The Twenty Minute VC

Jordan Van Horn: 3 Reasons Salespeople Fail; How to Make a Sales Playbook | 20VC #918

Jordan Van Horn is a Revenue Leader @ Monte Carlo, the world's first data observability company. Prior to this role, Jordan spent an incredible 4 years in sales at Segment including as VP of Sales leading a sales team of 50+ Account Executives and leading the first international expansion for the company into Dublin. Before Segment, Jordan was at Dropbox for 4 years leading enterprise sales for Dropbox Business in California. --------------------------------------- Timestamps: 0:00 Jordan’s Background 1:50 What Jordan Learned Working at a Winery 4:00 What is a “Revenue Leader”? 5:18 What is a Sales Playbook? 6:10 Who should create the Sales Playbook? 8:23 Is it OK to have your product be for everyone? 10:12 How to document what resonates 12:18 Most common excuse for not hitting quota 14:00 How do you advice sales leaders on discounting? 16:10 What do you do when your champion leaves? Multithreading? 18:00 When is the right time to hire first Sales hire? 22:30 How to know whether to hire experienced or junior? 24:16 Biggest mistake founders make with their first sales hire 26:30 How to structure the hiring process for Sales 35:34 What makes the best presentations? 36:37 Jordan’s Biggest Hiring Mistakes 39:08 The Jordan Van Horn User Guide 42:12 How do you nurture and invest in talent? 46:13 The Ideal Onboarding Process for New Sales Hires 49:08 Most Common Red Flags that a New Sales Hire Won’t Work Out 50:25 How do you determine quality of Sales Reps? 53:07 How soon do you let new Sales Reps meet customers? 54:20 How to Structure a Deal Review 56:34 Which sales tactics haven’t changed the past 5 years? 57:41 Which sales tactics have died in the past 5 years? 58:23 What advice would you give to a Sales Leader starting today? 1:00:30 What would you most like to change about Sales? 1:00:58 Hardest Thing about Jordan’s Role at Monto Carlo 1:01:24 First Thing to Break When Scaling 1:02:30 Which company’s sales strategy have you been most impressed by? --------------------------------------- In Today's Episode with Jordan Van Horn We Discuss: 1.) Entry into the World of Sales: How did Jordan make his way into the world of sales first with a vineyard? What are 1-2 of the biggest takeaways for Jordan from seeing the scaling sales teams at both Segment and Dropbox? How did seeing that impact his mindset? What does Jordan know now that he wishes he had known when he entered sales? 2.) The Sales Playbook: How does Jordan define "the sales playbook"? What is it not? What five core things should the sales playbook help you accomplish? Should the founder be responsible for the sales playbook? Can it be created by a Head of Sales? How does Jordan advise founders on three signals that now is the right time to bring in a sales hire? How does Jordan advise founders on whether the first sales hire should be a rep or a leader? 3.) The Secrets to Pricing and Discounting: Why does Jordan not care what price customers pay in the early days? If it is not about ARR, what should teams be optimizing for? When does price discipline become important in a company journey? What are the dangers of not having price discipline? What two tools do sales leaders have to use in order to create urgency in a deal closing process? How should sales leaders think about building multiple champions within a potential customer? At what price point is it worth it? 4.) The Hiring Process: How does Jordan structure the hiring process for all new sales hires? What are the must-ask questions that Jordan asks all new candidates? What does he want to see in those answers? Who else does he bring into the hiring process? At what stage do they get involved? What are they testing for? Does Jordan use case studies with candidates? What makes the best? What makes the worst? 5.) The Onboarding: What is the ideal onboarding process for new sales reps? What should founders do and prep for when onboarding their first sales hires? What materials and recordings should they have ready? What are some early signs that a new hire is not working out? How do we measure their impact? For enterprise sales, it takes a long time to close new deals, how can one determine effectiveness of new reps when the sales cycle is so long? --------------------------------------- #JordanVanHorn #MonteCarlo #HarryStebbings #20VC #salestips #sales #salesleaders #entrepreneur #founder #startuplife #onboarding #jobinterview #dropboxmafia

Harry StebbingshostJordan Van Hornguest

Aug 16, 20221h 3mWatch on YouTube ↗

WHAT IT’S REALLY ABOUT

Why Salespeople Fail And How To Build Winning Sales Playbooks

Jordan Van Horn, revenue leader at Monte Carlo and former Dropbox/Segment executive, breaks down why salespeople fail and how to design effective sales playbooks, hiring processes, and onboarding systems. He argues founders must own the first version of the sales playbook, clearly defining the problem, target customer, and reasons to buy now, while recognizing that playbooks evolve significantly as the company scales.
He outlines the three core reasons sales hires typically fail—cultural misfit, lack of motivation, and misaligned or weak skills—and explains in detail how to design interviews, reference checks, and onboarding to detect and prevent these failure modes. Jordan also emphasizes customer-centric selling, disciplined pricing and discounting, and the importance of multi-threading deals to reduce risk when champions leave.
Finally, he shares his approach to people leadership: transparent expectations (via a personal “user guide”), direct feedback from day one, and a heavy focus on postmortems and learning velocity over early ARR, especially in fast-growing enterprise environments.

IDEAS WORTH REMEMBERING

5 ideas

Founders must own the V0 sales playbook before hiring sales reps.

Before bringing in salespeople, founders should clearly document: (1) the problem they solve and for whom (including who it’s *not* for), (2) patterns in wins/losses and what resonates with customers, and (3) the 2–3 reasons customers buy *now* rather than later. This doesn’t need to be pretty, but it becomes the foundation for all future sales scaling.

Continuously refine playbooks from open-ended V0 to highly prescriptive at scale.

Early playbooks must leave room for learning and unknowns; later, as the problem becomes repeatable and the company needs to rapidly onboard dozens of AEs, playbooks must become granular—scripts, discovery questions, deal stages, and clear steps to customer success.

Hire sales only to solve specific go-to-market problems, not product-market fit.

Jordan stresses you should not hire sales to fix weak product-market fit. Hire when you either (a) believe a pro can generate more revenue per lead than you, (b) need to amplify conversations/learning in a fast-moving market, or (c) are overwhelmed by transactional volume—but you still expect to stay close to customers.

Design the hiring process around three failure modes: culture, motivation, skills.

Most failed sales hires fall into: cultural misalignment (they pull the company in the wrong direction), low motivation (reality of startup work shocks them), or misaligned skills. A structured process—deep backward-looking interviews, clear cultural definitions, and rigorous reference checks—should be explicitly built to screen all three.

Use deep backward-looking questions instead of abstract case studies.

Jordan prefers drilling into specific past achievements (quota performance, key deals, setbacks) with multiple levels of follow-up, especially, “What was hard about it?” This surfaces how much of their success was due to environment vs. true skill and resilience, which is critical in PLG-era resumes where brand names can be misleading.

WORDS WORTH SAVING

5 quotes

Startups live and die by simplicity and clarity of thought.

— Jordan Van Horn

Salespeople fail for three reasons: they don’t fit, they don’t want to do the work, or they just aren’t that good.

— Jordan Van Horn

Early days, I don’t care at all about what price people pay. ARR doesn’t matter at all.

— Jordan Van Horn

Customer success starts in the sales process. Employee success starts in the interview process.

— Jordan Van Horn

Sharing your failures and your mistakes is a sign of strength, not a sign of weakness. I actually don’t trust you if you’re perfect.

— Jordan Van Horn

Jordan Van Horn’s career path from wine industry to tech sales leadershipDefinition and evolution of a sales playbook from founder-led to scaled teamsWhen, who, and how to hire the first salespeople and heads of salesReasons salespeople fail and how to structure a rigorous hiring processOnboarding, early performance signals, and managing enterprise reps with long cyclesPricing, discounting, urgency creation, and multi-threading in enterprise dealsPeople leadership: user guides, motivation, culture, and talent development

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