Aug 17, 2022 · 1h 3m · news
Jordan Van Horn: 3 Reasons Salespeople Fail; How to Make a Sales Playbook | 20VC #918 · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20VC, host Harry Stebbings interviews revenue leader Jordan Van Horn to dissect elite enterprise sales strategies, covering everything from building a founder-led playbook to interviewing, hiring, and onboarding top sales talent.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 19.2% of the talking time here. How this is scored →
Harry as informed peer 4.1 Guest teaching 5.5 Guest disagreement 2.3 Harry pushing back 3.1
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 19:31 Reframing Founder Workload Reasons
Jordan directly reframes Harry's point that founders hire sellers to reduce personal workload, bluntly stating that hiring sales staff is a founder problem and good luck walking away from sales.
Hardest push from Harry ▶ 44:54 Challenging Jordan on Management DetachmentHarry brings up direct criticism from Jordan's former manager Zhenya, challenging Jordan on whether caring too much for reps prevents him from being an objective sales leader.
Biggest teaching moment ▶ 25:00 Deconstructing Resume Brand BiasesJordan educates Harry on how impressive resumes from hyper-growth companies like Twilio can mislead founders, explaining how early reps often just ride product-led growth waves without demonstrating actual sales execution.
Harry holds his own ▶ 8:16 Pushback on Horizontal ICP PrecisionHarry draws on his knowledge of horizontal software companies like Notion and Dropbox to challenge Jordan's demand for precise target audience definitions in early playbooks.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Jordan Van Horn's Career Journey | 2 | 3 | 1 | 2 | Harry welcomes Jordan and asks about his transition from the wine industry to tech sales leadership at Dropbox, Segment, and Monte Carlo. Harry asks a crowd-sourced question from Zhenya and playfully questions the ambiguity of the title 'head of revenue'. | |
| Defining and Building the Sales Playbook | 5 | 6 | 2 | 4 | Jordan defines a sales playbook into five key steps and distinguishes V0 founder-led playbooks from later iterations. Harry offers informed pushback using horizontal products like Notion and Dropbox to question how precise customer definition needs to be. | |
| Tactics of Discounting and Multi-Threading | 4 | 6 | 3 | 3 | Jordan shares a hot take that early-stage ARR does not matter compared to learning and customer fit, while cautioning against excessive discounting as companies scale. Harry prompts tactical advice on multi-threading to prevent churn when champions depart. | |
| Strategizing the First Sales Hire | 4 | 6 | 3 | 3 | When Harry brings up founders wanting to hire salespeople to reduce their personal workload, Jordan directly rejects the premise, asserting that hiring does not simplify founder responsibilities. Jordan breaks down how pedigree brand names on resumes can deceive founders. | |
| Structuring the Sales Interview and Evaluation | 5 | 6 | 2 | 3 | Jordan outlines why salespeople fail and detailing his multi-stage interview structure, including using negative pressure in initial calls. Harry shares VC alignment on interview mistakes and asks probing questions about pitch presentations versus historical deep-dives. | |
| Post-Hiring: Personal User Guides and Onboarding | 5 | 6 | 3 | 5 | Harry presses Jordan using direct quotes from his team and former boss Zhenya, challenging Jordan on whether his empathy for AEs impedes objective leadership. Jordan explains his public user guide, setting firm work-life boundaries, and upfront transparency. | |
| Evaluating Long Sales Cycles and Post-Mortems | 4 | 6 | 2 | 3 | Harry asks how to evaluate salesperson quality during long enterprise deal cycles before revenue lands. Jordan explains tracking leading indicators and discrete process milestones rather than relying solely on lagging financial outcomes. | |
| Quick-Fire Insights: Sales Evolution and Leadership | 4 | 5 | 2 | 2 | In a quick-fire wrap-up, Jordan highlights discovery as an unchanging sales fundamental and explains why pure top-down sales are dead. He advises new sales leaders to complement their founder's distinct skill gaps. |
Statements from this episode (16)
Dropbox struggled by lacking clarity between consumer and enterprise sales
“I would say that Dropbox did struggle at times with a core identity of whether it was a consumer company or whether it was an enterprise sales company. And so I think that we spent a lot of cycles and we missed a lot of opportunities because we didn't have tha…”
Monte Carlo reached $1B valuation and 80 GTM employees without HR
“One funny thing about Monte Carlo is we managed to get to like a billion plus valuation. We managed to get to an 80 person go to market team, and we still hadn't hired a recruiter or a head of HR.”
Founders must own the initial sales playbook and define anti-ICPs
“A hundred percent a leader of an organization, a founder is accountable for that V zero of that playbook. And that V zero should really only clearly document three things. They're just the foundational go to market pillars. They are what problem are you trying…”
Monte Carlo operates 100% through enterprise sales without PLG
“The lens that I'm looking through today at Monte Carlo is a very specific enterprise tops down sales motion that's focusing on one specific team. And that's why we don't have you know, a product led growth model. It's like all at 100% sales side growth.”
Exploding discounts create a horrible customer experience
“I will either give you an exploding discount. It's 50% if you sign today and it's like no discount if you sign tomorrow, that's a horrible Customer experience.”
ARR does not matter in the early days of a startup
“Early days, I don't care at all about what price people pay. ARR doesn't matter at all. There's a hot take from a sales leader early days. I think the only thing that matters is that you're learning and that you have good customers who are good fits that are g…”
Low ASP sales motions should be single-threaded and move quickly
“It doesn't make sense to build like this multi-threaded, overly engineered you know, go to market motion when you have a 4000 dollar ASP. And so for those lower end of the markets, be single threaded, that's fine, but just move quickly because time kills all d…”
Founders still spend 25% of time selling after hiring first rep
“You're still gonna spend 25% of your time with customers, right? Or prospects. Like that's not gonna change. That's not gonna change for six or nine months.”
Van Horn starts sales interviews by listing Monte Carlo's operational flaws
“I start every first interview, I don't know if it's a good iron practice or a bad one, but I say like, oh man, we have problems. Like, let me walk you through all of the things that are wrong at Monte Carlo and all the things that we need to fix in the next si…”
Asking 'what was hard about it?' reveals a salesperson's actual skills
“There's like a key question that I think gets to all skill set that has been the most powerful question that I ask. It's what was hard about it? Because that question gets to the root of what that person actually did and why their skills are relevant to your c…”
Van Horn has tried to eliminate pitch presentation interviews for seven years
“I've been trying to kill the pitch presentation interview for like seven years and my sales leaders just won't let me do it.”
Sales hiring committees should be kept under six people
“Getting really clear about what the person that you need in this organization, and then keeping that decision-making group to less than six is the third thing that's just so important.”
Managers should know within 30 days if a new hire fits
“You should know within 30 days about whether someone's going to be a fit or not.”
Pure top-down enterprise sales to CIOs using slide decks is dead
“Pure tops down sale. I will never be able to go into a CIO's office and show them a really spiffy deck and give them a customer reference and get a deal, right?”
Monte Carlo reached eight figures in revenue within 18 months
“Growing from like no revenue to like eight figures in revenue in 18 months is really freaking hard. Growing a team from zero to 80 is really hard.”
MongoDB successfully pivoted from top-down to product-led sales
“MongoDB has always impressed me, but it, to go from tops down enterprise led to product led sales you know, in the last couple of years, that's a really hard transition. I don't think I've ever seen anybody do it and they've done it really well.”
Shorts cut from this episode
▶ Salespeople FAIL for THREE REASONS #shorts · 20VC with Harry (@26:46)
▶ How to nurture talent #shorts · 20VC with Harry Stebbings (@43:08)
▶ How to onboard for sales #shorts · 20VC with Harry Stebbings (@46:36)
▶ Hiring people does not make your life easier #shorts · 20VC (@20:12)
▶ Best way to start a job interview · 20VC with Harry Stebbing (@28:11)
▶ The truth about Sales Managers #shorts · 20VC with Harry Ste (@23:40)