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Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193

Chad Peets is one of the greatest sales leaders and recruiters of the last 25 years. From 2018 to 2023, Chad was a Managing Director at Sutter Hill Ventures. Chad has worked with the world’s best CEOs and CROs to build world-class go-to-market organizations. Chad is currently a member of the Board of Directors for Lacework and Luminary Cloud and on the boards of Clumio and Sigma Computing. He previously served as a board member for Astronomer, Transposit, and others. He was an early-stage investor at Snowflake, Sigma, Observe, Lacework, and Clumio. ----------------------------------------------- Timestamps: (00:00) Intro (01:15) The Way into Sales (07:09) Focusing on a Horizontal Customer Base (13:38) What Sales Leaders Bring Pre-Product that Founders Can't (15:51) What the Right Type of Sales Org Means (22:02) Fixing a Broken Culture Between Product & Sales (24:21) How Big Should ACV Be to Justify a Sales Motion (27:01) Are Founders Hiring Sales Enablement Early Enough? (29:57) Common Mistakes in the Sales & CS Relationship (31:32) Key Lessons from Building Snowflake's Sales Team (34:46) Hire Fast & Fire Fast? (39:30) Why Do Top Reps Turn into Non-Performers (45:26) What Makes a Great Sales Rep (53:17) Mistakes Founders Make in Timing Enterprise Expansion (01:02:23) Quick-Fire Round ----------------------------------------------- In Today’s Discussion with Chad Peet’s We Discuss: 1. You Need a CRO Pre-Product: Why does Chad believe that SaaS companies need a CRO pre-product? Should the founder not be the right person to create the sales playbook? What should the founder look for in their first CRO hire? Does any great CRO really want to go back to an early startup and do it again? 2. What Everyone Gets Wrong in Building Sales Teams: Why are most sales reps not performing? How long does it take for sales teams to ramp? How does this change with PLG and enterprise? What are the benchmarks of good vs great for average sales reps? How do founders and VCs most often hurt their sales teams and performance? 3. How to Build a Hiring Machine: What are the single biggest mistakes people make when hiring sales reps and teams? Are sales people money motivated? How to create comp plans that incentivise and align? Why does Chad believe that any sales rep that does not want to be in the office, is not putting their career and development first? Why is it harder than ever to recruit great sales leaders today? 4. Lessons from Scaling Sales at Snowflake: What are the single biggest lessons of what worked from scaling Snowflake’s sales team? What did not work? What would he do differently with the team again? What did Snowflake teach Chad about success and culture and how they interplay together? ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Riverpoint Capital on Twitter: https://twitter.com/riverpointcap Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #chadpeets #riverpointcapital #sales #venturecapital #salesperson #hiring #product #snowflake #saas

Chad PeetsguestHarry Stebbingshost
Aug 22, 20241h 7mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Chad Peets Explains Why Modern Sales Orgs Fail And Reps Stagnate

  1. Chad Peets, longtime sales recruiter and Sutter Hill investor, argues that most founders don’t understand what great sales leadership looks like and therefore hire the wrong CRO, misbuild their orgs, and misalign product and sales. He explains Sutter Hill’s model of hiring a CRO pre‑product to drive true customer discovery, shape the roadmap, and build the sales playbook from day one. Peets lays out how to design profiles, processes, incentives, enablement, and CS so reps actually perform and businesses scale efficiently instead of bloating headcount and missing forecasts. He’s adamant that today’s biggest problem is reps who won’t sacrifice to develop, especially in remote/inside roles, and insists that intensity, development obsession, and in‑office learning still separate top performers from everyone else.

IDEAS WORTH REMEMBERING

5 ideas

Founders usually hire the wrong CRO because they don’t know what ‘great’ looks like.

Peets says the most common mistake to $10M ARR is a mis‑hired CRO who then builds the wrong org; founders need advisors/boards who truly understand elite sales leadership and can define the right profile before hiring.

Hire a CRO pre‑product to own discovery and shape the roadmap.

Sutter Hill brings in a CRO before GA so thousands of prospect conversations inform what gets built, which ICP to prioritize, and which features actually expand sellable TAM, instead of hoping engineering guesses right.

Great sales orgs hard‑wire collaboration between product and sales around ICP expansion.

The CRO should co‑own the roadmap with product, tying specific features to ICP expansion and headcount plans; if product misses commitments, reps are blocked, forecasts miss, and friction and churn escalate.

Process and profile discipline beat ‘committee’ hiring and ad‑hoc interviews.

Peets insists on tight, binary interview steps run only by people expert at selling or qualifying, a clear rep profile, and refusing “my buddy” hires or extra opinionated interviewers (e.g., engineers) that slow and distort decisions.

Incentives must be engineered to drive the exact behaviors the business needs.

Whether it’s paying more on expansion than land, tying reps to the full customer journey, or avoiding over‑booking in consumption models, compensation design is how you prevent misbehavior and unlock the right motion.

WORDS WORTH SAVING

5 quotes

You need a salesperson to create the sales playbook. What does a VP of engineering know about creating a sales playbook?

Chad Peets

If you have a low gross retention number, you’ve got problems.

Chad Peets

If a sales inside salesperson is not willing to make the sacrifice of a 30‑minute commute every day to further his own career, I don’t want that person.

Chad Peets

If you’re gonna make a decision after three weeks, there needs to be an HR issue. Otherwise, your job is to make that rep successful.

Chad Peets

In order to make the right hire, you first have to know what you’re looking for, and most of them don’t even know what they’re looking for.

Chad Peets

Chad Peets’ path from stockbroking to top software sales recruiter and investorHiring CROs pre‑product and using sales to drive true product‑market fitDesigning the “right” sales org: roles, profiles, process, and alignment with productComp, incentives, productivity, and the economics of inside vs. field salesCustomer success, expansion, churn, and the land‑and‑expand motionRecruiting, interviewing, onboarding, and fixing (or firing) sales mis‑hiresCultural shifts in sales: work ethic, remote vs. office, and generational expectations

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