I've spent the better part of twenty years in revenue roles — minor league hockey, minor league baseball, NASCAR, and now Italian football at the Serie A level. The titles have changed. The industries have changed. The size of the organisations has changed. But the fundamental challenge has stayed the same: how do you build a team, a culture, and a system that generates sustainable revenue growth, year after year, regardless of what's happening around you?
I've read a lot of books looking for answers to that question. Most of them were fine. Some were forgettable. A handful changed how I work.
These are five of those.
1. Start With Why — Simon Sinek
Every revenue team I've ever led has had the same problem at some point: people who are technically competent but can't articulate why the thing they're selling matters. They know the product. They know the price. They don't know the why — and neither, often, does the organisation they work for.
Sinek's central argument is deceptively simple: people don't buy what you do, they buy why you do it. The companies and leaders who communicate from the inside out — starting with purpose, then moving to how, then what — consistently outperform those who lead with features and benefits.
I've used the Golden Circle framework in every sales culture I've built since reading this book. It's the foundation of how I approach onboarding, how I train salespeople to have discovery conversations, and how I think about positioning. If your team can't answer "why does this organisation exist and why does it matter?" in thirty seconds, this is the book to start with.
2. Good to Great — Jim Collins
Collins and his research team spent five years studying companies that made the leap from good to sustained greatness — and, more importantly, studying the ones that didn't. The result is one of the most rigorous books on organisational performance ever written.
The concept that has stayed with me longest is the Hedgehog Concept: the intersection of what you're deeply passionate about, what you can be the best in the world at, and what drives your economic engine. Most organisations — and most revenue teams — operate somewhere outside that intersection. They chase revenue in areas where they have no right to win, or they build systems around activities they're not actually good at.
As a revenue leader, I've used this framework to make some of the most important decisions of my career — including what not to pursue. That discipline is harder than it sounds, and Collins explains why better than anyone.
3. Delivering Happiness — Tony Hsieh
Hsieh built Zappos into a billion-dollar business by treating company culture as the product. The thesis is that if you get the culture right, everything else — customer service, employee retention, revenue growth — follows from it.
I came to this book sceptical. Culture is one of those words that gets used so often in business that it starts to lose meaning. Hsieh gave it meaning back. What he built at Zappos wasn't a set of values printed on a wall. It was a set of behaviours, hiring decisions, and operating principles that were so deeply embedded that the culture became self-reinforcing.
The chapter on core values — specifically how Zappos arrived at theirs and what they actually did with them — is something I've returned to every time I've joined a new organisation. Revenue is downstream of culture. This book is the clearest argument I've read for why that's true.
4. The Infinite Game — Simon Sinek
Sinek appears twice on this list, which tells you something. The Infinite Game is the book I wish I'd had earlier in my career, when I was optimising for quarterly numbers at the expense of things that were harder to measure.
The distinction Sinek draws is between finite players — who play to win, to beat the competition, to hit the target — and infinite players, who play to keep playing. Most business is treated as a finite game. Most of the damage done in organisations — the short-termism, the culture erosion, the talent attrition — comes from applying finite-game thinking to an infinite-game context.
As a revenue leader, you are always being evaluated on short-term metrics. That's not going to change. But the leaders who build something durable are the ones who hold both frames simultaneously — who hit the number and protect the culture, who close the deal and invest in the relationship. This book gave me the language to articulate that balance, which made it easier to defend.
5. The 7 Habits of Highly Effective People — Stephen R. Covey
I've included this one not because it's the most sophisticated book on the list — it isn't — but because it's the most foundational. Covey's framework for personal effectiveness underpins almost everything else I've read about leadership and performance.
The habit that has had the most practical impact on my work is Habit 5: Seek first to understand, then to be understood. In revenue roles, there is constant pressure to talk — to pitch, to present, to persuade. The leaders who are actually effective are the ones who listen first. They understand the problem before they offer the solution. They know what the customer, the stakeholder, or the team member actually needs before they start selling.
I've watched this habit separate good salespeople from great ones more reliably than any other single behaviour. If you're building a revenue team and you could only give them one book, this might be it.
These five books aren't a complete curriculum. There are others I'd add — The Obstacle Is the Way for resilience, Atomic Habits for building the systems that make consistent performance possible, Outliers for understanding the role of environment and opportunity in success. But if I had to start somewhere, I'd start here.
Revenue leadership is ultimately about people — understanding them, motivating them, building environments where they can do their best work. The books that have helped me most are the ones that took that seriously.
— Ryan