Sep 19, 2024 · 42m · saastr
How to Hire a Great VP of Sales Today with SaaStr CEO Jason Lemkin
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
SaaStr CEO Jason Lemkin examines why 70 percent of first-time VP of Sales hires fail and delivers actionable frameworks for founders to evaluate, hire, and support hands-on sales leaders who can scale enterprise revenue.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Jason holds 99.4% of the talking time here. How this is scored →
Jason as informed peer 0.0 Guest teaching 0.0 Guest disagreement 0.0 Jason pushing back 0.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 13:28 Audience timing query
In an entirely non-adversarial keynote, the audience member briefly interjects with 'How long?' to prompt Lemkin on when executives can step away from direct deals.
Hardest push from Jason ▶ 3:09 Rebutting founder mode in salesLemkin directly challenges the popular tech narrative around founder mode, arguing it fundamentally fails to scale inside sales organizations.
Biggest teaching moment ▶ 13:30 Clarifying executive involvement in salesLemkin educates the audience on why even mega-cap enterprise CEOs like Benioff never fully abdicate customer-facing deal making.
Jason holds their own ▶ 36:00 Deconstructing board biasLemkin demonstrates his domain mastery by dissecting why venture board members consistently fall for superficial sales candidates who fail in practice.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| The Limits of Founder Mode in Scaling Sales | 0 | 0 | 0 | 0 | Jason Lemkin delivers a solo presentation breaking down why the trending concept of founder mode fails when applied to scaling B2B sales teams. The audience member provides only brief affirmative interjections, with zero adversarial pushback or schooling. | |
| Avoiding the Jaded, Broken, and Done Executives | 0 | 0 | 0 | 0 | Lemkin outlines archetypes of sales executives to avoid, particularly those who are jaded, broken, or unwilling to sell directly. The audience participates purely via reactive prompts, leaving dynamic scores at zero. | |
| Staying in the Trenches and Meeting Customers | 0 | 0 | 0 | 0 | Lemkin shares an anecdote about Marc Benioff meeting customers in person to emphasize that sales leaders must stay in the field. An audience member asks a brief clarifying question ('How long?'), but there is no debate. | |
| Demanding Deep Product Mastery and Domain Fluency | 0 | 0 | 0 | 0 | Lemkin stresses that VP of Sales hires must master product nuance and industry fluency before starting rather than relying entirely on sales engineers. The presentation format continues without interactive dispute. | |
| The Necessity of Total Founder Conviction | 0 | 0 | 0 | 0 | Lemkin advises founders never to compromise on hiring a VP of Sales without total gut conviction and commitment to backfill their gaps. This is an uninterrupted keynote monologue. | |
| Debunking the Myth of the Full-Stack Sales Leader | 0 | 0 | 0 | 0 | Lemkin addresses the unrealistic expectation of full-stack sales executives, advising founders to map specific go-to-market motions before hiring. Audience members offer occasional brief agreements. | |
| The True Cost of a Sales Leadership Mishire | 0 | 0 | 0 | 0 | Lemkin breaks down the cascading financial and operational damage of making a bad sales leadership hire. The monologue format continues without cross-examination or opposition. | |
| Evaluating Stretch Candidates Through Proven Recruiting Track Records | 0 | 0 | 0 | 0 | Lemkin explains how to evaluate high-potential stretch candidates by verifying their past recruiting track record with reference calls. The audience merely observes and reacts affirmatively. | |
| Navigating Board Advice and Finding Ambitious Leaders | 0 | 0 | 0 | 0 | Lemkin concludes by warning founders against generic board advice and encouraging persistence in finding hungry, ambitious sales leaders. The talk concludes without combative interaction. |
Statements from this episode (20)
Lemkin: 70% of First-Time VP of Sales Hires Fail
“70% of first VP of sales don't work out. I think I surveyed 11 people and I think 7.8 of them said it. So I think I coined 70%. I've done surveys on LinkedIn for thousands of people. They've confirmed it.”
Lemkin: Failed Executive Hires Are Always the Founder's Fault
“If you make a critical hire and VP of sales or any role at your startup, VP of anything, it's your fault.”
Lemkin: 90% of Startup VP Candidates Don't Know Basic Company Metrics
“I always ask them like a basic question. I'm like, Do you know how much revenue the company has? Do you know how fast they're growing? Do you know how many sales folks are on the sales team? Nine out of 10 of the executives have no idea.”
Lemkin: 'Founder Mode' Does Not Work For Scaling Inside Sales
“Founder mode does not work for sales. It does not work for inside sales.”
Lemkin: Founders' Biggest Mistake Is Exiting Sales After Hiring A VP
“The number one mistake that CEOs founders make when they hire a VP of sales is they exit sales.”
Lemkin: Sales Lacks Efficiency And Scales With Diseconomies Of Scale
“Sales has no efficiencies whatsoever in it. You need even more people the bigger you get. It has dis-efficiencies of scale.”
Lemkin: Paul Graham Never Ran A Founder-Led Sales Company
“Paul Graham may or may not, he's much smarter than I am, much richer, much better investor, but he never ran a founder-led sales company, ok?”
Lemkin: Never Hire Executives Who Blame Former CEOs For Failures
“Don't hire the jaded. The one literally four minutes in your interview, they're telling you how the CEO or the VC screwed them over... Don't hire them. They're going to think the same thing of you about three weeks in.”
Lemkin: 80% of VP of Sales Candidates Refuse to Sell Directly
“80% of the VPs of sales candidates that founders that I know invest in work with ask me to meet. 80%, bring me this guy, gal, whenever, no gender. They just, they won't do the sales themselves.”
Lemkin: Founders Should Pass on Sales Leaders Who Avoid Customer Meetings
“Salesforce is coming up on thirty billion, and Mark Benioff's still out there hustling and meeting with customers. If you're a VP of sales and gunner or CRO, pass. Don't matter what else you like them.”
Lemkin: Tech Companies Stopped Checking References And Requiring Demos In 2020
“No one does reference checks since March, 20, 20. No one asks sales reps to do demos before they hire them anymore.”
Lemkin: Do Not Let A VP Start Until They Master The Product
“I wouldn't let them start until they know the product folds. I wouldn't let them start. Now, best of all is literally give them the, if you really think they're so great, give them the offer, agree on the comp, agree on the equity and say, you know what? Now t…”
Lemkin: Gusto CEO Barred New Executives From Working For 60 Days
“When Josh would hire a new executive, I think he wouldn't let him work for, 60 days.”
Lemkin: A leader's job is backfilling VPs, not micromanaging them
“Your job as leaders with your VPs is not to tell them what to do. It's to backfill them. This is where the founder mode comes in, not to do their job, but to back, not everyone can be great at everything. So you've got to backfill them.”
Lemkin: Inbound-Only Sales Leaders Will Fail In Outbound Models
“If your model is like, 20%, 50%, 80% outbound, and you want it to go up and you love this head of sales, But they've only done inbound, zero percent chance of success.”
Lemkin: Only Two Of 40 Sales VP Candidates Were Willing To Travel
“I interviewed almost. VPs of sales last year, early last year, only two were actually willing to travel. You can laugh only two out of 40.”
Lemkin: Mishiring a VP of Sales Sets Startups Back a Year
“A mishire in a VP of sales sets you back a year.”
Lemkin: Stretch Sales Leaders Must Have Recruited Quota-Hitting Reps
“Make sure, even in a stretch candidate, that they have hired two to three salespeople that hit quota before. Not 20, not 200, but it's not enough if they inherited a team. It's not enough if they were on a sales team. It's not enough if they were an SDR that g…”
Lemkin: Great sales leaders constantly cultivate reps ready to join them
“Any great sales leader always has a couple of folks ready to go with her the next day. They, and I know you got to be careful with this word this day, but it's true. This word, they groom them. They groom them. The best sales leaders are meeting with tons of f…”