The 31 Best Sales Leadership Books of All Time

The 31 Best Sales Leadership Books of All Time

Chris Orlob
September 8, 2022

These are the best sales leadership books for your reading list.

I wrote this post because there is little education on sales leadership.

But these books stand out.

Throughout my career, I’ve been a voracious reader. I credit much of the success I’ve enjoyed so far to that habit.

Of all the different types of books I've read, sales leadership books have been the most common.

The Best Sales Leadership Books

When people learn of my “manic habit” of reading, they ask me which ones are the best sales leadership books.

More than any specific books, I’d recommend picking up the habit of reading to begin with.

I’ve read every one of the below sales leadership books from cover to cover.

Here are my summaries.

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1. The Qualified Sales Leader

John McMahon is the only person the planet to be CRO of five public companies. He is a legend of enterprise software sales and known to have invented MEDDPICC. John writes this book by telling a story. This is by far my favorite sales leadership book, and people are loving it. He has dozens of tips, tactics, and timelines pieces of wisdom throughout the stories he tells.

2. The Sales Acceleration Formula

Mark Roberge was one of the first employees at Hubspot and grew the company to $100M ARR as CRO. Mark talks about a key topics all sales managers need to know: hiring, coaching, training, and motivating your sales team. All in "formula" style.

3. The Sales Manager Survival Guide

David Brock is one of the most blunt sales leadership educators you’ll meet, in the best way possible. He tells it like it is, and stays true to that posture in his book. You’ll learn about the mechanics of being a great frontline sales manager. Everything you SHOULD know when you become a manager for the first time. Coaching, pipeline reviews, how to run deal strategy, hiring, and more. Beyond mechanics, David does a great job with timeless leadership wisdom.

4. Sales Management. Simplified.

Mike Weinberg also presents himself in a direct, no bullshit way. Refreshing. Mike has a knack for distilling sales management into the key parts that drive success. There’s a lot to being a sales manager. Mike boils it down to the essentials.

5. Cracking the Sales Management Code

Cracking the Sales Management code is all about sales metrics. That sounds simple, but it’s an incredibly important aspect of being a sales leader. The right metrics drive the business. Jason Jordan breaks down metrics into hierarchies. Business results (the big picture goals of the business). Sales objectives (what you need to achieve form a sales standpoint to achieve the business results). And activities that drive it all.

6. Topgrading for Sales

There’s Topgrading, and there’s Topgrading for Sales. Both are great. This book teaches you a framework for identifying your ideal rep profile and running a chronological interview. Both of which predict whether a rep will be successful.

Before you move on, since we’re talking about sales hiring skills, grab our FREE cheat sheet of 91 proven interview questions.

7. Aligning Strategy and Sales

Frank Cespedes is a Harvard Professor that focuses on B2B sales. This book is for those who want to take their sales leadership career into the executive ranks. He talks about business strategy topics, such as market strategy, product strategy. And how to bring those strategies to fruition through a strategy-aligned sales team.

8. Crucial Conversations

This is not a sales leadership book, per se. But it applies to sales leaders better than any other profession. It's about how to have hard conversations with people and maintain the relationship. For sales leaders, that means performance management, holding people accountable, disciplining people. A huge part of being a sales leader is having hard conversations. This book provides frameworks for that.

9. More Than a Number

Scott Leese is a serial VP Sales and SVP Sales. He is VERY well known to be an expert senior sales leader who scales startups to hundreds of reps. More Than a Number is “the” book for first-time VPs of Sales. Indeed, it is a handbook for becoming a VP Sales.

10. First, Break All the Rules

Another book that’s not a sales leadership book, but great for sales leaders. This book is about people management. It helps sales managers know how to identify talent, and transform that talent into sales results. That’s what sales leaders do.

11. Sales Management That Works

This is the second appearance Frank Cespedes has on this list. In this book, he does a great job zooming in and out between the big-picture aspects of sales leadership, and getting down to the details sales leaders need to do their job on a day to day basis.

12. 42 Rules to Increase Sales Effectiveness

A short book with 42 small chapters, each written by a different, experienced sales and business leader. It’s a collection of tips for running a more effective sales organization.

13. What Your CEO Needs to Know about Sales Compensation

Very few sales leaders are well-versed when it comes to sales compensation. This book will fix that. It helps you understand how to use comp plans to achieve strategic and opportunistic objectives. It also talks about the limits of comp as a management tool.

14. The Ultimate Sales Training Success Guide

I have to admit, this author’s writing style in this one grates me. BUT… this has been one of the most useful books I’ve used throughout my career. It teaches you a framework for how to design great sales trainings. I’ve used the frameworks dozens of times, and they work so well that reps rave about my trainings. I owe much of my success to this book.

15. Revenue Harvest

This is a short book from an experienced sales leader who draws an analogy between sales leadership and reaping a great harvest as a farmer. How to plan and execute your sales year. From planting seeds (hiring great people, coaching them, etc.) to reaping the rewards (hitting your annual number). To doing it all over again the next year.

16. Never Hire a Bad Salesperson Again

If you feel light on your sales hiring skills, this book is a great place to start (along with the SaaS Sales Hiring Masterclass). It teaches you the fundamentals of behavioral interviewing: how to identify traits in candidates that lead to sales success, based on well-crafted, sales-oriented, behavioral interview questions.

Grab our FREE cheat sheet of 91 proven interview questions.

17. The Culture Code

Notice a pattern with this list of sales leadership books? Many of them aren’t sales leadership books. But they’re books that will make sales leaders far more successful if you read and apply them. This is another one. It teaches you how to create a winning culture for your team. Very applicable for building a thriving sales team.

18. Own Your Day

Keith Rosen makes it on this list a few times. This is his first appearance. Sales leaders have unique challenges when it comes to time management. This is a short book that helps sales leaders address unique time management challenges.

19. Traction

Traction is a book best-read by 2nd line sales leaders (and above). It’s less about sales leadership and more about how to run a successful organization. I used the the principles during my time as a 2nd-line leader to align my frontline managers and build an operating cadence.

20. The Sales Coach’s Playbook

This is one from a Sandler trainer. As you’d expect, it’s a coaching methodology influenced by the Sandler methodology. It talks about question-based coaching, and how coaching and training are different things.

21. From Selling to Managing

If you’re a new manager transitioning from an individual contributor role to sales manager, this is a great read. It talks about how what made you successful as a rep can be counterproductive as a manager. And how to make the transition.

22. Make Winning a Habit

This book is about deal strategy and sales leadership. It’s one of my favorites. It comes from the author of Hope Is Not a Strategy, which is one of the better books on enterprise selling and competitive deals around. Both books are underrated.

23. Coaching Salespeople Into Sales Champions, and Sales Leadership

Here’s a “two for one” for you. Both Coaching Salespeople Into Sales Champions and Sales Leadership by Keith Rosen are excellent books on sales coaching methodology. I’m coupling them together because they are both similar and build on each other. These books does not address much outside of sales coaching, but goes very deep on that topic. Coaching Salespeople Into Sales Champions also has an AWESOME appendix at the end of coaching questions sorted by issue and topic. They’re great.

24. ProActive Sales Management

Skip Miller wrote a few great sales books (including Selling Above and Below the Line). His sales management book, ProActive Sales Management, is just as great. It talks about the foundations of being an effective sales manager, and how to operate from proactive posture despite occupying a role that can deteriorate into reactivity VERY easily.

25. The Complete Guide to Accelerating Sales Performance

I have to warn you about this one: It’s written by academics, and it reads that way (it’s pretty dry). But it’s a solid book when it comes to the comprehensiveness of what sales leaders should be thinking about to drive revenue. From coaching, to hiring, to sales compensation, and even sales strategy.

26. Nuts and Bolts of Sales Management

This was the first sales management book I read. It is GREAT if you’re looking for a solid list of sales management and sales leadership tips and techniques. That’s how you can think about this one. It’s not comprehensive and doesn’t provide frameworks or methods. But it’s a great picklist of helping tips.

27. The Ultimate Sales Manager’s Guide

I listened to this one on Audible. The author’s passion for sales leadership comes through his voice. He talks about everything a frontline sales manager would need to do her job successfully. He talks a lot about running great team meetings, training sessions, and “practice sessions” with your team. GREAT guide for frontline sales managers.

28. Build a Winning Sales Management Team

This is another book written by academics (with the dry style to go with it). I believe by the same authors mentioned above. It provides theories for 2nd- and 3rd-line sales leaders to use to build their layer of sales management into a winning team.

29. The Sales Boss

I was skeptical of this one at first. Mainly because I don’t like the title (“boss” gives me mixed emotions). But it turned out to be an incredible book. Especially for sales managers that are starting at new companies


30. The Accidental Sales Manager

This book describes what happened to a lot of us: We got into sales (and then sales leadership) by accident. Fw of us are well-trained as sales leaders (which was the original inspiration to start creating video courses on QuotaSignal). This book helps solve that by giving you the foundations of being a great sales manager in a world where those foundations are lacking.

31. The Sales Manager’s Guide to Greatness

I read this one early in my sales leadership career, and loved it. I still do. The book is underrated and deserves more attention. It talks you through 10 strategies sales leaders can use to achieve greatness.

Which Sales Leadership Books are Missing?

I’m sure there are plenty of sales management and sales leadership books that are missing from this list.

But one person can only read so much!

I’ve only included sales leadership books that I’ve read.

So help me complete the list!

Which sales leadership and sales management books are missing?

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