The new VP Sales has the opportunity and responsibility to achieve aggressive growth targets, and make a deep impact on company-wide culture. That’s why we’ve hand-picked these 25 sales books (in no particular order) from the best in the field and organized them into the 5 key responsibilities of the new sales executive:
- Lead a team of top performers
- Craft a sales strategy that scales company revenue
- Hone team sales tactics
- Collaborate with cross-functional executives
- Land bigger sales at bigger companies (and sell to the C-suite)
Lead a team of top performers
VP Sales become VPs because of their successful track record – ususally as a rep and manager. But as an executive, their role is to scale their talents with a team that will achieve their sales targets year-over-year. These books teach basic and advanced management strategies to lead top-performing sales teams.
The Straight Truth About Getting Exceptional Results from Your Sales Team
by Mike Weinberg (2015)
This book tops our list for the new VP Sales because it encourages leaders to take full responsibility for the performance of their sales teams, gives no-nonsense tips for world-class sales management, and roots it all in real-life stories.
As a consultant, Mike Weinberg has seen many sales organizations that struggle under executives and sales managers that unknowingly undermine performance. “I was tired of being called into companies by senior executives to fix their ‘sales problems,’ only to discover that it was a leadership problem,” Weinberg explains in an interview with the CEO of Peak Sales Recruiting, Eliot Burdett. “If it’s broken at the top then it’s broken and the team will never do better than the leader.”
Readers will learn the 16 basic sales management flaws and how to create a healthy culture in their sales organization, match high performers with the right roles and coach underperformers, run meetings their teams actually look forward to, and structure the best compensation plan. “Long on solutions and short on platitudes,” Weinberg’s guide for sales executives is a must-read.
Build Repeatable Pipeline and Accelerate Growth with Inside Sales
by Trish Bertuzzi (2016)
Jill Konrath calls Bertuzzi’s book “the Sales Development Bible.” This book’s focus on teambuilding and recruiting makes it particularly useful for sales executives who need to scale their sales teams, recruit with urgency, and get deep and practical advice on retention through engaging, motivating, and developing their best talent. Also helpful is its strategic guidance on building new pipeline for your specific market. This is a highly actionable, step-by-step guide divided into 6 sections.
The Sales Managers’ Success Guide
by Steven Rosen (2012)
52 Sales Management Tips presents 52 concise and clear-cut tips for the sales executive who’s strapped for time yet knows they need to develop their team. It’s an easy read at a short 60 pages, and the tips are bite-sized and standalone, so readers can pick it up and read in small pieces here and there, rather than all in one go (one tip a week for a 52-year week).
“Wow, Steven has got it right…Focus on sales management to increase sales performance. No complicated strategy, just actionable coaching tidbits that guide you to the right tool for the right situation at the right time.” — William “Skip” Miller, author, ProActive Sales Management
by Ken Thoreson (2011)
Ken Thoreson of Acumen Management provides a practical guide to managing sales teams, with hundreds of specific tactics and techniques a new VP Sales can experiment with immediately.
This book is easy to digest because it is broken into 39 chapters. Readers will learn:
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- How to Build a High-performance Sales Culture
- How to Make Monday Morning Sales Meetings Count
- Why Leadership Matters
- How to Create Your Own Sales Certification Plans
- How to Develop Sales Compensation Plans that Work
- How to Lead Sales Contests that Increase Sales and Build Teamwork
- How to Measure and Manage Sales Activity
- How to Uncover Leading Indicators that Predict Revenue
- How to Build a Self-managed Sales Team
- Time Management Techniques for Sales Managers
A Tactical Playbook for Managers and Executives
by Keith Rosen (2008)
Keith Rosen argues that sales executives need to focus on coaching, not sales training, in order to develop a team of high performers in the cutthroat sales environment. This sales coaching handbook teaches how to create a thriving internal coaching program, and broader culture where coaching is woven into everyday activity. It teaches how to recognize the different management styles you’ve encountered in your sales career and how to steer your own style away from a tyrannical one to a coaching-oriented one.
This book is a winner of five International Best Book awards. It provides immediately actionable tips on how to coach anyone in any situation, This book fights general advice and platitudes by providing proven coaching scripts, questions, and templates, as well as real-life stories and deep dives into mistakes coaches make. It even offers a 30-day intervention strategy to turn around poor performers.
by Jill Konrath (2014)
The only constant in the sales world is change, and this book helps the new Sales VP assimilate into their management role quickly. It’s also widely applicable framework for their own reps to get up to speed in new situations, like pivots, promotions, and industry changes. The no-nonsense book presents “meta-skills” to quickly absorb tons of information, ramp up on new skills nearly overnight, manage a busy calendar, keep motivation high, and gamify sales work. Readers will carry these habits throughout their careers and benefit long after they finish the last chapter.
Craft a sales strategy that scales company revenue
A new VP Sales’ role in a start-up is to bring a company from initial traction to initial scale. Strategy is a core responsibility, and once a company reaches ~$20m ARR, the VP Sales should shift focus away from tactics even more to go deeper into strategy – Jason Lemkin.
Using Data, Technology, and Inbound Selling to Go from $0 to $100 Million
by Mark Roberge (2015)
An engineer from MIT, Mark Roberge took HubSpot’s sales through the company’s first 10,000 customers. He pioneered a new method of scaling sales through metrics, process, and inbound selling. Roberge argues that sales can be taught; that there is a science and process behind it that one can distill into a replicable formula. This book is that formula, teaching readers a practical approach to bringing prospects from lead gen to sales in a combined sales and inbound marketing collaboration. “Readers will learn how to apply data, technology, and inbound selling to every aspect of accelerating sales, including hiring, training, managing, and generating demand.”
Inbound content and lead generation has changed the sales landscape, and it’s here to stay, so it’s an especially important read for the contemporary VP Sales. Roberge covers five key areas — four formulas and a way to think about technology in the sales context.
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- Hire the same successful salesperson every time — The Sales Hiring Formula
- Train every salesperson in the same manner — The Sales Training Formula
- Hold salespeople accountable to the same sales process — The Sales Management Formula
- Provide salespeople with the same quality and quantity of leads every month — The Demand Generation Formula
- Leverage technology to enable better buying for customers and faster selling for salespeople
12 Proven Strategies for a Customer-Driven World
by Steve Andersen and Dave Stein (2016)
Steve Andersen and Dave Stein argue that sales professionals who focus on just getting the sale are making a fatal mistake: what one does before and after the sale is just as important. The average executive spends less than 5 percent of their time engaged in the buying of products and services, so sales teams need to make sure they’re engaging these executives the rest of the time as well. This book divides 12 strategies into three sections: how to drive success before the sale, during the sale, and after the sale. It teaches how to create value for customers at all times and not just being reactive to requirements in an RFP. The book is backed by research and illustrated with case studies from companies like Hilton and Siemens, making it one of the most captivating sales books of 2016 and one we recommend all emerging sales leaders read.
“Most sales books assume that only the sale matters. Not true. This book considers the whole picture—what’s happening when your customers aren’t buying from you influences them when they are.” — Yvonne Genovese, GVP, Gartner, Inc.
Winning Moves for Growing Companies
by Paul O’Dea (2009)
This book is a field guide to sales strategy for senior executives of growing companies. The Business Battlecard helps the reader “craft a winning strategy that will win you the war on several fronts: the battle against competitors, the battle for customers’ minds, the battle for investors’ wallets, and the battle for employees’ hearts.” It covers how to devise a clear strategy, align the team, align other executives, and execute. The book includes a one-page visual summary (a “battlecard”) for what you need to focus on and guides the reader through five key questions.
The Unique Sales System Proven Successful by the World’s Best Companies
by Robert Miller and Stephen Heiman (2008)
The Miller Heiman sales strategy and the classic book Strategic Selling became a cornerstone for salespeople and non-sales businesspeople alike with the introduction of the “Win-Win” concept in 1985. The authors revised the book in 2008 for modern complex sales, covering strategic topics like creating steady revenue (avoiding boom and bust), understanding competitive offerings and substitutes, identifying the four real decision makers in even the most vexing corporations, and closing the right business, not business you’ll regret later.
Powerful Strategies to Drive Consistent Growth Year After Year
by Colleen Francis (2014)
This book teaches sales executives how to avoid boom-bust cycles and create a sales system to smooth out erratic highs and lows each quarter. Francis introduces the Sales Radar concept, which is a holistic way to characterize prospects alongside the sales funnel. This is divided into four sections which she argues each deserve attention and work in harmony to create a steady supply of wins throughout the year: Attraction (filling the pipeline), Participation (turning leads into customers), Growth (picking the best clients and investing in them), and Leverage (generating referrals). Peak Sales Recruiting reviewed this book in depth because of its standout concepts for long-term business growth.
“Packed with enlightening examples of sales disasters and standouts…brings balance to the selling process, reliability to revenues and booming sales all year long.” — Top Sales World
Hone team sales tactics
A new Sales VP needs to scale their work with a high-performing team, implementing advanced sales tactics. And from time to time, their responsibility is to close sales themselves — something taking a deal from end to end. These hand-picked books will expand the reader’s tactical skill to deal with any situation.
Surprising Research on What Sales Winners Do Differently
by Mike Schultz & John Doerr (2014)
This book helps B2B sales teams adapt to the new paradigm, in which, the authors argue, buyers see products and services as replaceable. Schultz and Doerr interviewed over 700 B2B purchases and found that the #1 winners sold radically differently than the #2 finishers. They share their new data, as well as a three-level Insight Selling model that helps sales executives parse out which advice to follow, which to discard, and what parts of their existing processes aren’t working anymore. This is an important read for the new VP Sales and for members of their team.
“Schultz and Doerr are truly among the elite sales thought leaders. Insight Selling outlines exactly what you need to do to set yourself apart and find yourself in the winner’s circle. It’s a must read for even the most experienced sellers.” — Jill Konrath, bestselling author of Agile Selling & SNAP Selling
The Sales Professional’s Guide to Improving Customer Profits
by Jack Malcolm (2011)
Jack Malcolm’s philosophy to selling focuses on the bottom line — of your customer. This book helps the new VP Sales and their team navigate their prospects’ business goals and problems to cultivate a deep understanding that leads to value creation. “The only way to add measurable value to your customers—the kind that gets the attention of high-level decision makers—is to understand how their business generates cash, bring solid ideas for improving their cash flow engine, and speak the language that resonates with them,” says Malcolm.
“I read a lot of business books, more than 100 a year, and I can say without question that Bottom-Line Selling is absolutely one of my all time favorites. If you want to clearly understand how to use business acumen, competitive intelligence and your customer’s financials to position yourself as a trusted advisor and close major deals, this is a MUST read book.”— John Spence
The Ultimate Guide to Opening Sales Conversations and Filling the Pipeline by Leveraging Social Selling, Telephone, Email, Text, and Cold Calling
by Jeb Blount (2015)
A key responsibility of the VP Sales is to inspect pipeline and make sure it’s being filled in a healthy, sustainable way. This book is a well-loved, must-read basic guide to prospecting that’s well worth a revisit for leadership hoping to train their team to improve lead generation.
“Jeb Blount turns the most despised activity in sales – PROSPECTING – upside down. He nails it with his insights, humor, and expertise, making this a book every salesperson, entrepreneur, and executive must read. Get ready to come away with more strategies and ideas and you’ve ever found in one place.” — Mark Hunter “The Sales Hunter” author of High-Profit Selling: Win the Sale Without Compromising on Price
How to use the magic of metaphors to sell, persuade & explain anything to anyone
by Anne Miller (2009)
Some of the best sales executives infuse their sales tactics with metaphors (and teach their teams how to call on metaphors for better selling). This is particularly important for companies selling visionary solutions or complex technologies that are difficult to articulate, as well as to cut through the noise of content overload online. In four steps, this book teaches readers how to “weave the magic of metaphor into your business arguments to sell an idea, clear up confusion, shake up indifference, close a sale, vaporize objections, wow an audience, inspire action and make your point.” This is an entertaining read, with over 250 real-world examples, opening with the “Sorry Seven” — the seven types of speakers who put even the most willing listeners to sleep.
“Metaphors are communication home runs. This book shows you how to hit them.”— CHICAGO TRIBUNE
How to Master the RFP System Once and for All to Win Big Business
by Tom Searcy (2009)
In industries where RFPs are a required component of dealflow, new sales executives should read this book for ideal strategies and tactics to contend with the RFP world. It teaches how to navigate the time-consuming, expensive, and often unfairly balanced RFP process — as well as advice on when to quit or to double down and win the deal.
“This is the first book I’ve seen on this grossly overlooked topic and it’s definitely a winner. Smaller firms hoping to land large corporate customers will find the most value, but even sellers from big companies will learn new tricks. In short, you’ll discover how to qualify, divide and conquer RFPs that make the most sense for your company.”— Jill Konrath, Author, Selling to Big Companies
by Jack Malcolm (2012)
Presentations to senior decision makers are high stakes: sales teams have a clear shot to win, but if they fail, they’ll be sent home quickly. Malcolm presents an end-to-end guide for creating and delivering world-class pitch presentations to high-level prospects. It covers with planning and positioning, presentation crafting, and delivery for 30- to 60-minute pitches.
“This book will transform any salesperson into a strategic salesperson and the more strategic you are, the higher value you sell.” — Nancy Duarte, CEO, Duarte, Inc. award winning author of slide:ology and Resonate
by Dan McDade (2011)
A successful VP Sales knows how to work closely with the heads of marketing and demand generation in their company to create a full pipeline of highly qualified leads. Dan McDade, CEO of PointClear, provides a guide to excellent B2B lead generation. The Truth About Leads a must-read for sales executives who are new to the lead generation world or want to solidify their foundation to prospect development as they scale their business.
The Choices, Systems, and Behaviors that Drive Effective Selling
by Frank Cespedes (2014)
Harvard Business School professor Frank Cespedes helps executives close the gap between its strategy and sales efforts. The book provides new research, examples, and an actionable framework to show how sales fits in the broader context of the rest of the business and how it affects value creation for the customer.
“Frank Cespedes has brilliantly captured why aligning strategy and sales is so darn difficult. He walks you through the alignment process in a methodical yet witty manner, reminding you of the nitty-gritty intricacies that will provide the wind in the sails of your strategy. This book should be required reading for all senior executives and sales managers.” — Jeanne O’Kelley, cofounder and CEO, Blueprint Technologies
The Secret Weapon That Can Solve Your Toughest Sales Challenges
by Tim Sanders (2016)
Tim Sanders argues that “sales genius is a team sport,” and puts forth a structured, scalable, and repeatable brainstorming-type process called “Dealstorming” to problem-solve complex sales deadlocks. It involves everyone who touches a sale (especially those outside of sales teams) and taps into the team’s wisdom and creativity to generate truly innovative ideas, with success at companies like Yahoo! and Condé Nast. This recent release is a good read for a VP Sales who needs to get a lucrative and complex deal unstuck by collaborating with cross-functional teammates.
by Dale Carnegie (1937 original, 2016 new edition)
We all saw this one coming. How to Win Friends and Influence People is a 1937 classic that remains one of the most widely-read self-help books in the world. It takes on new meaning for a VP Sales, who now has to collaborate with a new set of executive counterparts in marketing, product, and engineering (and has to manage people — who might have once been their peers, in the case of an internal promotion). The publishers recently released a new edition with some updates; the core of the book remains applicable to this day.
“It changed my life.” — Warren Buffet
Land bigger sales at bigger companies (and sell to the C-suite)
These are must-reads for the VP Sales whose company’s growth strategy includes closing larger deals with larger companies.
by Jill Konrath (2012)
Jill Konrath focuses on how to get your foot in the door with larger enterprises in “Selling to Big Companies.” It covers how to target the prospects where sales teams have the highest chances of success, find the right names, get a meeting with a corporate decision maker, create value propositions that catch their eye, and more. This book is one of Fortune Magazine’s 8 must-read sales books and a Gold 
Medal Winner of the Sales Book Awards.
“This book takes the mystery out of selling to these corporate behemoths. Read it to shorten your sales cycle and avoid the many traps that can derail your sales efforts.”—Gerhard Gschwandtner, Founder and Publisher, Selling Power
How to Land Big Sales and Transform Your Company
by Tom Searcy & Barbara Smith (2008)
This book is for the VP Sales who plans to grow their business by going after larger enterprises and contracts. As the authors put it, “Stop wasting time with little accounts and start landing monster accounts.” While many books focus on the individual salesperson, this one focuses on collaboration and teamwork. It provides a nine-step method to find and land big deals, and is particularly useful for answering higher-tier RFPs. (No whales were harmed in the writing of this book.)
What You Need to Know to Sell Successfully to Top Executives
by Michael Nick (2011)
Author Michael Nick argues that as budgets tighten, purchasing decisions land in the hands of the C-suite — and that sales teams need speak their language. This requires gathering a specific type of advance intel and crystallizing the value proposition in a way that high-level decision makers can understand. It is more practical and tactical than most, teaching how to:
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- Find key financial information on a prospect
- Determine a corporation’s financial stability
- Clearly define the value of the product or service they are selling
- Calculate the value impact of their offerings in financial metrics
- Clarifying how sales packages fit into metrics such as return on asset, return on equity, operating costs, net profit, and earnings
What Every Executive Wants You to Know About Successfully Selling to the Top
by Dr. Stephen J. Bistritz and Nicholas A.C. Read (2009)
With 60 years of combined experience selling to corporations around the world, the authors conducted in-depth interviews with executive-level decision makers of more than 500 companies and government organizations to provide concepts and strategies that have been proven through repeated application. They demystify the executive’s role in the buying process — when they step in, and how they affect the deal. They cover how to gain access to executives, establish trust, and create value that resonates at the C-suite.
“If you’ve been in the sales business for a while, you’ll remember Steve’s fine work at Target Marketing Systems. This book really gets to the heart of the matter. With no quick fixes or silver bullets, this book is serious about getting you into the C-Suite and keeping you there.” — Dave Stein, Sales Hiring Expert and author of “Beyond the Sales Process”
We hope you enjoy this reading list. Please leave a comment below with a book that has changed the way you think about your approach to sales, management, and helping your customers.
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ay B2B selling is both conducted and understood. The market research company Marketo notes that 93% of consumers, both B2B and B2C (business-to-consumer), begin their purchase journey online. This should matter to Millennials because it positions this generation as potential workforce leaders because they use and understand technology with more proficiency than any generation before. In fact, David Goldin, founder and CEO of Capify, explains that “millennials are actually the most creative, entrepreneurial, and technologically savvy of all in the workforce.” A far cry from the lazy and entitled labels that often follow Millennials around, Millennials actually hold a leadership position in the workforce as a whole in terms of how they utilize and harness the disruptive power of technology.
ompetitiveness Project notes that one cloud based software company missed out on $2 million in annual revenue due to a failure to bring on enough sales personnel to get their product to market. Simply put, this means there is an abundance of opportunity to work in these sectors. Competition is high but the market is only expanding, which means there are opportunities if you seek them out.
nals, is a significant part of attracting the best sales talent.
