The CRO Playbook

The CRO Playbook is the guide that I wish I had when I first became a Chief Revenue Officer (CRO).  It includes all of the tools, templates, and resources that a new CRO at a startup or growth-stage company needs to successfully create and execute on an ambitious revenue growth plan.

Since I stepped out of my role as a CRO to teach sales at the Ivey Business School, I’ve been inundated with messages of support from the sales community praising higher education’s interest and investment in the revenue generation function (Thanks to Ivey for trusting me to kick-start this program!).  My inaugural sales-focused course, Sales Foundations, launched in 2020 and has since become one of the most popular electives at the business school.  Every year I have the pleasure of teaching hundreds of our country’s brightest young minds the foundational selling skills that will make them more effective in their roles no matter what position or company they find themselves working in after graduation.

The messages of support from the sales community were, candidly, not surprising: despite the overwhelming interest in sales as a career choice for undergraduate students, and demonstrable value of sales skills in any role (consultant, accountant, or investment banker), higher ed has chronically underinvested in this area for a variety of reasons that I’ve covered in a previous post.

What did surprise me, however, was the volume of emails, texts, and direct messages that I received from sales professionals asking for help with their sales and growth-related challenges.  When I announced that I was moving from operating a business, and leading a revenue team to teaching at a business school, and investing in start-ups, it was as if suddenly I was expected to have the solution to any and all sales-related challenges.

I read messages from founders and start-up CEOs who had just raised big fundraising rounds and wanted to know how to deliver on their (huge) promises.  I read emails from next-generation owners of family businesses wanting to build on their family legacy, or turn around their family businesses.  I even heard from consultants or investment bankers turned-partners who were suddenly responsible for generating revenue for their firms.  They all wanted to know “the answer” to their sales challenges.

Who I heard from most, however, was first-time sales leaders or CROs (Chief Revenue Officers) wanting “a quick meeting” to talk sales strategy, share their approach, ask me some questions, or glean best practices - all in the hopes of giving them an edge in their new roles.  

To me, this made sense.  

I had spent the last decade being responsible for revenue generation at several early and growth-stage companies, and now that I was teaching at Ivey, surely I had the “secret sauce”.  Didn’t I?

Through these conversations what I realized was that while reflecting on my own experiences was helpful, I couldn’t confidently provide “the right answers” across all industries, stages of company, or geography.  I found myself asking a lot of questions, providing some suggestions and frameworks or resources, and sending them back out into the jungle with a sharpened machete when what they needed was a map.

After each call, I found myself flipping through my notebooks in an attempt to remember what I’d done to successfully navigate a similar challenge, and often I’d end up digging through academic journals to figure out if what I did was indeed the “right” move, or if it was just lucky.  

Through these conversations, I started to develop interesting and useful answers based on my personal experiences, interviews that I was conducting with other sales leaders, and conducting extensive research into the literature.  

After spending hundreds of hours on these calls with real sales managers, conducting my own research, and teaching these concepts in my own classes, coaching sessions and executive workshops, my aim is to bundle up some of the key lessons and share them with the next generation of CROs and sales or revenue leaders.

This is my objective with this series of posts.

My hope is that this guide can help new CRO’s avoid a lot of the “lessons learned” (mistakes) that I, and other CRO’s have made in the past.  I’m not suggesting you won’t make mistakes, but you’ll make new ones instead of repeating the same ones that pop up over and over again with new sales leaders.  I’ll combine real case studies and experiences with peer-reviewed academic research to answer some of the most pertinent questions on the minds of new CROs, CEOs and sales leaders.

To do that, first, I’ll take you through my experience as a CRO and what it felt like to have the weight of the world on my shoulders as a partner at a fragile early-stage company with new investors and enormous expectations.  I felt the pressure of almost a hundred employees who are counting on me to deliver on my promise to grow revenue  and put cash in the bank.  My partners put their faith in me.  And perhaps the most weight I felt was the pressure that I put on myself to prove that I was capable of delivering value, and capable of proving myself to the world.

Next, I’ll provide an overview of the revenue function and how it has changed over the last decade.  I’ll talk about the revenue machine, how it works, and provide an overview of common sales terms that you need to know to understand startups and scale-ups broadly, and revenue generation teams specifically.  Lastly, in this section I’ll outline the various roles on a revenue generation team and their respective responsibilities as well as when to hire for each.

Next, I’ll identify the most common “start-up killers”: the equivalent of the widow-maker in the startup and scale-up world. There are infinite ways to royally screw up in the role of a CRO, but most of those screwups can be fixed, even if they cost you time and money.  However, there are a handful of mistakes that will kill a company, full-stop.  Job number one for a CRO is to avoid these fatal mistakes at all costs.   I’ll identify what they are, and show you how to steer clear.

After you understand the role and what not to do, I’ll provide a framework for how to approach your first 90 days in a CRO or Head of Sales role starting with how to make an effective transition from founder-led sales.  I’ll cover topics like:

  • How to understand the pain points and buying motivations of early-stage customers
  • How to build your first revenue plan and sales playbook
  • How to build your first buyer journey map and a corresponding sales process as well as when to modify it
  • How to create a sales forecast and budget
  • How to build your team: hiring, firing, coaching and compensation
  • How to set up a CRM and reporting system
  • How to measure success and share progress on your goals with the CEO, your team and the Board
  • And of course: how to bring in your first early-stage customers, and start making money.

In this guide, I’ll provide the templates I used, and the most helpful resources that I’ve found on the above topics.  

Where this guide differs from other resources is that I’ll include examples, case studies, and research to add context and credibility.  This guide isn’t just stories from my own experience, it’s based on peer-reviewed academic research, and the real life experiences of other CROs and sales leaders who have been through the journey before at various stages, and in various industries. 

Finally, I want to spend some time on how to prepare you mentally, physically, and spiritually for this undertaking.  This is a role that requires incredible time, and attention, and can consume you - as it did to me.  If you’re not careful, it can lead to a dark place and I want to offer a sort of “resilience toolkit” to make you not just a great CRO, but also a great partner, friend, parent, volunteer, or whatever else is in your life that makes you a whole functioning human as you start your journey.  Because at the end of it if you’re a great CRO but have given up everything else in the process, I think you’ll be left ultimately unfulfilled.

Why do all this?

Firstly, I have a passion for teaching.  To teach, you have to first spend time thinking about and understanding a topic deeply, which I believe requires real-life experience, time and space to reflect, as well as patience to augment or validate those experiences with peer-reviewed research.   I enjoy reading and curating the research (I’m a unique breed), and and I do my best thinking through writing.  All of this ultimately makes me a better teacher.

Second, this is a large part of my life’s work.  My partner and I have had the good fortune of starting, growing, and exiting several startups and scale-ups, and these conversations have become regular banter around the dinner table.  I’ve lived and worked in some thriving startup ecosystems (New York, San Francisco, and Toronto) and feel an obligation to leverage my experiences to help the next generation of builders and sellers.  If this guide plays a small part in the start-up or growth story of the next Google, Amazon, or Netflix that then goes on to employ thousands of people and puts a dent in the universe, that’s work to be proud of.

Finally, in my own research I’ve found that a lot of these types of guides have an ulterior motive: typically it’s an article written by a junior content marketing manager for the sole purpose of ranking for a keyword so that a fraction of a percent of the people who visit the website buy whatever software they’re selling.  Inbound marketing, I get it.  But this guide isn’t about that.  I didn’t start with keyword research to optimize the articles to show up on the first page of Google, and I didn’t over-engineer the titles for dopamine hits.  I wrote this for the sole purpose of helping this next generation of CROs be better than the last, and my hope is that if the content is relevant, applicable, and most importantly actually works, then people will share it and recommend it organically.  And if only a handful of people find it, apply the principles, and crush it as a CRO then we’ll keep it as our little secret.

Stay tuned for the first article in the series, From Faking it to Making it in a New Role.


If you want to learn about the next article in the series, you can sign up for my mailing list and I’ll e-mail you directly when it comes out.  

And finally if you think this series might be valuable for someone that you know, please forward it to them - I’d really appreciate it.

Let’s grow.

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