Books › Best Sales Books
Best sales books for software and B2B sellers
Most sales reading lists mix every kind of selling together. This one is for people selling business software, from the first outbound calls to enterprise deals and team leadership, and it is ordered by where you are in the job.
Each book is here for a reason: the notes say what it covers, where it fits in a sales career and when it is worth reading.
Getting started
SPIN Selling
by Neil Rackham · 1988
~200 pages~5 hrs to read
Built on research into large B2B sales calls, it teaches the Situation, Problem, Implication and Need-payoff question sequence. A strong base for running discovery before you pitch.
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Fanatical Prospecting
by Jeb Blount · 2015
~290 pages~7 hrs to read
Covers prospecting cadence, phone, email and social outreach, and protecting daily time for pipeline work. Useful when part of your pipeline is yours to source.
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Predictable Revenue
by Aaron Ross, Marylou Tyler · 2011
Describes the outbound model that separates prospecting from closing, including dedicated lead-generation roles. Read early to understand why sales development exists and how it feeds the sales team.
View book →New Sales. Simplified.
by Mike Weinberg · 2012
~240 pages~6 hrs to read
A short, practical guide to prospecting messages, first meetings and a sales story built around the buyer's problems. Good for restarting a thin pipeline.
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Doing the job
The Challenger Sale
by Matthew Dixon, Brent Adamson · 2011
~220 pages~6 hrs to read
Draws on rep-performance research to describe teaching, tailoring and taking control of the conversation. Read it when moving from relationship selling to leading customers with insight.
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Gap Selling
by Keenan · 2018
~260 pages~7 hrs to read
Frames selling as diagnosing the gap between a buyer's current and desired state, then quantifying the cost of the problem. Helps with weak discovery and stalled deals.
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The JOLT Effect
by Matthew Dixon, Ted McKenna · 2022
~260 pages~7 hrs to read
Looks at buyer indecision, a main reason deals stall, and how to read it and move customers forward. Practical when your forecast is full of no-decision outcomes.
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Never Split the Difference
by Chris Voss, Tahl Raz · 2016
~290 pages~7 hrs to read
A former FBI hostage negotiator explains calibrated questions, labeling and tactical empathy. Applies to pricing, procurement pushback and late-stage discount requests.
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Getting to Yes
by Roger Fisher, William Ury, Bruce Patton · 1981
~200 pages~5 hrs to read
The Harvard negotiation method: separate people from problems, focus on interests, and invent options. A useful counterweight to price haggling in contract and procurement talks.
View book →Objections
by Jeb Blount · 2018
~240 pages~6 hrs to read
A step-by-step approach to brush-offs, stalls and objections on calls. Read it once you hear the same pushback every day and want a repeatable response instead of improvising.
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Great Demo!
by Peter E. Cohan · 2005
~310 pages~8 hrs to read
Sets out a method for software demos built on discovery first and showing solutions to stated problems. Worth reading before you run your own demos or work alongside a sales engineer.
View book →Rejection Proof
by Jia Jiang · 2015
~230 pages~6 hrs to read
Jiang's account of seeking out rejection for 100 days to lose his fear of it. Speaks to the resilience cold outreach demands; useful when a run of no's starts wearing on you.
View book →The Sales Development Playbook
by Trish Bertuzzi · 2016
A practical look at how sales development teams are built and run, from process to metrics. Shows the system around a prospecting role and what a well-run team expects.
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Senior and leading
The New Strategic Selling
by Robert B. Miller, Stephen E. Heiman, Tad Tuleja · 1985
~430 pages~11 hrs to read
A framework for mapping the buying influences, competitive position and red flags in a complex account. Suited to enterprise deals with several stakeholders and long cycles.
View book →The Sales Acceleration Formula
by Mark Roberge · 2015
~200 pages~5 hrs to read
Roberge, a former HubSpot sales leader, lays out a data-driven approach to hiring, training and managing sales reps. For people stepping up to team lead or first-line management.
View book →From Impossible to Inevitable
by Aaron Ross, Jason Lemkin · 2016
~320 pages~8 hrs to read
Covers how SaaS companies scale revenue past the early stage, including the outbound pipeline engine. For sales leaders thinking about pipeline at company scale.
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Reading for a specific role?
Each of these roles has its own books page, with the books that matter most for that job.
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