The Twenty Minute VC (20VC): 20Sales - The Best Sales People Are F***** in the Head | The Unspoken Truths All Sales Leaders Need to Know in 2026 | Chad Peets (Jan 9, 2026)

Host: Harry Stebbings

Guest: Chad Peets

Episode Overview

This brutally candid and dynamic episode features returning guest Chad Peets—one of the most renowned, no-holds-barred CROs in tech—discussing the hard (often uncomfortable) truths about what it takes to scale elite, mission-driven sales teams. In conversation with Harry Stebbings and co-hosts, Chad unpacks his philosophy on recruiting "obsessed" talent, his methods for evaluating and firing, the evolving landscape of enterprise sales in the AI era, and why most founders and leaders fundamentally get sales hiring wrong. The conversation digs deep into lessons from Chad's work at XAI, Parloa, and more, covering the real cost of underperformance, the future of SaaS and AI sales, and the importance of building resilient, high-grit cultures.

Key Discussion Points & Insights

1. What Makes a World-Class Salesperson? ("A Little F***** in the Head")

[00:00], [12:06]

• Obsession & Grit Over Resume:
  “I need people, just to be blunt, that are a little fucked in the head like I am … at the moment I become conscious of being awake, I’m thinking about work. I can’t help it. I’m obsessed.” — Chad ([00:00])

• Great salespeople possess an almost irrational obsession for winning and learning; it’s not just about making money, but about being the best, the need to win, and changing the way customers buy.

• Chad seeks individuals who work to excel at their craft, not just those "working to fund a passion elsewhere." He values grit, a history of facing real hardship, and a relentless drive to improve.

2. Building Sales Teams at Scale—XAI and Beyond

[06:36], [08:50], [09:38]

• Operator’s Mentality:
  Chad directly involves himself in comp design, CEO/CRO check-ins, and in-the-weeds problem-solving, preferring a hands-on, private equity approach.

• The mission focus at XAI (and among Elon Musk companies) is distinct: "It’s not about money, it’s about mission, it’s about purpose, it’s about doing shit correctly." ([08:50])

• Hiring messaging:
  "You have an opportunity to work for and partner with the greatest entrepreneur … in what is probably the most important technology space ever."
  The flip side: “If you like to hide, this ain't the place. I promise you, either I’ll find you, or somebody else will, and you are not going to make it.” ([10:25])

3. Recruiting Challenges—Europe's Cultural Divide

[11:14], [26:41]

• European market realities:
  Chad (and co-hosts) lament the difficulty of finding the right obsessive, ownership-driven talent in Europe, in part because of entrenched work-life expectations ("I'm going to take the next three weeks off—that's how we do it in Europe.").
• On remote/hybrid: Chad is staunchly in-office for inside sales (“Inside sales is an in-office deal and there can be no exceptions”), and field sales must be physically where the customers are.
• Firing in Europe: Systemic challenges exist: “Try firing somebody in Europe … they’ll be on the books for a year after you want to get rid of them.” ([32:55])

4. Interviewing & Testing for "Obsession" and Grit

[12:44], [14:04], [16:08]

• Questions Chad asks:
  • “What’s your passion?”
  • “What drives you to wake up in the morning?”
  • “Tell me about the hardest thing you’ve ever been through.”
  • “How many net new logos did you bring in?”
• Beyond Quotas: Deep dives into not just what a candidate achieved, but how they achieved it (e.g., details of their largest deal, pipeline generation abilities).

"Somebody that's passionate about their career will know every single one of these details." — Chad ([16:08])

• Risk on inexperience: Zero tolerance for totally green candidates in field or inside sales—some evidence of success required.

5. Startup vs. Big Company Sales DNA

[17:14], [20:00]

• Founders often hire CROs/Heads of Sales for the company they hope to be tomorrow, not for what the company is today.
  “If I talk to 50 CEOs, 48 of them I’m going to very quickly determine are probably not right for me to work with … the CRO you hired is the wrong one, and … I’ll go fire half your sales reps.” ([20:00])

• Chad values candidates with demonstrated experience closing fresh logos, not inheriting or upselling an existing book.

• Cautions against overvaluing industry/domain experience as a substitute for actual sales talent.

6. Measuring & Improving Sales Team Performance

[28:23], [29:39]

• Performance isn’t just quota:
  Chad looks at new customer meetings, steps in the sales process, conversion ratios, and rep presence in the field.
• Attrition benchmarks:
  “We will model 25% attrition … If you start to get above that, you got a problem. If you’re too low, you have a different kind of problem.”
  “You should be shooting the bottom 10% of your sales organization every year.” ([29:35])
• Over-hiring is a must to account for churn and promotions—accept that not every hiring decision will be right.

7. Cultural Realities of High-Performance Sales Teams

[31:49], [43:00], [44:00]

• Firing fast:
  “Will I fire fast? Fucking A, yes, I will fire fast.” ([32:29])
• No fear of unpopularity:
  “You can be disliked. You need to be respected. If your sales leader is beloved by everybody, you got the wrong guy. I want to work for a guy that's going to call me on my shit, that's going to make me better, and who wants to win as badly as I want to win … you cannot win without conflict.” ([44:00])
• Feedback style:
  Chad believes public feedback is about efficiency and collective learning, but admits he could improve at balancing candor and embarrassment.

8. Sales Compensation, Quotas, and Motivation

[35:09], [36:08], [39:10]

• Compensation Benchmarks:
  “If you’re not at least at three times your OTE, you got too many salespeople.” ([35:09])
• Err on the side of quotas "too low" when data is uncertain; too high and good salespeople leave, replaced by B players.
• Comp plans should be designed to incentivize the right balance of new business and expansion.

9. Balancing Intensity & Personal Life

[42:21], [48:57], [50:35]

• Family trade-offs:
  No illusion—success at the highest level demands sacrifice: “I go from hero to zero in a five mile drive every day.”
  “I couldn't have done what I've done career-wise without my wife being a full-time mom. No chance. None. Zero.”
• On raising children with grit:
  “How do you give them that same level of grit and fight without ever having to face those kind of difficult challenges?” ([51:17])

10. AI’s Impact on the Sales Profession

[24:21], [56:39], [57:11]

• AI will dramatically change sales, but enterprise sales is not going away.
  “Notion that the enterprise salesperson is going away … I just don't subscribe to that theory.”
• Significant structural changes coming:
  • AI will rapidly shrink and possibly eliminate SDR/BDRs within five years ([56:39])
  • Role boundaries between sales, pre-sales engineers, and forward deployed engineers are rapidly shifting
• Human relationships are still indispensable at the high-stakes end of the market

11. The Future of SaaS and Sales

[55:14], [65:15]

• End of SaaS?
  “Are the LLMs going to eat that space, or are there going to be independent companies in the AI space? … I think it’s going to be wildly fascinating in five years, and I don’t think anybody knows.” ([55:14])
• The product now matters more than ever:
  “I think sales execution is just as important, but ultimately, if you have a shitty product, you can’t win.” ([65:15])

Notable Quotes & Memorable Moments

• On what makes a sales leader:
  “If your sales leader is beloved by everybody, you got the wrong guy … you cannot win without conflict.” — Chad ([44:00])
• On hiring/firing:
  “You should be shooting the bottom 10% of your sales organization every year.” ([29:35])
• On work/life tradeoffs:
  “I go from hero to zero in a five mile drive every day.” ([48:57])
• On raising children:
  “The world doesn't give a fuck and nobody is coming to save you.” — Chad ([51:17])

Timestamps for Key Segments

• Opening Manifesto: Salespeople have to be "a little fucked in the head"
  [00:00], [12:06]
• Hiring for grit, not prestige
  [14:04], [16:08], [19:14]
• Why founders get head of sales hiring wrong
  [20:00]
• The challenge of firing in Europe
  [32:55]
• On quota setting and compensation dynamics
  [35:09], [36:08]
• Balancing family and work intensity
  [48:57], [50:35]
• AI's impact on sales roles
  [56:39], [57:11]
• End of SaaS? Reflections on the next five years
  [55:14], [65:15]

Final Reflections

This episode serves as a masterclass in sales leadership for founders, CROs, and anyone who wants a reality check on what it takes to build, scale, and maintain high-performing teams—especially in a world shaped by rapid AI evolution. Chad's unapologetic candor offers invaluable lessons on hiring, motivation, leadership, and the future of technology sales.