enablement content library.  
 
 
Common Pitfalls 
 
Pitfall 1: Letting enablement assets get stale rather than setting aside some time to keep them 
updated. ​In the early phases, it’s not yet necessary to have a dedicated enablement team member. So 
this means that before you hit that point, your sales manager must build enablement into the 
responsibilities for the entire team. They should set up a regular cadence for reviewing templates, updating 
materials, and building in more best practices. Involving team members is key here: Get one rep to spend 
30 minutes helping with this each week. 
 
Pitfall 2: Build enablement into team goals in some way. ​This is an undeniable way to ensure that the 
entire team understands the value of enablement and takes ownership of it. There are lots of ways to do 
this: Make it a part of their overall compensation, provide spot bonuses for great contributions to the 
content library; feel free to get creative with it. 
 
   
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101 
 
   
102 
 
 
 
 
 
 
 
 
 
CHAPTER 7  
THE SAAS METHODOLOGY 
 
 
 
   
103 
 
The goals of the blueprints we provide are simple: Create a framework, not a script. Each blueprint will 
show how to perform a set of actionsduring a Moment That Matters. Each of these frameworks can be 
improved as your process is refined until they work at their absolute best. But before we share some of 
these blueprints, we want to provide a guideline that we have found to be critical in today’s sales culture.   
 
Your interest in helping a customer resolve their problem must be authentic. ​It cannot be 
manufactured, and you should not use authenticity as a “trick” to close a deal. More and more marketing 
organizations are making authenticity a concept: they recommend to use of certain words, record videos 
on your LinkedIn, etc. We do not believe this is sustainable. If you master the five principles below, you will 
be genuinely authentic - not because it helps you close a deal, but because during the process of 
executing these principles, you have become someone who cares.  
 
Principle 1.  Understand their pain  
Do your research and only reach out to those who have a pain or whom you think you 
can help avoid it. Do not reach out to people who are “just a fit!” 
Principle 2.  First emotional, ​then​ rational  
Humans make decisions emotionally, and then justify rationally. Focus first on the 
emotional impact. 
Principle 3.  Educate through storytelling; do not pitch  
Trust that if you educate the customer, they will make the best decision. Therefore, help 
your customer think through the problem they are experiencing, and share best 
practices of others who experienced the same. 
Principle 4.  Assist the buying process  
People hate being sold, but they love to buy.  
Principle 5. Provide value in every interaction  
Don’t just do check-ins; provide value in every interaction with every client, every time. 
Offer market information, insights, use-cases and whatever else you can to add value. 
 
 
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We have identified the Moments That Matter, and aligned them along the impact journey of your customer. 
Next, we are connecting each moment to a corresponding conversion metric (for more about these 
metrics, see Chapter 8). We can now provide a series of examples of specific actions your 
customer-facing teams can take during these moments to improve the respective conversion rates at each 
moment. And as you will learn in Chapter 8, a small improvement in conversion rates at these moments 
can have a big impact on revenue. 
 
 
 
Figure 7.1 ​Key Moments That Matter, the impact journey, and the corresponding conversion metrics. 
 
   
105 
 
The seven key moments we are going to focus on are: 
 
1. Reach out ​based on a pain they may have, be relevant to them from the first moment 
2. Have a conversation ​as a human being, not a sales qualifier 
3. Perform a diagnosis ​on the customer’s situation before you prescribe a solution  
4. Trade, not negotiate:​ maintain value for your product by trading items of equal value 
5. Orchestrate, not onboard:​ redo the deal once the customer is signed 
6. Achieve impact, not pursue usage:​ look for both the emotional and rational impacts 
7. Grow in different areas:​ Renew, up-sell, re-sell, and cross-Sell 
 
Moment #1: ​Reach out to customers who have pain 
 
When we ask our customers who their prospects are, they often mention a job title in a vertical market, 
such as the CTO at a financial institution. Many companies buy, and/or create a list of prospects that hold 
a specific title, in a particular vertical market, and are in a certain region with a specific size. They then 
enrich the database with email addresses, telephone numbers and social handles. This will only lead to an 
ineffective outreach email like the one in the next example.  
 
Dear ​<First Name>​, 
 
I noticed on LinkedIn that you are the {{ ​job title ​}} at {{ ​company name ​}}. The reason I am reaching out 
to you is that others in your industry such as {{ ​first name ​}} at {{ ​company name ​}} ran into {{ ​problem ​}}. 
 
Attached a {{ ​use-case ​}} that describes how {{ ​our company name ​}} helped him/her solve this by  
{{ ​doing this ​}} and how it {{​ caused xx% increase ​}}.  
 
Can we meet for 15 minutes to discuss how we can help you? 
<Close> 
 
Figure 7.2 ​A personalized yet INEFFECTIVE outreach email. 
 
 
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The thing about this email, which is quite representative of today’s sales organizations, is that it is the 
result of correlation, rather than a trigger event.causation. 
 
When we ask the CTO why they signed up for our service, we learn that it was because earlier in the year 
they suffered a security breach. The fact that they were a bank was pure coincidence and thus correlated 
with their profile, but not caused by it. What that means is that for this seller, any other institution that had 
a breach should be a prospect, regardless of it being a bank!  
 
This allows us to rewrite the outbound email based on a trigger event - referencing the customer’s true 
pain point - instead of just based on correlation. 
 
Dear ​{{ First Name }}​, 
 
In your recent article you mentioned that your infrastructure was breached.  
 
Please find attached a use-case from two weeks ago. On page two, I highlighted how the headaches of 
a similar breach can be avoided based on a best practice discovered by {{ ​first name ​}} at {{ ​company ​}}. 
 
{{ ​First name ​}}, let me know if you like to talk to one of our experts on this? 
 
<Close> 
Figure 7.3 ​A personalized, EFFECTIVE outreach email that is based on a customer’s pain. 
 
 
Reaching out to a prospect using a provocative statement takes some preparation. Here are the steps you 
can use to define the provocative statement for each prospect:  
 
Step 1.  Pick one of your own accounts and perform research 
Step 2.  Pick a value prop and use-case that applies most to the customer (the person, not the 
company) 
Step 3.  Research the current situation through online search as well as phone calls to employees 
Step 4.  Outline specifics of the new situation without overtly mentioning your products or terms 
unique to you 
107 
 
Step 5.  Identify a critical date such as a product launch, or an event such as “reaching 1M users” 
Step 6.  Establish rational and emotional impact based on a selected value prop; ensure you have 
a use-case (proof) of a relevant customer (size, location, market, etc.) 
 
Figure 7.4 ​Blueprint of a provocative statement 
 
The caveat here is that we all receive dozens of emails a day that provide no value. Even the cold 
outbound email we described in the example above may soon be a thing of the past if they become too 
templatized and no longer relevant. Low email open rates are already taking their toll on outbound 
campaigns worldwide, and that is even ​if​ those campaigns are well written and based on a prospect’s true 
pain, as we recommend. 
 
Moment #2: ​Conversation, not qualification 
 
One of the first things all salespeople are taught is qualification. This is the task of determining if a person 
representing a company with characteristics - such as size, market, and intent to purchase - qualifies them 
to continue in the sales process.   
 
When sales professionals were selling IBM Mainframe computers, this made a lot of sense. There were 
only a few mainframes to go around, and everyone wanted them. However, the cost of selling entailed 
tens of thousands of dollars with access to specialized resources, such as engineers and architects, that 
provided their expertise around integration into the customer’s infrastructure. Sales had to use a defined 
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set of questions to extract concessions from a customer and based on the answers, determine if this was 
a priority for the seller. In today’s world, a SaaS solution can be integrated into a cloud platform with a 
single click or the provision of a login via an email. Outdated qualification methods designed around 
multi-million dollar products do not apply to high velocity sales. The customer has lots of options, and 
budget is not generally a problem. 
 
 
Figure 7.5 ​How to apply TALKER conversationtechniques to initial customer calls 
 
 
   
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So instead of qualification, we recommend building conversational skills to establish the priority and the 
impact the customer is looking to achieve. The framework for teaching conversation skills is built on an 
easy to remember acronym, TALKER: 
Step 1. T​one of voice, not just in the use of an actual voice, but the use of emoticons in chat 
and email. One of the key elements of tone is speed - for example, not being too fast in 
person, but responding very fast in chat. 
Step 2. A​sk questions. Master not only closed- and open-ended questions, but also learn to ask 
diagnostic questions like a doctor would.  
Step 3. L​isten actively to patterns in the customer’s words, tone, and even their emotional state. 
Learn how to recognize emotional words. 
Step 4. K​eep accurate but brief notes, differentiating situation, pain, and impact while identifying 
causality. 
Step 5. E​mpathize with your customer, consider a relevant use-case story of another customer 
who experienced the same challenges, and share how they resolved it. 
Step 6. R​epeat what you’ve heard to ensure you understand what is being said. 
 
A conversation connects a sales professional with the customer to uncover their real, pressing problem. It 
is the moment in which a hypothesis about customer impact can be fleshed out by a trained professional. 
As you can see in the next blueprint, we can apply TALKER to all kind of moments to start a conversation.  
 
Coming out of this moment, you should have a very clear idea of whether and how your product can 
impact the customer’s business. More importantly, you should have managed the conversation in a way 
that the customer themselves have verbalized the problem and envisioned a potential solution. 
110 
 
 
Figure 7.6 ​Example of a live chat with a customer who came to your website to learn more 
 
Moment #3: Discovery/Demo ​Diagnose before prescribing your solution 
 
As the saying goes: prescription before diagnosis is malpractice. To use a medical analogy, when a patient 
is complaining of symptoms, a doctor must diagnose the issue before prescribing a course of action. In 
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sales, if the salesperson were to immediately start pitching, that would be prescribing the solution before 
fully knowing about the customer’s true pain. 
 
The salesperson’s role is to further diagnose the root cause. This is still not the time for a hard sell (it never 
is, by the way). Instead, the more a salesperson can do to understand the customer’s pain and the 
potential business impact, the better they will be able to accurately recommend an impactful solution for 
that customer. 
 
 
 
Figure 7.7​ How to have a conversation 
   
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EXPERT ADVICE  
Close-ended questions are powerful for setting context for open-ended diagnostic 
questions. But too many in a row, or asking close-ended after a customer has shared a 
pain or desired outcome can drop engagement that results in a mediocre conversation. A 
great sales professional guides the conversation based on what their customer is looking 
to accomplish, not just on the features or benefits they are comfortable talking about. This 
approach will decrease sales cycles and increase the value of deals simultaneously. 
 
DAN SMITH 
Partner, Winning by Design 
 
Questions are the only way to uncover your customers goals and objectives. To diagnose efficiently, use a 
question-based framework that will work in every professional situation, from the emergency room to your 
favorite car mechanic. 
 
Step 1. First ask two or three questions to learn the context surrounding the issue 
Step 2. Then ask questions to understand the pain 
Step 3. Summarize: “So you have [this situation] and [that situation] causing you [this pain]?” 
Step 4. Empathize “I hear this a lot,” or “You are not alone in this.” 
Step 5. Identify both the emotional and rational impact 
Step 6. Establish a critical event 
 
DIAGNOSE THROUGH DEMONSTRATION 
 
In a high velocity sale, you might find a prospect who really wants a quick demo. This does not mean that 
you should jump straight into a pitch. It means that you need to integrate your diagnosis into the 
demonstration: you must ensure your demo is relevant for the prospect, and give yourself an opportunity 
to obtain valuable information, such as the impact your product can have on a their business. 
 
Sales reps will often turn what should be a quick demo into a monologue that lasts 30 minutes. It shouldn’t 
be a surprise that customers lose interest when this happens; there is too much information coming at 
them that they cannot relate to. At the same time, you miss the opportunity to learn about their challenges 
and how you could help them. Here is a visualization of customer engagement during this experience:  
113 
 
 
Figure 7.8​ ​How to diagnose while performing a demonstration 
 
Step 1. Write an agenda of the points you are going to demo in the context of the top priority 
challenges your customer is looking to solve. Keep it to three points on a 30 minute call, 
and five points on a 60 minute call 
Step 2. For each demo point, summarize your previous diagnosis and point out why you are 
showing a particular page, dashboard or feature of your product 
Step 3. Orient the customer with the layout of your product on the screen to show them where 
they should be looking to help minimize distraction or confusion. 
Step 4. Then demonstrate: 
● In the customer’s context, how your product solves their problem 
● “Hand over” controls by asking if there is anything they would like to see 
● Identify impact for each point by asking the following three questions: 
“Would this address the issue you described earlier?” 
“Can you see yourself using this product?” 
“How would this impact your business?” 
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Step 5. At the end of each, summarize the key findings, ask if there are any questions and move 
to the next point 
Step 6. Following the demonstration recap the findings across all three points using the customer 
vernacular 
 
Moment #4: Close ​Trade, not negotiate 
 
This single change in wording has one of the greatest effects on cumulative sales. When salespeople 
negotiate, they tend to think in terms of compromise, specifically with numbers and percentages moving 
up and down. In a high velocity sale, we notice that they tend of offer discounts quickly and in large 
increments. As a result, they often give away discounts far more than they should for little in return. 
 
A company with an innovative SaaS product with an annual contract value (ACV) of $12,000 should 
increase its price annually by at least 10% given its rapid product development. By giving a 20% discount 
during negotiation, an inexperienced negotiator may view this as “only $2,400”, however this adds up over 
three years to be $10,920, or nearly one year of revenue.   
 
And for what? Most deals that reach the negotiation stage seldom turn on price.​ ​Instead, we encourage 
organizations to think of negotiation as ​trading​, and of discounts as ​price adjustments,​ and make these 
price adjustments small. In trading, both parties give up something of value in order to be better off. By 
definition, trading is a win-win situation. What do they trade for? There are any number of things a 
customer can do or say that will significantly help a business. References, case studies, social media 
mentions, PR quotes and all kinds of other items can form a menu of trading options at different levels of 
price adjustment. 
 
This puts a price on discounts, and everyone knows what happens when we pay attention to the price of 
something: its value becomes clear. So, when a customer isn’t willing to do a PR mention and turns down 
the discount, the average discount rate for the team goes down. This single change has caused the 
average discount rate to move from more than 20% to less than 10%. That is revenue that goes straight to 
the bottom line.115 
 
 
Figure 7.9​ How to trade throughout the customer conversation  
 
Step 1.  Know the person on the other side of the table, their way of responding, etc. 
Step 2.  Understand the situation: what is the impact, and the critical event?   
Step 3. Prepare a list of trade items, and understand value of each 
Step 4. Do you understand all the elements of the offer?  
Step 5.  Get all negotiation items on the table: price, terms, setup fee, etc. 
Step 6.  Repeat/Ask what you heard, ​“So if I got it right, you want ___ . Is there anything else?” 
Step 7. Prioritize the issues: Let me ask, what is most important to you: Price or...   
Step 8. Before you make the offer, make sure you are talking to the decision maker  
“If we come to an agreement can you make the decision by {today}.”  
Step 9. Make the offer, do not hesitate; be clear and be concise 
Step 10. Listen and repeat the counter-offer 
 
 
   
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Moment #5: Kick-Off ​Orchestration, not onboarding 
 
Onboarding is a term that has become so overused that it’s lost its meaning. Everyone thinks they know 
what it means, which usually comes down to something like “getting the customer set up with the 
product.” While the technical setup may be the immediate concern, it doesn’t cover the larger missed 
opportunity that this first customer interaction after commitment represents. 
 
You must understand that the relationship before the commitment and after the commitment has 
undergone a fundamental change:  
 
● Before the contract:​ The buyer did not want to provide too much insight into their business for 
fear of losing leverage, and perhaps the seller may not have been completely transparent on how 
things really work.  
● After the contract is signed:​ The buyer is willing to provide a lot more insight into how their 
business works to ensure success. This may even involve an adjusted timeline, additional budget 
available, and access to previously inaccessible executives.  
 
This window of mutual exposure is only open for a short while. So instead of just ​onboarding ​the customer 
into the product, this should be treated as an opportunity to ​orchestrate ​the entire business relationship 
from that point forward.  
 
It is during onboarding, while the customer is vested in a successful outcome, that the seller (in this case 
the CSM) has the opportunity to set expectations for how the product will impact the customer, how it is 
measured in milestones of success, and ultimately set up the relationship so it has a real impact on the 
customer’s business. It becomes a strategic business discussion rather than just a technical one. Just 
keep in mind that you might need to treat this as two different discussions: the more strategic one which is 
business focused, and the technical one which is more tactical.  
 
117 
 
 
Figure 7.10​ The importance of orchestrating rather than just onboarding 
 
Step 1.  Handoff the deal​ to the CSM/Onboarder using Impact and Critical Event details  
● The sales rep should stay involved to ensure continuity 
● Time is of the essence: provide short frequent communication with updates 
Step 2. Redo the deal. ​Since the relationship has changed, the salesperson revisits all the 
details with the buyer, identifies key stakeholders and orchestrates building the 
relationship.   
● Consider creating a 3x3: Three stakeholders on your team, each who work with 
three stakeholders on their team  
● Then have people from your team reach out to people on their team  
● May involve sales ghostwriting the first message 
Step 3. Kick-off 
● Send a welcome note, a brief note, may include an icebreaker such as t-shirts  
● Create the impact journey of when a specific impact is achieved 
● Obtain the date when the customer has their ​monthly internal executive meetings 
118 
 
● Establish cadence of ​scheduled events​ such as the renewal and its conditions  
● Set alerts for​ triggered events​ such as opportunities and/or risks, and define the 
actions you will take on each alert  
 
Moment #6: Renew ​Ensure impact, not usage 
 
Many customer success software platforms track product usage. Whether measured in percentage of 
seats used, or number of logins per time period, or number of features used, product usage is often the 
proxy for success. But this is measuring not customer success, but rather the product’s success. 
 
 
Figure 7.11​ The importance of frequent impact reports vs. a Quarterly Business Review 
 
A more customer-centric approach would be to explore whether the customer is getting the results​ ​they 
need out of the product. After all, from a customer’s standpoint, what could be better than solving their 
pain with the minimum amount of usage possible? 
119 
 
 
It’s often the case that more usage will solve the problem, in which case usage is a reasonable proxy for 
impact. But be sure to keep CSMs focused on the fact that the customer is buying impact, not usage. 
 
Step 1. Orchestrate a road to achieve desired impact  
Step 2. Practice how to handle frustration when an issue occurs 
● Communicate: Establish a solid way of communicating, e.g., “TALKER” 
● Disarm: Express empathy/disarm the situation without taking on blame 
● Research: Important to find relevant materials! Do not diagnose without it! 
● Diagnose: Perform a proper diagnosis based on the research 
● Proof: Before you prescribe, accumulate proof of your case 
● Prescribe: Recommend based on research/diagnosis/proof 
● Communicate: Summarize, and offer help to implement 
Step 3. Provide a​ scheduled report ​every month that clearly indicates the impact achieve 
● Report must have an easy to understand chart, visualizing the impact 
● Achieved emotional and rational impact should be presented 
● Present benchmark of the impact of the customer compared to others in the 
industry 
● Specify risks and opportunities in the impact report 
● Always look forward 6-12 months regardless of the expiration date 
Step 4. Renew/expand the contract well before the actual renewal due date; the renewal should 
be based on the emotional and rational impact for the customer, not just the usage 
 
 
 
EXPERT ADVICE  
Treating customer success as an afterthought isn't just damaging to your company brand 
- it's detrimental to your growth. We know that as much as 75% of SaaS revenue comes 
after the customer commits to your product. Why risk future introductions, relationships, 
branding opportunities, and revenue stream by providing a poor or non-existent customer 
experience? Invest in a Customer Impact Journey early - from the sales handoff to 
onboarding to realizing impact and beyond.  
 
EMILIA D’ANZICA 
Sales Architect, Winning by Design 
 
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Moment #7: Upsell ​Grow, rather than sell more 
 
“Land and Expand” has become a buzzword in SaaS marketing circles. It’s a useful metaphor, but it’s also 
a metaphor rooted in conflict. It sees the customer as a territory to be mapped, flanked and conquered. It 
is reasonable to assume that is not how the customer views the relationship. Instead, you should think 
about growing the relationship and growing the customer’s business. This can only be achieved by having 
an impact. Whether that impact is lower cost, higher revenue, or an improved customer experience, it is 
the impact that matters to the customer - and the more impact delivered, the more the customer will want 
to use (and buy!) the product.  
 
Figure 7.12​ Four growth areas, each with its own opportunity 
 
Growth is a function of providing great impact to stakeholders inside an account. If a new stakeholder 
needs to be convinced for the first time of the impact you deliver, this is referred to as a new business win, 
and should be the responsibility of an acquisition-focused sales rep (AE). 
 
When an existing customer renews the contract with no new stakeholders or impacts, it is referred to as a 
renewal. Often these renewals occur automatically on or right before the anniversaryof the contract. In 
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many cases, the CSM is responsible for this. This is a flawed approach because you ignore the growth 
potential from a customer willing to renew nine months into a contract.  
 
When an existing customer buys more services, such as more seats or additional features, this is 
considered an upsell. CSMs are capable of doing this reactively, but if you want to reach out proactively, 
you are likely going to need an acquisition-focused salesforce. When a new stakeholder in an existing 
account needs to be won over, this is referred to as a cross-sell. This should not be handled by a CSM, as 
this the most complicated sale and you may need to unroot an existing competitor chosen by another 
champion. This is often better handled by a team familiar with competitive scenarios,​ ​such as the 
Acquisitions team. Each of these sale types create growth loops, each with its own specific goal. 
 
 
Figure 7.13​ Growth opportunities mapped back to key moments, creating Growth Loops 
 
Step 1. Create a 2 x 2 matrix with the four growth areas. 
Step 2. Assign each area to the right person in your organization. For example: 
● Renewal of the contract ⇒ Customer Success Manager 
● Upsell to a new product ⇒ Sales or Account Management  
● Resell to a new a new benefactor ⇒ Sales or Account Management 
● Cross-sell to a new benefactor ⇒ Account Management 
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Step 3. Determine the growth conditions in each area. For example, under Renewal when impact 
is achieved, there are still various growth opportunities: 
● Annual x% increase in price 
● Renew earlier, e.g., renew at 9 months into a 12-month contract 
● Extend contract terms from a 12-month to a 24-month contract 
Step 4. Create a blueprint for each of these growth areas, addressing the most common 
scenarios. 
Step 5. Practice performing these actions with the team! Do not do this with a customer without 
having first practiced and role-played out the most common scenarios. 
 
Bonus Moment: ​Staging of Meetings 
 
Most business today is the result of a series of meetings. The quality of each meeting determines how 
many meetings you need. We’ve found that successful salespeople have fewer and shorter meetings. 
 
 
Figure 7.14​ How to stage meetings to achieve the goal and shorten the sales cycle 
 
   
123 
 
By reviewing tens of thousands of sales meetings, both in person and on the phone, we’ve found that 
great meetings follow a consistent blueprint: 
 
Step 1. ACE ​the meeting. Check the end time and set the end goal of the meeting: 
● A​ppreciate: ​Appreciate you taking the time to meet today. 
● C​heck time:  Are we still good until 11am?  
● E​nd goal: The End Goal of this introductory call to see if we can help you. If so, 
we normally move forward with a demonstration. Does that sound good? 
Step 2. Present an agenda to ​meet the end goal​ and ask the customers to contribute:   
● What else would you like to discuss today? 
Step 3. At the end of the meeting, ask if the goals were met: 
● May I ask, based on what we discussed today, do you think we can help you? 
Step 4. Confirm that the client is ready to move forward: 
● Are you ready to move forward with a demonstration? 
 
Next is a critical part where we link to the outcome of the next meeting. 
 
Step 5. Set the stage for the next meeting: 
● Have you done a demonstration like this before? 
● What has been the outcome of a successful demo in the past? 
Step 6.  There are three ways to get the right people in the room to achieve the end goal. 
Ask with an open-ended question:  
● Is there anyone else who can benefit from attending this demonstration? 
Ask with a closed-ended question:  
● Mary is your head of Sales Ops, right? Do you think she can benefit from attending 
the demonstration? 
Ask with a third party reference:  
● I recently did a demo with {{first name}}, she is one of your peers and decided to 
bring in her head of Sales Ops to address the integration with your CRM. I notice 
Mary is your head of Sales Ops. Do you think she can benefit from joining us? 
Regardless of the outcome, you can always follow through: 
● Since Mary can’t join us, what does she normally care about? 
 
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RECAP ​Blueprints 
 
To impact change, we recommend the following steps: 
 
Step 1. Identify the key moments for your business 
Step 2. Measure the conversion metrics and maintain a trendline over time 
Step 3.  Determine the actions performed during the key moments, and visualize them in a blueprint 
Step 4.  Brainstorm how each key moment can be improved 
Step 5.  Iterate in 15- to 30-day intervals until you have improved each metric by 10% 
Step 6.  Benchmark your performance against others relevant to your business 
 
 
 
 
 
 
 
 
 
 
 
 
   
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CHAPTER 8  
DATA-DRIVEN 
ORGANIZATION 
 
 
   
127 
 
With so many tools and ways to capture data, it’s very easy to get overwhelmed with this data explosion 
and become lost when trying to boil it down into meaningful insights. It results in either no action, or taking 
the incorrect action that could have an adverse impact. Since most decisions in sales today are guided by 
data, we have to establish the data model. Let’s start by standardizing what we are going to measure. 
 
 
Figure 8.1​ ​End-to-end sales methodology with customer-centric measurement points  
 
 
 
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Key SaaS Metrics and Definitions 
There are three types of metrics that contribute to the standard data model: 
 
1. VOLUME METRICS​: ​Tracks the volume of leads, opportunities, deals and revenue 
 
SUSPECT A person who may be interested  
PROSPECT  A person who fits the profile 
MQL  [Marketing Qualified Lead] A person who expresses interest by visiting your website, for example 
SQL [Sales Qualified Lead] A person who has a pain and wants to take action to impact the situation 
SAL  [Sales Accepted Lead] Verified by a sales pro that an impact can be achieved within allotted time 
COMMIT  Mutual commitment to deploy a solution that will impact the problem 
LIVE  Customer has been onboarded: on time, within budget and the solution can deliver impact 
MRR  Solution delivers impact again and again and a recurring revenue stream is secured 
LTV The revenue an account generates over its lifetime, net of churn and including growth 
 
2. CONVERSION METRICS: ​Shows how effectively you are progressing leads and opportunities through 
the sales cycle (e.g., what is the lead-to-opportunity conversion rate, win rate, churn rate) 
CR1  PRO → MQL Prospect to MQL rate, indicative of the quality of the database  
CR2 MQL → SQL MQL to SQL rate, indicative of the quality of lead development campaigns 
CR3 SQL → SAL Showrate, hand-off, indicative of the quality of the prospecting work 
CR4 WR  Win rate, indicative of the quality of the total sales process and the sales skills 
CR5 Onboard Churn Churn during onboarding, indicative of quality of the client experience 
CR6 Usage Churn Indicative of the stickiness of the service; lack of impact results in churn 
CR7 Growth Upsell during usage during the length of the contract 
 
3. TIME METRICS: ​Shows how long it takes to move leads and opportunities through the stages of the 
sales cycle (e.g., time to first use, time to first value) 
ΔT1  Duration of prospecting before engagement is achieved, measured in days 
ΔT2 Duration of the prospecting campaign, indicates the quality of sequences used 
ΔT3 Time it takes to set up meetings and convert them into qualified opportunities (ideally <5 days) 
ΔT4  Sales cycle indicates the ability of a sales manager to navigate through the client’s process 
ΔT5 Time to live indicates the complexity of a product, anywhere from seconds to weeks 
ΔT6 Time until a client has achieved the desired impact, often a 12-month contract 
ΔT7 Time to achieve penetration of an account 
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CRITERIA  PROSPECT MQL SQL SAL WIN LIVE ARR LTV 
Is a fit Yes Yes Yes Yes Yes Yes Yes Yes 
Engageswith selected content Yes Yes Yes Yes Yes Yes Yes 
Meets with an expert to discuss impact Yes Yes Yes Yes Yes Yes 
Impact identified and we can solve it Yes Yes Yes Yes Yes 
Executed mutual commitment Yes Yes Yes Yes 
First impact achieved? Yes Yes Yes 
Recurring impact achieved? Yes Yes 
Total lifetime impact achieved? Yes 
   
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Creating Actionable Reporting Structure and Dashboards 
What metrics should be reported to each of your stakeholder audiences when you have a sales team in 
place with roles across the sales cycle? Use this as a guideline. 
 
Table 8.1​ Metrics that should be reported for each of your stakeholder types 
  EXECUTIVE/BOARD  SALES MANAGERS  SALES REPS 
Monthly 
(Board) 
Growth/Speed: 
(1) Pipeline created: SQLs per week 
(2) Pipeline developed:  
Win rate + ACV + Length of the 
Sales Cycle 
(3) Pipeline closed: MRR growth MoM + 
number of deals 
(4) Customer churn (logos and revenue) 
SaaS Metrics: 
 (1) Customer Acquisition Cost 
 (2) Lifetime Value/LTV 
 (3) Average contract length (months) 
 (4) Payback on CAC (months) 
 (5) Quota performance team 
Performance Metrics: 
MQLs/Campaign 
SQLs/SDR 
MRR/AE 
Deals/AE, Deals/SDR 
Sales Cycle/AE 
Win rate/AE 
 
Ramp:  
Time it takes from 
onboarding new rep to hitting 
80% of quota (<90 days for 
application, <180 days for 
platform) 
 
Performance Metrics: 
MQLs/Campaign 
SQLs/SDR 
MRR/AE 
Deals/AE, Deals/SDR 
Sales Cycle/AE 
Win rate/AE 
Weekly 
(Execs) 
Leading Indicators: 
- #MQLs, #SQLs 
Trailing indicators:  
- Deals, MRR 
MQLs/Campaign 
SQLs/Rep 
SQLs 
MRR/Rep 
Meetings/Demos 
Daily  N/A  Deals 
 
Email metrics 
Phone call metrics 
 
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EXPERT ADVICE ​Would you drive a car differently if we took away your speedometer 
and gave you only a fuel-efficiency meter? Research on the Toyota Prius suggests this is 
the case. In other words, the data displayed on the dashboard changes behavior. 
Remember this as you build your dashboard!  
JACCO VANDERKOOIJ 
Founder, Winning by Design 
Reporting to your Board 
Reporting to your board may always have some level of stress associated with it, but don’t let that stress 
come from creating dashboards and charts in the last hours before the board meeting. In the chart above, 
you will not have the data for all of those metrics right when you start out. So here are the metrics that you 
should be focusing on, by stage.  
 
Table 8.2​ Key metrics that you should be tracking and reporting on by stage (cumulative)  
  START UP  GROW UP  SCALE UP 
General  Revenue 
Deals won 
Pipeline of deals 
Inbound leads 
Website visitors 
Content/Event metrics 
 
Revenue + Bookings 
Forecast 30/60 days 
Inbound vs outbound leads 
Pipeline by stage 
Sales cycle (win/loss) in days 
SQL → Win (CR3xCR4) 
MQL → SQL (CR2) 
Revenue + Bookings + Cash 
Forecast 90/180 days 
Leads per campaign 
Pipeline generated/campaign 
Prospect ⇒ MQL (CR1) 
SQL → SAL (CR3) 
SAL → Win (CR4)  
Customer churn (logo, revenue)  
Growth from new logos 
Leadership    Average deal size 
Time to get to 80% of sales 
cycle 
 
Activities per Rep 
Deals per Rep 
Bookings per Rep 
Execs/Board  Focus: Key wins and 
Product-Market Fit 
Lost opportunities to 
understand why 
Focus: Sales effectiveness 
and Go To Market Fit 
metrics such as CAC, ACV, 
and Conversion Rates 
Focus: Sales efficiency and 
growth metrics, such as 
YoY/QoQ performance and 
# of reps reaching targets 
 
132 
 
 
Figure 8.2​ Example set of metrics for board and executive level reporting 
 
Below is an example of the level of detail that you can easily create in Excel or Google Sheets on each of 
those metrics listed above:  
  
133 
 
 
Figure 8.3​ Example of how to report growth in new logos 
 
 
Commons Questions 
 
Q: What comes first: SQL or SAL? 
A: In SaaS sales, ​first you qualify, then you accept. To clarify, think of a visit to the emergency room as an 
example.  
 
 
Figure 8.4​ Example of a visit to the emergency room  
 
   
134 
 
Q: We have lots of SQLs, but my sales team is not closing. Who is at fault?  
A: Look at the relationship between CR3 and CR4. ​Remember that CR3 is the conversion rate from 
SQL to SAL (shows the quality of the leads that the SDR has developed), and CR4 is the conversion rate 
from SAL to win (shows how effective the AE is at closing opportunities).  
 
There are a variety of reasons why opportunities are not closing:  
● No-shows: Prospects who commit to a meeting, but don’t show 
● Unqualified: Prospects who, upon further review, can’t be helped by us (at this time) 
 
Table 8.3​ Insights from a comparison of CR3 and CR4 win rates  
  CR3 
CR4  < 80%  ~ 90%  > 95% 
< 15%  Process issue: Cold calling with 
no relevance; train SDR on 
identifying leads who have a pain 
AE accepts too many leads; train 
on how to diagnose 
Train SDR to qualify with more 
rigor, and train AE to diagnose 
on priority 
~ 20%  Train SDR on identifying leads 
who have a pain 
Effective and efficient team; 
record and replicate the process 
Add an AE to the POD 
Too many leads 
> 25%  AE is only taking on deals that 
are ready to close 
Add another AE to your team  Add another sales POD 
 
Q: What is a healthy growth rate? 
A: A healthy growth rate is: 
 
 
EXPERT ADVICE ​If you think about growth from years one through three (from the 
moment you start to monetize)... 
 
 ​ Year 1 Year 2 Year 3 
Good growth rate:  $500K ARR → $1.2M ARR → $2.5M ARR 
Great growth rate:  $500K ARR → $1.5M ARR → $3.5M ARR 
Top growth rate:  $500K ARR → $2.0M ARR → $5.0M ARR 
135 
 
 
RYAN CAHILL 
Sales Architect, Winning by Design 
 
Q: I am not achieving the “triple triple double double” (3x 3x 2x 2x growth quarter over quarter). 
What is wrong with me? 
A: Nothing is wrong with you.​ Starting a company takes a lot longer than you think.  
 
 
 
Q: What is more important; Growth or profit? 
A: This is rapidly shifting. In 2015, it was growth at all costs.​ ​However, it’s now shifting to 
profitability. Investors no longer want to fund an unprofitable business. Up to $1M in ARR, you are still okay 
to tinker with your go-to-market model, but after that, you cannot spend more than 40% of the annual 
cost of marketing and sales in order to acquire new customers and revenue. In other words, the cost of 
marketing and sales cannot exceed 40% of your revenue. 
 
Q: Is monthly churn different from annual churn? 
A: Very different! ​With annual contracts (often for platform sales), customers churn at a much lower rate. 
A common churn for annual contracts is 5-8% (annually). For monthly contracts, between 1-2% (monthly). 
 
136 
 
 
 
Common Pitfalls 
 
Pitfall 1: Misunderstanding platform vs. application business. ​Benchmarks for KPIs of application 
sales compared to platform sales can be very different. Be sure that you are benchmarking your data 
against the right ones that apply to your business.  
Pitfall 2: Leaving board reporting to the last minute. ​Set up your format and agree with your 
executive team on what to report on and how. Set up an Excel or Google Sheets workbook well ahead of 
time, and set up a system so that your charts will automatically update with new data. Spend your prep 
time before boarding meetings thinking about the “why” behind the numbers, rather than stressing over 
data errors and chart formatting. 
 
   
137 
 
Sales Compensation 
Now that we know what metrics to watch, we can apply this to creating a sales compensation plan for the 
team. See here for an example of how this works for a POD with one SDR, 2 AEs and 1 CSM.  
 
 
 
Figure 8.5​ Calculating compensation for a POD 
 
   
138 
 
Here is how this translates into a compensation plan, this example for an SDR: 
 
Table 8.4​ Example structure of sales compensation for an SDR 
Title  Sales Development Rep  Seniority  Jr SDR [ ], SDR [ X ], Sr. SDR [ ] 
Reports to  Sr. Dir of PartnershipsQuota  Generate 20 SQLs per month 
On Target Earning  $ 60,000  Compensation Mix  75%, 25% 
Base Salary  $ 45,000  Sales Incentive  $ 15,000  
       
PLAN 
COMPONENTS 
PER SQL <= ACV<50K  PER HV SQL > 
ACV>$50K 
IF SQL ⇒ 
CONTRACT 
PAID 
Rate/Amount  $ 25 per SQL  $50 per SQL  $100 per Contract  Quarterly 
Cap  No Cap   
 
 
   
139 
 
 
   
140 
 
 
 
 
 
 
 
 
 
 
CHAPTER 9  
CULTURE 
 
 
   
141 
 
Why does culture matter?  
The sales culture you create is going to be one of the key components that determines if your company 
thrives, survives or dies. Every company will generate their unique sales culture that reflects their 
customers, founders and the company - but the high performing sales teams share a few common pillars 
of their culture that lead to success. 
 
EXPERT ADVICE ​Create a winning company strategy from Day One. That means 
putting customer centricity and team success at the center of your culture by clearly 
defining company-wide goals, a vision, and values that everyone is accountable for 
upholding. Being part of a bigger purpose will not only motivate employees to strive 
for excellence, but will also align the company with shared beliefs. This cultural 
accountability will prove its value during the most challenging quarters - when 
everyone roles up their sleeves and works together to meet or exceed goals.  
 
EMILIA D’ANZICA 
Sales Architect, Winning by Design 
 
Key pillars of culture 
There are four key pillars that you should adopt to realize a successful culture for your team:  
1. A clearly articulated company mission and revenue goals 
2. Science-based methods 
3. Strong organizational trust at all levels 
4. Objective coaching delivered to the team 
 
Clearly articulate your company mission and revenue goals 
 
Having a clear understanding of your organization’s ‘why’ is a key building block of your unique sales 
culture. This will enable you to hire the right candidates, shape your customer engagements and manage 
performance in a manner that aligns to your company values. For a quick and powerful primer on what it 
means to find the ‘why’, hear it directly from Simon Sinek in his TED Talk called “How Great Leaders 
Inspire Action”. 
142 
 
 
Be deliberate. Write down your ‘why’ and clearly communicate it to your sales team and to the candidates 
that you are recruiting. Once you have the ‘why,’ you must articulate sales goals and objectives that clearly 
align to your ‘why’ and the high-performing sales team will tie their goals to their efforts on a daily level. 
Why daily? Sales is a tough role that requires significant persistence in the face of rejection, so aligning 
your daily sales effort to the broader organizational objectives is key to creating a culture of learning and 
success. 
 
Adopt science-based methods for making decisions 
 
Let’s first talk about what is often the antithesis of a science-based culture. That would be a “superstar 
culture.” A superstar sales culture is one that relies on high-achieving individual contributors to win big 
deals. These superstars use enterprise-level sales skills developed and tuned over long years of 
experience.  
 
A science-based culture means getting scientific and specific with the numbers. This means identifying 
your target sales goal for the team, and then reverse engineering that process to identify the leading 
metrics that will lead to hitting that target. Keep in mind that in some instances, you will have new roles 
and won’t have a clear path of what the ‘math for success’ is. Using industry best practices, create a 
benchmark to work toward, and then refine from there. See below for an example of how this is done: 
 
   
143 
 
Table 9.1​ Assigning goals to each key metric in order to line up with the overall team goal 
SDR  Daily    Inside Sales  Weekly    Enterprise Sales  Monthly 
Prospect into cadences  50    Diagnose calls  10    Account plans  20 
Conversion rate  6%    Conversion rate  50%    Conversion rate  40% 
Conversations  3    Demonstrations  5    Opportunities  8 
Conversion rate  33%    Win rate  40%    Conversion rate  50% 
SQLs booked  1    Won deals  2    Proposals  4 
Conversion rate  0%          Win rate  25% 
            Won deals  1 
      ACV  $5,000    ACV  $150,000 
               
Monthly  20    Monthly  $43,333    Monthly  $75,000 
Annual  240    Annual  $520,000    Annual  $900,000 
 
   
144 
 
Build organizational trust at all levels 
 
A strong sales culture isn’t built by a single individual, manager or founder. It requires commitment across 
the entire team to continuous learning and using agile approaches to scale. Some keys to building 
organizational trust:  
 
● Building shared accountability:​ Encouraging individuals and teams to hold themselves 
accountable for their own actions. You will find that this becomes much more natural for teams if 
they see their leaders doing this themselves.  
● Displaying high emotional intelligence:​ ​Although we are engaging in a business environment, 
we are still human and need to take that into account with all interactions within the business. 
Everyone deals with challenges and opportunities differently. Take the time to understand your 
team and support their own approaches. 
● Supporting individual growth and success:​ We need both the organization and the individuals 
to be on a journey of continuous improvement. For the team, this means creating shared learning 
opportunities. For the individual, this means spending one-on-one time to understand their 
personal motivations, what they want to get out of their roles, and what skills they need to progress 
their careers.  
 
Deliver objective coaching to the team on an ongoing basis 
 
Sales managers and leaders often talk about themselves as sales experts who ​manage ​their teams. They 
are making the mistake of leaning too much on the word ​manager​. Managing people is actually an 
outdated approach to leadership. Instead, we need to ​coach ​our team members: This means creating a 
collaborative learning environment that continually evolves and learns through ​coaching​. How do you put 
this into practice? We recommend following the 70-20-10 principle.   
145 
 
 
Table 9.2​ The 70-20-10 principle for managing coaching time  
  70 - 20 - 10 PRINCIPLE 
10% 
Teaching 
- Regularly educate your team on your target customer and blueprints 
that enable them to have better conversations 
- Rely heavily on visualization of your processes and principles to drive 
engagement and conversation 
- Task your team members with teaching; you want to encourage people 
to see it, do it and teach it 
20% 
Coaching 
and 
learning 
from peers 
- Use our coaching guidance: coaching should be objective rather than 
subjective, based on the execution of the sales process 
- Coaching is not only on the shoulders of managers: everyone on the 
team should be empowered and educated on how to provide objective 
coaching feedback. This coaching needs to happen throughout the 
week, and should be a mix of formal and informal. 
70% 
Application 
- Reps will learn their skills and weaknesses when applying the learned 
skills in live and simulated environments 
- Learning and selling needs to happen concurrently and the best way to 
avoid the forgetting curve is through repetition 
 
 
Performance Management 
 
Here are some best practices for performance management and conducting reviews: 
 
● Weekly 1:1 pipeline reviews with a set weekly format for reading out accounts (see the Annex for 
the template) 
● Try to help solve roadblocks, rather than just talking through the details of an account 
● Keep in mind that the most common mistakes that reps make are:  
○ The AE wants to do it himself rather than ask for help from his manager 
○ There is only one contact/relationship with the account 
○ Not doing the basic blocking and tackling according to the sales process  
146 
 
● Common mistakes that salesmanagers make when conducting pipeline and performance:  
○ Not providing coaching on ​how ​to change their behavior, not just ​what ​to change  
○ Most problems here are related to process, not to people. Make sure that you have the 
right processes in place for your reps to follow for good pipeline hygiene. For example: 
What are the top five critical events you sell against? What impact are you creating for your 
customers? What are the use cases for different customers? 
○ Keeping coaching to themselves: Coaching should be owned by the team; senior reps 
should be coaching junior ones. Reps who have done a certain type of deal before should 
be coaching other reps on those deals. Managers should have the entire team take 
ownership of coaching and of elevating each other’s skills. 
● Group call review: Teams should review a minimum of two calls each week at the end of the week 
 
Commons Questions 
 
Q: Shouldn’t my sales managers manage the entire process, and not just the moments that 
matter? 
A: We hear you, but it’s these key moments that make the difference. ​Sales managers won’t have 
the bandwidth to micromanage the sales process for all of their reps - nor should they. They should only 
need to focus on these Moments that Matter, and that will make the difference.  
 
Q: Should I have my AE do prospecting? 
A: Depends on your ACV!​ In platform sales, the AE should do his own prospecting rather than an SDR 
prospecting and and then handing leads to the AE. In contrast, for high-velocity application sales (below 
~$15K ACV), you should likely be using a multi-role sales org (SDR prospecting and setting up meetings 
for the AE).  
 
   
147 
 
Table 9.3​ Who should do the prospecting based on your ACV 
ACV  STAGE 1  STAGE 2 
< $1K  Marketing develops the leads  Online order form 
< $10K (application)  Marketing develops the leads  Jr. AE closes 
$10K - 40K  SDR develops the leads  AE closes 
$40K + (platform)  AE develops the leads  Sr. AE closes 
 
Common Pitfalls 
 
Pitfall 1: Improper handoffs. ​It’s crucial to ensure that your different sales roles execute smooth 
handoffs (e.g., from AE to CSM/ONB as a customer is onboarding). These are important moments to the 
customer, and they must know that everyone at your organization is coordinated in working to help them.  
 
Pitfall 2: Reaching out to prospects who are a fit based on key demographics (e.g., title, 
location, etc.). ​This will send your company into overdrive, but it’s very ineffective. Doing so means you’re 
targeting using inefficient ‘fit’ characteristics, but not identifying the customers who actually have a ‘pain’. 
 
Pitfall 3: Treating the kickoff call for new customers simply as a time to get them onboarded 
with your product. ​When a lead has committed to you and become a paying customer, the kickoff call 
becomes a very important moment. This is the point at which your relationship with that customer has 
changed: you now have the shared goal of making them successful. Now is when you are setting the tone 
for your ongoing relationship with them. 
 
   
148 
 
How to structure coaching conversations 
 
 STEP 1 ​ ​Identify the types of meetings you need to conduct, and how often 
(d) daily, (w) weekly, (m) monthly, (q) quarterly 
 
INDIVIDUAL (1:1)  TEAM  MANAGING UP 
Business plan review (m) 
Personal development review (m) 
Pipeline review (w) 
Sales coaching (w) 
 
Standup routine (d) 
Pipeline update (w) 
Learning dojo (w) 
Business review (q) 
Executive roll-up (m/q) 
 
 STEP 2 ​ ​Set the duration and timing for your meetings 
Use the following table to help your team understand the expectations for each type of session.  
   
149 
 
Table 9.4​ The types of coaching meetings, and how they should be used  
MEETING  DURATION / 
FREQUENCY  
DESCRIPTION 
Business plan 
review 
60-90 mins 
monthly 
The rep should review his performance from the previous month, 
outlining the goals for the following month and plan to execute. 
Manager should challenge the rep, clear obstacles and coach towards 
a positive result. 
Personal 
Development 
30 mins  
monthly 
Manager works with the rep to define personal and career goals, and 
map against the rep’s current skill set. Rep should review what he has 
accomplished in personal development, and set goals for the coming 
month. 
Pipeline review  30 mins  
weekly 
Reps present their pipeline to the team, focusing on challenges. 
Managers should ask for details, understand why deals may have 
slipped, help to clear blockers, and identify possible missed 
opportunities to drive more customer value.  
Sales coaching  30 mins weekly  Discuss areas of opportunity and improvement that manager can 
determine from sitting in on live meetings, calls and onsite visits.  
Standup routine  15-30 mins  
daily 
A daily huddle between the team to review yesterday's performance, 
set intentions for the day and warm up with ‘ring-ring’ exercises. 
Pipeline update  45 mins  
weekly 
Review leaderboards from last week, review pipeline to close this 
week, and declare individual goals. 
Learning dojo  60 mins 
weekly 
A weekly session with a focus on increasing rep effectiveness. Focus 
areas should be identified by the team, guided by data. Sessions are 
to be run by individual reps and supervised/supported by the manager. 
Business review  60-90 mins  
quarterly 
The start of the quarter is an opportunity to align the team to business 
goals and inspire continuous improvement; review metrics with reps 
highlighting top five current and next period opportunities. 
Executive 
roll-up 
30 mins 
weekly 
Review current and next period forecast. Discuss target for current 
month and potential gap review, upsides and next steps. 
150 
 
 
 STEP 3 ​ ​Schedule your cadence for the week 
This might seem obvious, but don’t schedule meetings during ideal selling time: Take into account when 
your customers are available for meetings, and when your team will be most productive. Every sales team 
will settle on their own slightly different cadence, but here is an example to get you started. 
 
 
Figure 9.1​ A sample cadence of weekly recurring meetings 
 
   
151 
 
 STEP 4 ​ ​Map out your quarterly plan 
Apply the same guidelines to your quarterly plan by mapping out a cadence of your monthly and quarterly 
meetings.  
 
 
Figure 9.2​ A sample cadence across each week of individual, team and executive meetings 
 
   
152 
 
 STEP 5 ​ ​Create a sales coaching calendar 
 
Table 9.5​ A sample coaching calendar 
FREQUENCY  OBJECTIVE  TRAINING TOPIC  EXAMPLE THEME 
Quarterly  Review overall sales results and 
adjust your strategy. Set effort, 
knowledge and skills targets 
Review the need for any 
formal training on value 
proposition, customer 
campaigns or competition 
“Improve our win rates” 
Monthly  Set a specific improvement 
objective for each month related 
to the quarterly objective 
Review the results of your 
sales plays and make 
minor tweaks to 
sequences and plays 
Month 1: Discovery to demo 
conversion 
Month 2: Demo to proposal 
Month 3: Proposal to win 
Weekly  Review efforts and fine tune 
skills 
“Flight School”  
 Hands-on review of 
critical sales activities, 
such as account plans, 
proposals, recordings of 
discovery calls and demos 
Focus on a different aspect of a 
particular skill for narrow focus 
(e.g., call review) 
Week 1: Opening a call 
Week 2: Asking questions 
Week 3: Summarizing pains 
Daily  Practice through role-playing 
with each other 
15 minutes of role-play 
daily 
Day 1: Situational questions 
Day 2: Pain questions 
Day 3: Impact questions 
Day 4: Critical event questions 
 
 
 STEP 6 ​ ​Communicate with your team 
Key to ensuring success is to set the vision for what your team will be able to accomplish as a result of this 
schedule and rigor. Framing coaching as a collection of meetings doesn’t sound interesting or valuable. 
Rather, explaining how these sessions will help the teamup-level their skills, give them a better chance at 
meeting their goals and help the team be a highly tuned machine will motivate them to get involved and 
participate. 
   
153 
 
Hiring your Sales Leader 
 
Though culture comes from the entire team, it’s your sales leader who will certainly set the tone. Be sure to 
watch the video by Simon Sinek called “Why Leaders Eat Last”. It provides a great outline for a modern 
sales leadership culture, and Simon shows how it is based on four chemicals. 
 
 
Figure 9.3​ The four brain chemicals that drive behavior 
   
154 
 
Table 9.6​ A new kind of leadership 
ENDORPHINE  DOPAMINE  SEROTONIN  OXYTOCIN  
Makes you feel good so 
you can perform work. 
“Runner’s high” masks 
physical pain. Gives us 
consistent endurance. 
Positive feeling, drive. 
Makes you feel happy 
when you achieve 
something.  
Feeling of pride & status. 
We seek recognition. Gives 
confidence, and reinforces 
social structure and 
compassion for others.  
Feeling of love and trust, 
the warm and fuzzy feeling 
that someone has your 
back. Act of generosity 
based on time and effort. 
Makes you work hard.   Makes you goal driven.  Awards. Pride. Sense of 
allegiance, organization 
cohesion. 
Sacrifice time and energy 
to help team members. 
Have people perform and 
work at their own pace. 
Help them perform as a 
team. Let them practice 
with each other. Help 
them coach each other.  
Motivate people to 
achieve goals. Help them 
go after it. Check things 
off a “to do list.” 
Demonstrate progress to 
elevate team 
performance: ​Combined 
with $, this is ​addictive. 
Talk to them to share your 
thoughts instead of via 
email. Be accountable for 
mistakes made. Lead by 
example. “Show up.” 
Contagious: ​Spreads 
from one person to 
another.  
Let team members feel 
they make a difference. Sit 
down next to them and 
offer assistance. Make a 
call for them. Incentivize 
coaching with 
experiences. ​Infectious, 
(likely to spread). 
A more selfish, historic approach: 
Focuses on training 
Do the Work, Work hard, Achieve the goal, Get Paid 
A selfless, modern approach: 
Focuses on coaching 
Lead by Example, Give Time, Sacrifice, Share 
 
So when you are looking to hire a sales leader, be sure that you are looking for the candidate who has that 
selfless, modern approach - someone who will be a coach for your team, and not just someone who 
works hard. Here are a few more specific ways that this would manifest in behavior of a leader: 
● Motivating the team to work hard 
● Helping them achieve goals through shared work 
● Leading by example (not a desk jockey or a spreadsheet manager) 
● Actively developing and sharing best practices, and encouraging others to share 
● Helping team members elevate their skills by coaching rather than just fixing 
155 
 
● Getting the team to operate in a way that is greater than the sum of the individuals 
 
There’s so much more that goes into hiring your VP of Sales, and some organizations end up taking more 
than a year to find the right person. Be sure to work with your board and advisors to agree on the specific 
qualities and skills that your team needs; this will make the search process much faster and more effective.  
 
Common Questions 
 
Q: Why can’t I just hire a few superstar sales reps and let things ride? Won’t a great culture just 
naturally happen if you get high performing people?  
A: Yes - it will get you to $1-2M, ​but what gets you there will stand in your way to achieve the next level. 
You must plan for scale, and superstars don’t scale.  
 
Q: Should I set the corporate culture, or let the team set it? 
A: Many leaders believe they should set the culture as a reflection of themselves. ​This can be very 
hard on the people for the company. They will not work as hard as you do, they are not going to be as 
motivated, and they are not as stressed. You should put your personal stamp on the culture if you like, but 
the majority should come from the team.  
 
Q: Should I tweet my opinions about things not related to the company such as politics? 
A: This is a hot topic among sales leaders.​ There are two opposing points of view, both of which are 
valid: 
● You represent all people in your company - both the red and blue team. As such, you should never 
pick a side. This is the more politically correct (and common) leadership model. Here, we 
recommend that you focus 100% on the company with a few personality tweets. 
● Your people look to you to represent them. As such, they want you to voice their opinion in a 
balanced and composed way. Here, we recommend that you stick to signaling a few core 
principles that directly relate to what is going on in your world. 
 
This is a highly sensitive topic, and we suggest that you discuss it with your executive team. This topic can 
have positive or negative ramifications on hiring, tone, culture, etc. Do not just go out and voice your 
emotions.   
156 
 
 
Common Pitfalls 
 
Pitfall 1: Relying on a superstar sales culture.​ There is often a misconception that having “superstars” 
on the sales team is what contributes to a winning culture. Interestingly, the overwhelming majority of sales 
teams out there rely on superstars to deliver 80% of their results. It’s easy to think that the best way to 
grow and scale is to hire as many superstars as you can. What could be wrong with that, right? Nothing to 
get you to the first $1M or even $2M in ARR. But companies with this type of sales culture will inevitably be 
dependent on a single performer: at first, it’s the Founder CEO, who trains only sporadically (if at all), and 
will incorporate little discipline and methodology into their operations. When this type of organization tries 
to scale, the entire system breaks down, because there is nothing to scale. Instead, successful 
high-growth companies should make the transition to a process culture, followed by using technology to 
act as a force multiplier, and then enablement, skills, and finally the team. 
 
 
 
Figure 9.4​ The Superstar culture may get you to $5M, but you need a Science culture to scale beyond $5M 
157 
 
 
Pitfall 2: Alpha sales leader in a team culture. ​The alpha sales leader is going to focus more on the 
individual rather than the team. They will certainly follow the general concept of ‘work hard, hit goal, get 
paid’ but you actually need someone who focuses on collaboration, helping each other, and shared 
success. That’s the sauce that leads to a sustainable sales culture where team members feel supported 
and will want to stay.  
 
Pitfall 3: Coffee machine startup culture.​ Lots of startups are making their office spaces look and feel 
like a high-end hipster coffee house, and that will attract employees who place importance on that 
environment (and therefore spending 1.5 hours sipping a latte each day). Obviously, you want your office 
space to be welcoming - but make sure that your space doesn’t go overboard. The appearance of the 
space can easily start to manifest in your team culture.  
 
Pitfall 4: No deep work space.​ The open floor space, while it’s all the rage these days, doesn’t allow for 
‘deep work’. People interrupt each other, the coffee machine is brewing, the TV is showing news, people 
are talking! Super cool, but no deep work happens - such as focusing on researching a key account, 
writing a proposal, calculating a price, and so on. Think about dedicating a ‘library room’ where employees 
can go for undisturbed deep work (think of the ‘no talking’ area in a public library, or the train’s ‘quiet car’).  
 
Pitfall 5: Urgent vs. Important.​ Early stage companies often struggle to recognize the difference. We 
recommend that as an executive team, you spend time discussing this to determine at a high level which 
is which.  
   
158 
 
Table 9.7​ How to think about and prioritize what is urgent versus what is important 
 
 
 
 
 
I 
M 
P 
O 
R 
T 
A 
N 
T 
URGENT  NOT URGENT 
MANAGE 
QUADRANTOF NECESSITY 
These are the daily tasks that are high 
priority, needing a sense of urgency - 
and completely necessary for 
performance in your role: 
 
● Return phone calls 
● Calendar meetings/send invites 
● Check LinkedIn visits 
● Discovery calls prior to demo 
● Deadline-driven projects 
● Schedule internal meetings 
 
FOCUS 
QUADRANT OF QUALITY 
These are the daily tasks that, if you do not 
write them down, you will forget about. And
forgetting about them will cost you 2x more
time the next day: 
 
● Planning your day/week 
● Studying your use cases 
● Playing with your own product 
● Account prep/updating CRM 
● Quiet time/break time 
● Responding to flagged emails 
● Focusing on key accounts 
● SDR/AE conversations 
 
 
N 
O 
T 
 
I 
M 
P 
O 
R 
T 
A 
N 
T 
MITIGATE 
QUADRANT OF DISTRACTION 
While you may feel these activities need 
your attention right away, this is where 
you get distracted and spend too much 
Temper these activities by setting strict 
time limits per day: 
 
● Chatting (Slack, GChat etc.) 
● Social media updating 
● Checking and answering emails 
● Most 60-minute meetings 
● Writing reports 
 
AVOID 
QUADRANT OF WASTE 
Many of the activities in this quadrant are 
well-known to eat up your time. Know that 
engaging in too many of these activities is 
what causes stress in your life every day: 
 
● Texting 
● Surfing, online shopping 
● Excessive breaks/long lunches 
● Selecting your music list 
● Chatting 15 mins with 20 people every 
day 
 
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160