Spring break means vacation – and vacation means plenty of down time to catch up on reading! So order the margarita, stroll down to the beach, and grab a book for a little beach reading. What will it be?

We assume you have an old copy of How to Win Friends and Influence People in your bookcase, and certainly Dale Carnegie’s book is a must-read for anyone in customer-facing roles. But a.) it’s not beach reading, and b.) it’s almost 100 years old!

We have mad respect for the classics – but we’ve updated the sales reading list for 2019.

Start fresh on vacation with this curated list of new, diverse, must-read books – especially for salespeople who sell SaaS and other cloud-based products.

Outbound Sales, No Fluff – by Rex Biberston and Ryan Reisert

best sales books 2019 for saas sales The full title of this book is the first baller move of many: Outbound Sales, No Fluff, Written By Two Millenials Who Have Actually Sold Something This Decade. (This alone may set this book apart from a lot of other sales dev books by some sales training professionals.)


Nobody cares about your product. That’s the first lesson. Other lessons include straight talk about cold calling, funnel math, segmentation, and sales tech.

For Millennials, who came of age in the era of cloud technology, SaaS is no big deal. But for buyers who may not be as comfortable or familiar with a cloud-based environment, sales skills and SaaS knowledge are a perfect combination.

Watch it: 8 TED Talks All Salespeople Must Watch

Agile Selling – by Jill Konrath

best sales books 2019 to read on spring breakAgility is a critical skill for modern sellers: Cloud-based products are constantly evolving, the pain points and buyers are changing.


This is the norm when selling in a SaaS world. There’s a lot of money to be made. But to get a slice of that pie, sales professionals must change too.

This is the heart of Agile Selling: Getting Up to Speed Quickly in Today’s Ever-Changing Sales World, by Jill Konrath.

“I was struck with a realization,” Konrath says. “There were so many factors, beyond sales skills, that contributed to my success – like how I deal with fear, my never-fail mindset, and thinking from my customer’s perspective. …I realized that my abilities to get up to speed quickly and rapidly adapt to changing conditions were what mattered most.”


Adapting to change is key. Whether it’s cloud-based products evolving to new needs and new markets, salespeople adapting to new sales technologies, or products so cutting-edge that you can barely describe them – don’t get comfortable. Get agile.

The Sales Acceleration Formula – by Mark Roberge

2019 best sales books for cloud-based Saas sellersYes, the author has actually built a $100 million business himself – a little company called Hubspot. And no, the MIT-trained engineer did not have a business background.


Roberge had no experience in “scalable, predictable revenue growth” (…the business mantra. Sound familiar?). And yet the engineer was able to do something that a lot of sales leaders could not: Break down the big picture into logical, scalable parts that could be analyzed and replicated.

The Sales Acceleration Formula: Using Data, Technology, and Inbound Selling to go From $0 to $100 Million by Mark Roberge tells the story of how two very different skill sets, each with a lot of prejudice toward each other – are actually the perfect modern pairing in SaaS sales.

Listen: [PODCAST] The Road to $100 Million with Matt Wheeler

The Sales Development Playbook – by Trish Bertuzzi

best beach reading sales books 2019It’s easy (even helpful) to try and copy what other companies are doing successfully – “But it’s next to impossible to see why, how, and if that approach is appropriate for you.”


To “do” sales development, Bertuzzi says, it needs to be a dedicated role. The Sales Development Playbook identifies six parts to the role of sales development: strategy, specialization, recruiting, retention, execution, and leadership.

Put a focus on strategic growth by shining a light on sales development. (Good thing you’re on the beach; you might need an extra margarita for this one.)

The Hard Thing About Hard Things by Ben Horowitz

best sales books of 2019 to read on vacation beach spring breakWe were first attracted to this title because DiscoverOrg’s CEO, Henry Schuck, often talks about “doing the hard things.” Schuck and author Ben Horowitz are talking about the same thing:


“The hard thing isn’t setting a big, hairy audacious goal. The hard thing is laying people off when you miss the goal. The hard thing isn’t hiring great people. The hard thing is when those ‘great people’ develop a sense of entitlement and start demanding unreasonable things.”

In The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers, Horowitz goes on to describe several times in his life that were dictated by fear of the unknown, and misplaced assumptions. Each time, after he was able (or forced) to do the thing he feared, the hard part evaporated.

If you know you’re capable of great achievement but find yourself so paralyzed by uncertainty that you never get there – this book is for you.

The Tall Lady with the Iceberg by Anne Miller

best sales books of 2019 for salespeople to read on vacation If you think creativity can’t be measured in dollars, Anne Miller disagrees. The Tall Lady with the Iceberg is a great beach read for SaaS sellers: clever, logical, colorful – perfect for vacation!


When you’re trying to stand out in the crowded SaaS marketplace, features and benefits aren’t going to get buyer attention. But your approach – your language and storytelling in particular – can make you stand out.

But you know it’s not just about standing out.

When you’re selling cutting-edge software or other cloud products, there’s a good chance your product is unique, disruptive, and complicated. The Tall Lady With the Iceberg: The Power of Metaphor to Sell, Persuade & Explain Anything to Anyone is a great resource to help sales professionals use metaphor and imagery to sell something that’s hard to even describe.

On one hand, you’ll find logical, concise arguments that you can make your own – and Miller has the formula to implement them. On the other hand – icebergs!

Product Demos That Sell: How to Deliver Winning SaaS Demos by Steli Efti

best books for selling cloud tech saas You’ll be able to finish this book in the time it takes to build a good sandcastle, and it might be the best hour you spend all spring break.


You’ll learn best practices for scheduling demos, how to engage prospects and give killer demos, startup-specific demo tips, and of course, the 7 Deadly Sins of Demoing.

Product Demos That Sell by Close.io founder Steli Efti is based on the premise that nothing establishes credibility faster than showing prospects that your #1 concern is that the product is a good fit for them. (Emphasis: them.)

There are a lot of other great sales books out there, but you probably want to spend some time in the pool. So start here, and return to work relaxed, refreshed, and with a few new tricks up your sleeve.

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Charity Heller
About the author

Charity Heller

Content Strategist, DiscoverOrg

Charity Heller, DiscoverOrg's content strategy manager, has been developing, composing, and editing content since age 2. Before her dive into content marketing, she founded and operated a book-editing company for 10 years. Charity has a B.A. in English literature, Professional Editing Certification from U.C. Berkeley, and she's a certified Project Manager.