New episode on the Crew Podcast - Mark Roberge, co-founder @ Stage2 Capital + former CRO @ Hubspot (was their founding sales hire though the IPO + past 100M in ARR).
Mark’s a legend and a dream guest I’ve wanted to have on for a while. I spent a weekend earlier this year reading his new book Science of Scaling and it was music to my ears, did my write up on it here.
As you all know, I believe sales to be more of a science than it is an art. Some more thought on that here.
Buy his book, it was incredible - 100% of the proceeds from the new book going to mental health causes.
Also, shoutout to our sponsors for this episode, Attention & Metaview. Been awesome working with both of these teams for recruiting, and now infusing as part of our media arm.
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Some of our previous guests:
Eleanor Dorfman, Head of Commercial Sales @ Anthropic, see here
Pat Forquer, CRO @ Legora, see here
Tomer Chernia, VP of GTM @ Cursor, see here
Graham Moreno, VP of GTM @ Parallel
Liam Mulcahy, Head of Sales @ Parallel (former GTM Operating Partner @ Kleiner Perkins)
Becca Lindquist, Head of Sales @ Clay
Nick Bogaty, CRO @ Vercel
Kyle Parrish, former VP of Sales @ Figma
Ghazi Masood, CRO @ Replit
Evan Cassidy, VP of Sales @ Decagon
James White, VP of Sales @ Rogo
Mark Ebert, SVP of Revenue @ Profound
Rob Saliterman, VP of Sales @ Harvey
Bardia Shahali, VP of Sales @ Granola
And many more in the pipeline - if you know any good leaders who fit this, shoot me a DM/reply/email ( [email protected] ). We’ll keep openings rolling and be super open to suggestions for similar guests.
We film in-person in SF & NYC at legit podcast studios and have retained a stellar post-production agency, so the quality will be high.
behind the scenes filming our episode with Graham Moreno, VP of GTM @ Parallel, back in May 2026
Links To Sections
Mark’s Background
Mark Roberge is co-founder and Managing Director at Stage 2 Capital, a VC firm backed by ~1,000 LPs who are all go-to-market operators - including the founding CRO of Snowflake and revenue leaders at Anthropic, OpenAI, Databricks, and GitHub.
Before that, he was the fourth hire at HubSpot and its founding CRO, taking the company from $0 to $100M in revenue through its IPO.
He now teaches entrepreneurial sales at Harvard Business School - a class that had 550 students and 70 sales coaches on staff last year - and is the author of The Sales Acceleration Formula and The Science of Scaling, with 100% of the proceeds from the new book going to mental health causes.
Discussed In This Episode
The pattern behind the IPOs and the bankruptcies: the wrong call on when to scale revenue and how fast
Why board-level scaling decisions get made at what he calls a kindergarten level
The dilution trap: promising 3 million to 30 million to protect your valuation, then having to hire 27 reps to make it true
Blitzscale risk by category, from AI customer support with 20 funded competitors to software for airports
Why almost nobody can define product market fit, and his case for defining it as value creation
P% of customers do E event every T time, and the North Star metric Slack actually had
What is broken in venture capital, and why Stage 2 pairs a career investor with a career operator on every deal
The most common answer to what founders look for in a first sales hire, and why it lands them bottom-half performers
The coin-operated rep: a great growth-stage hire and a terrible pre-PMF one
Why he wants candidates to cheat with AI in the interview
The four phases of AI in go-to-market, ending with buyer agents purchasing from seller agents
Interesting Takeaways
1. The Most Critical Decision In Startups Is Made At A Kindergarten Level
The book came from a 2019 reflection: five years out of HubSpot, ~20 boards, hundreds more companies through his students - one IPO, a couple billion-dollar exits, and a bunch of bankruptcies.
The pattern separating them was the wrong call on when to scale revenue and how fast, and looking back at how those board conversations went, his words: "it was kind of embarrassing how kindergarten level those decisions were made."
His jab at my alma mater: how many MBA classes did you have on how to account for revenue versus how to scale it? The whole thesis is making that decision as formulaic as accounting.
2. The Treadmill Is A Valuation Negotiation In Disguise
Why founders scale too early: they win the valuation fight by convincing the VC they'll go $3M to $30M next year, then wake up owing the number - "I need 27 reps at $1M each, hire them next week."
On the other side, a VC has 20 to 30 bets this decade and only needs 10% to hit, so they want you going as fast as possible to find out quickly if you're one of them.
And if you're not? They'll probably resign from your board.
3. Hire 10 Reps A Month, Not 100 In January
Before you set hiring pace, assess the blitzscale risk of your category. One of his portfolio companies is in AI customer support where 20 competitors have raised $100M+ - they have to go fast, 10 reps a month.
Another sells airport software into five-year contracts and RFPs against incumbents built in the 70s - 2 reps a quarter, not 8 at the start of the year.
Either way, the rule is the same: never lump-sum hire off a fundraise or a fiscal year. Establish a pace and adjust.
4. You Can Sell Ice To Eskimos. That's Not PMF.
Ask a room what product-market fit is and you'll hear revenue, customer count, or inbound leads - all measures of pull, not value.
His definition: consistently creating value for your customer, quantified through retention. Since real retention takes a year to show up, track a leading indicator of retention: P% of customers do E event every T time (Slack's was 80% of customers sending 20 messages every month).
Make that your north star instead of "$1M in ARR" and you still end up with the million - it's just much healthier revenue.
5. Nobody Is Measuring Selling Time
Reps historically spend 12-15 hours a week actually interacting with buyers. AI can push that to 25-30, and with the same rep, same quota, same product, that alone takes a $250K/quarter rep to ~$445K.
ACV, close rates, and sales cycles are all bottlenecked by the buyer - active opportunities per rep is the one lever completely in your control. His homework for every sales leader listening: "set up an agent to measure how often your reps are interacting with customers... benchmark it and double it."
He ran this exact play at HubSpot - refused to scale 4 reps to 20, split the bigger quota across the existing team with pay upside, and they finished 2.5x above the legacy team.
Key Timestamps
(02:06) The pattern behind the IPOs and the bankruptcies
(04:01) Hiring sales too early, and the VC treadmill
(08:38) The dilution trap
(13:26) Value creation, not revenue creation
(21:33) What is broken in venture capital
(33:42) The biggest hiring mistake founders make
(41:36) "I want them to cheat with AI"
(46:51) Selling time: 12 hours a week to 25
Thanks for tuning in!
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For those who are new, my name is Chris Balestras, co-founder & head of talent, media, & brand @ Crew - a GTM recruiting, media, and investing firm, working with seed through series D AI-natives to help them grow.
Where to find Crew:
We work with many of the hottest AI-native startups in various capacities, and for those who are interested, shoot me an email at ( [email protected] ) or a DM on LinkedIn.
🫡 cheers,
Chris