9 Must-Reads to be a Rockstar Salesperson

Salespeople tend to be doers. Usually, we’d rather get out there, sell, learn from the market, and go from there. We don’t tend to be particularly academic about our trade. I didn’t think to read a book on sales for years; I was too busy doing the thing to learn about how to do the thing better. But when I did, it was the single most transformative event in my sales career, and literally turned my business around (story below). To spread that wealth, we’ve collected the top sales book recommendations from our favorite sales-folk in Boston, Chicago, and New York. Technically, some of them aren’t even sales books, but they can have massive impacts on how you talk with your customers and close more business (hint: mine’s one of them).

Here are our top nine (plus one bonus) recommendations for the modern high-growth salesperson:[bctt tweet="9 must-reads for high-growth salespeople, by @ShorterThanRich"]

Give and Take by Adam Grant

inspiration for your sales career
inspiration for your sales career

Recommended by: Katya Siddall

  • Director of Business Development at CardConnect
  • Startup Institute Chicago Instructor

Katya's takeaway:

I recommend and re-read this book regularly. I think it’s powerful because it emphasizes two main points:

Being a good person who helps others is actually a major asset to long-term success and a key to a solid network. This is especially important if your company is starting out and doesn’t have inherent street cred.

Helping others doesn’t mean exhausting your resources or not protecting your work time.

The people that I’ve connected with the most in business (and really respect as mentors) have all read this book, and it often creates an instant bond when we realize we both have read it. I sell through relationship-building, and it really helps validate that approach![bctt tweet="Helping others is key to long-term success in sales, says @KatyaSiddall"]

Also recommended by: Craig Wortmann

Craig's takeaway:

I’ve given away tons of copies of this book (I may be Adam’s best customer). For my students, entrepreneurs, and sales professionals, it shows us that “givers” (people who seek to help others by making connections, by adding some small value in some way, and by having a long-term view of relationships) are the ones who succeed in the long-run. I love that. Adam has all of the research chops, so it’s credible, but it’s also easy to read and FULL of insights into networking, sales, and life.[bctt tweet="bctt tweet="Whether you're an entrepreneur or a sales professional, it's the givers who succeed @craigwortmann"]

Rework by Jason Freid and David Heinemeier Hansson

books to inspire your sales career
books to inspire your sales career

Recommended by: Chris Rohland

  • Consultant at Rohland Group Consulting
  • Startup Institute Boston Instructor

Chris' takeaway:

Written by the founders of 37Signals and Basecamp and geared towards entrepreneurs and startup founders/team members, this is a good read based on real experiences that challenge the status quo both at established organizations and even startups. It advises you on ways to do more with less, which we all know is great for startup companies.

My top takeaway from this book is how important it is to put yourself into your product or service. Competitors can copy what you do or sell, but they can’t copy the “you” in your product.

Rework isn't specifically a sales book. But it is certainly applicable to a career in sales, as well as to anyone else that wants to stop talking about doing things and just go do them.[bctt tweet="Competitors can't copy the YOU in your product, says @crohland"]

The Challenger Sale: Taking Control of the Customer Conversation by Matthew Dixon and Brent Adamson

book to help customer conversion at startups
book to help customer conversion at startups

Recommended by: Ryan Kurt

Ryan's takeaway:

Dixon and Adamson make a clear argument for how and why the rules of selling have shifted dramatically from when “old school” sales methods were created. It describes how a very specific sales approach outperforms the rest, combining an understanding of the “new” rules of how companies buy solutions and adjusting their behavior and activity accordingly.

(Ryan also shared his runner-up: SPIN Selling by Neil Rackham)

Also recommended by: Kevin Baumgart

  • VP of Sales at Hireology
  • Startup Institute Chicago Instructor

Kevin's takeaway:

The Challenger Sale outlines a way to teach, tailor and take control of sales conversations. It's no longer enough to have people "like you" and to be a "relationship" seller. You must be an expert in what you are providing and teach them something they don't know about how you can help them.[bctt tweet="It's no longer enough to be a relationship-seller-- you need to add value, says @BaumgartKevin"]

Predictably Irrational by Dan Ariely

book to learn how to sell
book to learn how to sell

Recommended by: Bob Greenlees

  • Director of Operations and Business Development at ShuttleCloud
  • Startup Institute NYC instructor

Bob's takeaway:

The essence of a sales career is understanding the perspective and motivations of the person with whom you are speaking and then positioning something in a way that leads to a desired result from your audience. There are lots of great books on sales techniques, but this book has continually proved the most useful in every sale, deal, negotiation, etc. The book investigates topics like the psychology behind pricing that can be applied to both how to price and sell SaaS products and how to position and negotiate large enterprise contracts. It is universally applicable and useful for everyone, but particularly for the sales professional.[bctt tweet="The essence of sales= understanding a perspective + positioning for a desired result @bobgreenlees"]

The Advanced Selling Podcast

Recommended by: Andy Cole

Andy's takeaway:

Since I don't take the time to read books as much as I have my ear buds in, I'd like to bend the rules a little and recommend a podcast. The Advanced Selling Podcast is about the mentality of the sales person.

I've found that having a mindset of "abundance" and "detachment" during the sales process has really influenced buyers and pushed my game to the next level.

For an example of "abundance," a salesperson must be confident that there are more than enough prospects out there-- that there are numerous potential clients out there that need and want your solution. This pressure-releasing attitude goes hand-in-hand with "detachment." We (especially type A, control-freaks like me!) tend to think about our wants, needs, quotas, etc. "I WANT to prove myself to my colleagues", "I NEED this sale", "I really NEED this commission." These are demonstrations of the wrong attitude, and they attach us to a given sale. A salesperson must have good intent: an attitude where you are putting your customer's needs in front of your own. In order to do this, you need to become aware of your wants and needs, compartmentalize them, and them behind the customer's needs, realizing that it's okay for a prospect to reject the sale (though, it's not okay for them to reject due to misinformation or poor sales process, but that's for another conversation!).[bctt tweet="A good sales representative will compartmentalize their own needs behind their client's @andypatcole"]

Predictable Revenue by Aaron Ross

insights for a sales career
insights for a sales career

Recommended by: Kevin Baumgart

  • VP of Sales at Hireology
  • Startup Institute Chicago Instructor

Kevin's takeaway:

Cold calling sucks. This book helps you warm it up. It also provides simple email templates to help initiate conversations.[bctt tweet="Predictable Revenue is a great read for warming up to cold calls @BaumgartKevin"]

Zero to One: Notes on Startups, or How to Build the Future by Peter Thiel

book that helps to build your sales career
book that helps to build your sales career

Recommended by: Jake Dunlap

  • CEO at Skaled
  • Startup Institute NYC Instructor

Jake's takeaway:

My biggest takeaway is the idea of the dead zone. This is the concept that products that sell from a price-point between a few thousand dollars and ten thousand dollars fall in a no man's land between sales and marketing in terms of who should drive the sale.

At that price point, it's difficult  to justify having full time sales people dedicated to selling as the margins are slim and it's also difficult for marketing to drive self service as the price point is slightly too high. It's a weird in-between that makes it difficult to know the best strategy to scale.[bctt tweet="The dead zone creates a no-man's land b/w sales + marketing. Who should drive the sale? @JakeTDunlap"]

The 4-Hour Workweek by Timothy Ferriss

book to inspire a more productive career as a sales representative
book to inspire a more productive career as a sales representative

Recommended by: Ransom Cook

  • Marketing Specialist at ThriveHive
  • Startup Institute Boston alumnus

Ransom's takeaway:

I just finished The 4-Hour Workweek recently and I found it so helpful in refining my sales process. There are so many good tips in there that are actionable for sales-people in staying effective in their day-to-day. It shows you how to strip down the distractions and go after the leads you need to so you can hit your quota month-after-month. Additionally, it provides information on working smart versus working hard, which I think is half the battle in becoming a successful sales representative. I would recommend The 4-Hour Workweek to sales reps who have gotten their legs under them and are looking for ways to optimize.[bctt tweet="Working smart- not hard- is half the battle as a sales rep, says @JRansomCook"]

The Lean Startup by Eric Ries

book to inform a startup sales career
book to inform a startup sales career

Recommended by: Rich DiTieri(aka yours truly)

  • Associate Director at Startup Institute Boston
  • Co-Founder at Pintley

My takeaway:

It’s no secret that I love Lean methodology. I talk about it pretty much any time I tell Pintley’s founding story (hint: near-failure, rescued by Lean). Even though it’s not a sales book, for me, there’s been no better application of Lean techniques than in all of my biz dev and sales career since reading it. It’s especially relevant for anyone selling a newly developed product or service, or selling to a new market where there’s no roadmap to follow. Or if you’re just trying to be a better sales-human. So, pretty much everyone.

The big lesson learned here is that if you treat your sales pitch or strategy as the product you’re developing, you can use the clearly laid out Lean tactics as a guide to build a great pitch.

Use simple frequent experiments to test, measure, and optimize sales techniques. It comes with the bonus of helping the rest of your team identify market trends, measure the reaction to the product in more than just the raw sales numbers, and it reminds you to make decisions using more than just your gut. Suddenly you’re not just out-selling your numbers, you’re preventing expensive mistakes and saving the dev team time. Go you.

TL;DR: If you’re new to a sales or account management job, or if you’re selling in unfamiliar waters...


  1. Read this book.
  2. Apply the “assume you know nothing,” “get to know your customers,” and “build-measure-learn” principles to develop your pitch and sales strategy.
  3. ???
  4. Profit!!![bctt tweet="Use Lean to out-sell your numbers, prevent expensive mistakes, + save time @ShorterThanRich"]

Bam. There you have it, folks. We salespeople may not be known for being bookworms, but we certainly are opportunists. Any of these options represent great opportunities to stretch yourself as a sales professional and refine your biz dev practices. Do you have other great book recommendations for a career in sales? Please share in the comments below.

Interested in building your sales career? Our sales & account management track helps individuals to build the confidence and capabilities to be high-impact in a sales role at a high-growth company. Download your free course guide, below.