The Holloway Syllabus on B2B Sales

Published October 16, 2019

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Last update January 5, 2024

▪︎ 13 minutes read time

Introduction

Two salespeople may see exactly the same characteristics in a customer, but the successful one will spot the characteristic that matters above all others and establish a sales strategy accordingly.Philip Delves Broughton (The Art of the Sale)

This list required over 40 hours of research. Thank you to Tom Eisenmann from Harvard Business School to for curating many of these great resources (Tom credits Frank Cespedes at HBS for helping him). We believe this is the most comprehensive and authoritative list (over 100 resources!) to help you master the ins and outs of B2B sales.

Whether you’re a founder who needs to figure out how to make the business work, someone who thinks they might make a great salesperson, or an employee curious how the sales department affects the rest of the company, it can be a struggle just to get started. This list is an ideal place to bookmark and return to.

A lot of the resources in this syllabus focus on software sales, but the principles and concepts are relevant to folks who sell all kinds of things, from hardware to services.

B2B Sales 101

• What is B2B Sales? — Wendy Connick
• Do I need a B2B sales team?
  • If SaaS Products Sell Themselves, Why Do We Need Sales? — Mark Cranney
• Terminology
  • 101 B2B Sales Acronyms And Abbreviations, Defined — Bernie Reeder
  • Common Sales Terms Explained for Marketers — Lindsay Kolowich

Overview of the Sales Process

• Introduction to the Sales and Marketing Machine (Series) — David Skok
  • Building the Machine
  • Instrumenting the Machine
  • Solving Blockage Points
  • Refining the Process
  • How JBoss Rose to the Top
  • Get Found using Inbound Marketing
  • Focus and Market Segmentation
  • Where it all started: The One Day Sales Cycle
• Do you know your Customer? Buying Cycle & Triggers — David Skok
• What is the Buyer’s Journey and Why Should You Care? — Lina Vashurina

General Sales Tips

• The 39 Best Pieces of Sales Advice You’ll Hear This Year — Wiley Cerilli
• A Dozen Things I’ve Learned About Marketing, Distribution and Sales — Tren Griffin
• Peter Thiel’s CS183: Startup - Class 9 Notes Essay—If You Build It, Will They Come? — Blake Masters
• Do Things That Don’t Scale — Paul Graham

Sales Strategy

Getting Started

• Design Your Initial Product Offering to Attract Fortune 500 Enterprises — Deepak Kumar
• If You Have 10 Unaffiliated Customers in SaaS, You Have Something — Jason Lemkin
• Six Common Reasons SaaS Sales Plans Fail — Deva Hazarika
• Direct Sales for Bootstrapped SaaS Startups: from $1,300 to $725,000 MRR — Nathan Barry

How Sales Organizations Evolve

• 🔥 The Sales Learning Curve — Mark Leslie and Charles Holloway — Explains the three phases of any product and why different types of sales people sink or swim in each.
• The Peter Pan Syndrome–The Startup to Company Transition — Steve Blank — How sales culture must change as a company matures.
• For every stage, there is a salesperson — Joe Kraus
• From SMB to the Enterprise: When to Move Upmarket — Alex Niehenke

Choosing a Sales Model

• 🔥 SaaS Startup Strategy | Three SaaS Sales Models — Joel York
• How To Pick A Sales Model For Your Software Startup — John Doherty
• Sales Complexity is Destroying Your Startup’s Viability — Brian Zimmerman
• Software’s Valley of Death — Raj De Datta

Sales Methodologies

• The Sales Methodology Blueprint: How To Choose The Right One For Your Business — Jacco Van der Kooij
• Why Your Startup Needs a Sales Methodology (PUKKA) — Mark Suster
• Sales Leadership Lessons From 10 Years at HubSpot — Mark Roberge
• How Account Based Marketing is reinventing GTM — Tae Hea Nahm

Inside Sales

• ​slides​No Sale Left Behind: Sell More, Better, Faster With Inbound Sales — Brian Halligan
• Enterprise 2.0: The science of inside sales — Scott Irwin
• The Trend that is Changing Sales — Steve Martin

Channel Sales

• The Fallacy of Channels: Startups Beware — Mark Suster
• From Zero to 10,000 Customers in Two Years Using Channel Partners — Gabriel Weinberg

Scaling Sales

• Scaling Sales: From Craft to Machine — Jeff Bussgang
• Give Your Teams Swiss Army Knives — Mark Suster
• The Secret Weapon to Scaling: Sales Operations — Jeff Bussgang
• The SaaS Manifesto: Part Two—It’s Time to Build a Real Sales Team — Peter Levine

Managing Conflict with Sales and Other Functions

• Bonfire of the Vanities — Steve Blank — Managing the often contentious relationship between sales and marketing in startups.

Specific Sales Tactics

• Scaling Sales: Arming & Aiming—A’s, B’s & C’s — Mark Suster — Qualifying your pipeline by likeliness to close and prioritizing your time to focus on the best deals.
• How to Shorten Your Sales Cycle and Avoid Wasting Time — Mark Suster — The benefits of “calling high” vs. “calling low.”
• How to Sell Your Roadmap Without Selling Your Soul — Mark Suster
• The One Key Person That Will Help You Improve Sales — Mark Suster — Identifying and leveraging champions inside companies you’re selling to.
• Sales for Startups: Not All Leads Are Equal — Mark Birch — An examination of conversion rates for different sources of sales leads.
• When Selling is the Worst Way to Win Customers — David Skok — How building trusted sales relationships by adding value can lead to a sell much faster than a hard sell.
• At times not losing is as important as winning — Steve Blank — Challenges of closing a B2B sale with multiple decision influencers.
• Negotiating with Buyers — Mark Suster
• The Best Sales Reps Avoid “Talkers” — Brent Adamson, Matthew Dixon, and Nicholas Toman — How and why the best sales reps avoid those who superficially show enthusiasm but prove to be unable to mobilize support for a purchase.
• Meet the New Enterprise Customer, He’s a Lot Like the Old Enterprise Customer — Ben Horowitz
• Let’s Fire Our Customers — Steve Blank
• The Three Frameworks You Need to Kick-start Sales — Whitney Sales
• The Ultimate Cheat Sheet For Selling Anything — James Altucher
• Scaling Sales: Arming & Aiming—Objection Handling — Mark Suster
• Building Your Best Sales Deck Starts Here — Peter Kazanjy
• The Most Surefire Way I’ve Found to Win Enterprise Deals — Anand Chopra-McGowan
• This Sales Plan Moves the Needle on Every Success Metric — Derek Draper

Metrics

• Why Lead Velocity Rate is the Most Important Metric in SaaS — Jason Lemkin
• SaaS Metrics 2.0: A Guide to Measuring and Improving What Matters — David Skok
• SaaS Metrics 2.0: Detailed Definitions — David Skok
• The 3 Key Analyses For Measuring Your Startup’s Product Performance — Tom Tunguz
• Key Revenue Metrics for SaaS companies — Christoph Janz
• A KPI dashboard for early-stage SaaS startups — Christoph Janz
• Cold Call Ratios — David Cummings
• SaaS Inside Sales: What you need to know — David Skok — Includes a link to a Bridge Group report on metrics and compensation data for SaaS inside sales.

Sales Hiring

Hiring Sales Senior Management—Who and when to Hire

• 🔥 Don’t Hire a VP of Sales — Dave Hersh
• How to Hire Your First VP Sales and Not Screw It Up — Jason Lemkin
• The Types of VP Sales. Make Deadly Sure You Hire the Right One. — Jason Lemkin
• If Your VP Sales Isn’t Going to Work Out—You’ll Know in 30 Days — Jason Lemkin
• Should Your VP Sales Start Off as a Player-Coach? — Jason Lemkin
• What Has Changed in Sales? The Sales Manager — Bob Marsh
• Hire a Head of Sales — Peter Levine
• Managing a VP of Sales: It’s Not Supposed to be Easy — Scott Weiss

Hiring, Managing, and Motivating Sales Teams

• The Anatomy of the Perfect Sales Hiring Process — Peter Kazanjy
• Building an Enterprise Sales Team — Doug Leone
• Helping Startups Understand Salespeople & the Sales Culture — Mark Suster — What motivates sales people
• Through the Looking Glass: Hiring Sales People — Ben Horowitz
• When You Hire Your First Sales Rep—Just Make Sure You Hire Two — Jason Lemkin
• The ultimate sales hiring guide for B2B startup founders! — Steli Efti
• Some Thoughts about Selling at Startups — Mark Suster — When to hire sales people in an early-stage startup and how to choose them.
• Improving Sales: The Excuse Department is Closed — Mark Suster — Excuses offered by startup sales people.
• Building Startup Sales Teams: Tips For Founders — Dharmesh Shah
• The Science of Building a Scalable Sales Team — Mark Roberge — How to use analytics to build a scalable sales team
• Startup Sales—Why Hiring Seasoned Sales Reps May Not Work — Mark Suster
• The Best Ways to Hire Salespeople — Frank V. Cespedes and Daniel Weinfurter
• Hiring Your Startup’s First Salesperson — Tom Tunguz

Resources for B2B Sales

Books

• Books on sales for sales people
  • 🔥​book​Founding Sales: The Early Stage Go-To-Market Handbook — Peter Kazanjy
  • ​book​Secrets of Closing the Sale — Zig Ziglar
  • ​book​Aligning Strategy and Sales: The Choices, Systems, and Behaviors that Drive Effective Selling — Frank V. Cespedes
  • ​book​The Complete Guide to Accelerating Sales Force Performance — Andris A. Zoltners, Prabhakant Sinha, and Greggor A. Zoltners
  • ​book​New Sales. Simplified.: The Essential Handbook for Prospecting and New Business Development — Mike Weinberg
  • ​book​The Prosperous Coach: Increase Income and Impact for You and Your Clients — Steve Chandler and Rich Litvin
• Books on sales strategy
  • ​book​The Sales Acceleration Formula — Mark Roberge — A roadmap for startup sales management
  • ​book​Predictable Revenue — Aaron Ross and Marylou Tyler — A practical summary of best practices for personal selling and sales management based on Aaron’s experience at Salesforce.com.
    • An Argument for Specialized Sales Teams—An Interview with Aaron Ross — Aaron Ross and David Skok
  • ​book​The SaaS Sales Method for Sales Development Representatives: How to Prospect for Customers — Jacob vanderKooij and Fernando Pizarro
  • ​book​The SaaS Sales Method for Customer Success & Account Managers: How to Grow Customers — Dominique Levin and Jacob vanderKooij
  • ​book​Blueprints for a SaaS Sales Organization — Jacob vanderKooij and Fernando Pizarro
  • ​book​The SaaS Sales Method for Account Executives: How to Win Customers — Jacob vanderKooij
• Books on sales methodologies
  • ​book​The Challenger Sale: Taking Control of the Customer Conversation — Matthew Dixon and Brent Adamson
  • ​book​The Challenger Customer: Selling to the Hidden Influencer Who Can Multiply Your Results — Matthew Dixon, Brent Adamson, Pat Spenner, and Nick Toman
  • ​book​SPIN Selling — Neil Rackham
• Books on sales for everybody
  • ​book​How to Win Friends & Influence People — Dale Carnegie
  • ​book​To Sell Is Human: The Surprising Truth About Moving Others — Daniel H. Pink
  • ​book​The Art of the Sale: Learning from the Masters About the Business of Life — Philip Delves Broughton
  • ​book​Influence: Science and Practice — Robert B. Cialdini
  • ​book​Predictably Irrational: The Hidden Forces That Shape Our Decisions — Dan Ariely
  • ​book​Start with Why: How Great Leaders Inspire Everyone to Take Action — Simon Sinek
  • ​book​Confessions of an Advertising Man — David Ogilvy and Sir Alan Parker
  • ​book​Way of the Wolf: Straight Line Selling: Master the Art of Persuasion, Influence, and Success — Jordan Belfort

Communities

• Bravado
• LinkedIn: Sales Best Practices
• LinkedIn: Sales & Marketing Best Practices
• Sales Hacker
• r/sales

Newsletters and Blogs

• For Entrepreneurs—Sales & Marketing
• Chaotic Flow
• The Bridge Group
• SaaStr Academy
• Close.io Blog

Podcasts

• ​audio​23 Sales Podcasts Every Rep Should Listen To — Aja Frost
• ​audio​54 Bad Ass Sales Podcasts Every Sales Professional Should Follow in 2019 — Max Altschuler

Case Studies

• Inside Sales Best Practices: HubSpot—A Case Study — David Skok and Mark Roberge

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