The Top 11 Sales Books for Startup Founders

Startup founders are no strangers to figuring things out as they go. Building a sales organization from scratch in a new company selling a novel technology in an often nascent industry comes with its fair share of ambiguity.

Thankfully, the sales skillset is arguably as old as communication itself; there are countless gems of information to be gained from the experiences of the world’s top performing entrepreneurs and sales professionals.

The following list will introduce you to the tactical strategies in some of the startup world’s biggest sales success stories, such as Salesforce.com and Zenefits, as well as some highly valuable reads for any professional.

How to Win Friends and Influence People - Dale Carnegie

A far cry from being just some self-help book, How to Win Friends and Influence People has a place in every professional’s toolbox. Carnegie masterfully outlines the basic tenets of leadership and influence in an organization.

This book has sections like:

  1. Fundamental techniques in handling people, such as giving honest and sincere appreciation.

  2. Ways ways to “make people like you,” such as simple ways like smiling to using the other person’s name frequently

  3. Ways to win people to your power of thinking, such as being friendly and being sympathetic to the other person’s ideas

  4. Strategies for being a leader, such as letting the other person save face and praising every improvement.

Any founder can benefit from reading it at regular intervals throughout their startup journey.

The Sales Acceleration Formula - Mark Roberge

The Sales Acceleration Formula opens with a big promise: how to use data-based inbound selling to scale an organization from $0 to over $100 million– and it delivers.

As the SVP of Worldwide Sales and Services for HubSpot, author Mark Roberge helped his company acquire and retain its first 10,000 customers over more than 60 countries. In this book, Roberge outlines his unique methodology.

The book dives deeper into the following concepts:

  • The Sales Hiring Formula: How to hire the best possible salesperson every time. The Sales Training Formula: How to scale your sales training

  • The Sales Management Formula: How to keep your sales team accountable

  • The Demand Generation Formula: How to give your sales team the same high-quality and quantity of leads on a regular basis.

  • How to leverage technology to improve the buying process for customers and facilitate sales for your team.

This book is particularly salient for founders because Roberg uses his MIT engineering background to challenge conventional scaling methods with the metrics-driven process he refined while at Hubspot. After reading this book, founders can expect to become better at utilizing data and technology to improve every element of their inbound sales– from hiring, training, and managing your sales team to generating demand for your products.

The Go-Giver - Bob Burg & John David Mann

At about 144 pages, The Go-Giver is a quick and lightweight fictional read that delivers a powerful message: the protagonist learns how to change his focus from getting to giving, and by doing so, he’s met with unexpected returns.

The Go-Giver is an excellent vehicle for explaining concepts such as value, influence, authenticity, reciprocity, and fair compensation, all while tethering the story to an up-lifting applicable message.

Predictable Revenue - Aaron Ross

Predictable Revenue borrows from Salesforce.com, an absolute beast of an organization that has dominated its industry for over a decade. The book focuses on helping founders build a sales machine from the ground up, and includes topics such as:

  • How to build an outbound sales process without traditional cold calls or a marketing budget to generate a 9% response rate.

  • The seven fatal mistakes Sales VPs and CEOs make, and how to avoid them

  • How to build self-managing sales teams and turn your employees into “mini-CEOs”

It’s an absolute foundational must-read at this point in time. The name alone is enough to capture the eyes of any entrepreneur looking to increase their startup valuation with consistent revenue growth. The book goes over the outbound sales process that helped Salesforce capture over $100 million in recurring revenue, nearly doubling their enterprise revenue with zero cold calls.

SPIN Selling - Neil Rackham

SPIN Selling revolves around the straightforward strategy of SPIN (Situation, Problem, Implication, Need payoff).

Author Neil Rackham was the President and Founder of Huthwaite corporation, where he helped uncover the SPIN principles in a 12-year $1 million in-house research push.

If you’ve been trying and failing to repeat sales strategies that were otherwise successful for smaller-cost sales while selling higher-ticket items, SPIN Selling will be an enlightening read. Rackham teaches founders how to increase their sales volume from major accounts and how to sell high-value products and services.

The magic of SPIN Selling is that it dives into the tactical and granular aspects of big sales and is based on examining historically successful real-world sales calls in the field.

Zig Ziglar’s Secrets of Closing The Sale - Zig Ziglar

Any one of Zig Ziglar’s books can go down as a perennial sales read classic, and they’re often recommended by Sales VPs to their entire organization–within and outside of sales. The Secrets of Closing The Sale is one of the best books for startup founders.

The Secrets of Closing The Sale is gold for any founder looking to break through the bottom of the fun obstacles and ultimately lift the overall conversion rate of their organization. The book contains:

  1. 100+ successful closing examples that showcase excellent execution for any kind of persuasion.

  2. 700+ questions to stimulate a reinvention of your sales process and any new potential value you may be leaving on the table in your negotiations.

  3. How to use your words to illustrate a successful future with your prospects and get more results.

The Challenger Sale - Matthew Dixon & Brent Adamson

Authors Matthew Dixon and Brent Adamson set out to investigate the behaviors, attitudes, and skills shared among the highest performing salespeople and they uncovered a fairly contrarian potential for upside: challenging the relationship.

Adamson and Dixon highlight how an average-performing salesperson can close more deals and increase customer loyalty by challenging and reframing customer expectations and engineering a more resonant purchase experience.

The Challenger Sale outlines five distinct sales profiles, but ultimately posits that “the Challenger” is capable of producing consistently high performance.

This is another foundational book that is recommended for founders and salespeople alike. Founders can benefit from reading this book by not only challenging their own assumptions to sales relationship-building, but also to prototype how to recruit and train power players within to scale their enterprise sales efforts.

Never Split The Difference - Chris Voss & Tahl Raz

Never Split the Difference is a world-renowned business book and simply cannot be missed by any founder looking to make a positive material impact on their startup. 

Chris Voss borrows lessons from his career in the FBI as an international hostage negotiator to teach professionals from all walks of life how to successfully navigate high-stakes negotiations.

Co-author Tahl Raz also has a knack for refining hyper-critical business lessons from great stories around the world, and partners with Chris Voss to deliver a highly actionable approach to negotiations– whether that be a highly impactful sale with a big-name client, terms with a potential investor, or even just for new office space rent.

From Impossible To Inevitable - Aaron Ross & Jason Lemkin

From Impossible to Inevitable outlines the playbooks of companies that have achieved 100x growth, and the proper strategy and excellent sales execution they used to get there.

Authors Jason Lemkin and Aaron Ross explore how companies like Zenefits ($1m to $100m in two years), EchoSign ($0 to $144m in seven years), and Saleforce.com have been able to achieve hyper-growth in relatively short windows of time. The book goes through concepts like:

  1. Developing a culture of initiative through employee ownership.

  2. Doubling your deal size rather than solely focusing on scaling your deal quantity.

  3. Prime your organization for growth by building a strong foundation.

If you’re a founder looking to 10x your revenue, the templates and guidance in From Impossible to Inevitable can go a long way in guiding you towards your fast-tracked period of growth.

To Sell is Human - Daniel Pink

Daniel Pink has a talent for breaking down otherwise complicated or nebulous concepts into an actionable and easily digestible science.

Using a deep well of insights gleaned from social sciences, Pink uncovers some fairly counterintuitive insights for closing deals.

To Sell is Human describes ways founders can improve their elevator pitch by focusing on six key successors, the rules for understanding another’s perspective, and five frames to clarify your message and optimize it for persuasion.

Pitch Anything - Oren Klaff

When it comes to pitching, startup founders can learn a lot from Oren Klaff, the Director of Capital Markets for the investment bank Intersection Capital.

Klaff outlines his STRONG method, a formula he has used to raise over $400 million for his firm:

  • Setting the Frame

  • Telling the Story

  • Revealing the Intrigue

  • Offering the Prize

  • Nailing the Hookpoint

  • Getting a Decision

Final Thoughts

A common theme throughout this list is learning lessons from the legends who have invested years and millions of dollars to optimize their sales process. Each startup is unique and there is no single perfectly tailored blueprint for success, but the mindset for success and willingness to explore creative solutions gained from these books can be an excellent guide.