New episode on the Vibescaling Podcast, Tomer Chernia! Definitely one of our more requested guests we’ve had so far, with Cursor being probably the fastest growing AI-native out there.
Been awesome doing these and have so many in the hopper (see below) - thank you all for the kind words and support so far.
Some of our previous guests:
Todd Busler, CEO @ Champify - see writeup here
Raphael Parker, CRO @ Mandolin (former founding GTM hire @ Segment) - see writeup here
Kyle Parrish, former VP of Sales @ Figma, see article here
Liam Mulcahy, GTM operating partner @ Kleiner Perkins, see article here
Pat Forquer, CRO @ Legora, see article here
Mike Donohue, CRO @ Maven, see article here
Some of our future guests for Season One:
Jack Gashi, VP of Sales @ Avoca (recorded, in edits now)
Eleanor Dorfman, Head of Sales @ Anthropic (recorded, in edits now)
Ghazi Masood, CRO @ Replit (recorded, in edits now)
Kyle Norton, CRO @ Owner.com
Jason Gelman, Operating Partner @ Primary Ventures
Evan Cassidy, VP of Sales @ Decagon
Liam Mulcahy is coming on again!
Mike Heller, Partner @ Floodgate (former Dropbox & Clearbit GTM)
Rob Saliterman, VP of Sales @ Harvey
Jaquelyn Goldberg, VP of Sales @ Unframe
Jason Miller, VP of Sales @ Unify
& others from our portfolio companies @ vibescaling
And many more in the pipeline - if you know any good leaders who fit this, shoot me a DM on LI or reply to this email. 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 hired a new post-production agency, so the quality will be high - see below for a snippet in-studio behind the scenes.
Interviewing the awesome Ghazi Masood, CRO @ Replit, in our NYC studio this week
Also, huge shoutout to our sponsor for this one, Centralize (they’re also a portco of ours at Vibescaling).
One of the best tools I've seen for big enterprise deals is Centralize.
The real problem in high-ACV sales isn't effort - it's visibility. Who matters? Who have you talked to? Where are the gaps?
Centralize is your AI deal cockpit. It builds living org charts from your CRM, emails, and calls - showing you who's engaged, what they care about, and who you're missing. No more guessing at multithreading.
Top teams use it (Cognition, Intercom, Brex, etc.) to run cleaner pipeline reviews and close faster.
Check it out at usecentralize.com.
And now, onto the episode 🎙️
Links To Sections
VibeScaling Episode 7: Tomer Chernia
Was definitely excited to finally have Tomer on.
We have a good overlap of connections - he’s homies with Navid (CRO @ Zapier, who hired me @ Metronome) as well as part of the Branch mafia, whom I came to cherish from my time at Metronome (Grady Sokaras, Julian Sheinbaum, Felipe Noguerol, etc).
Tomer is one of the more technical and cerebral GTM leaders I’ve had the chance to interview - his insights on how to cut through the BS in sales interviews is second-to-none, and his ability to consistently surround himself with the best talent networks is something we should all strive for (as he says below, almost the bingo card on the GTM mafias list 😆).
Tomer’s Background
Tomer Chernia is the VP of GTM at Cursor, one of the fastest-growing companies in tech - reportedly going from 0 to $500M+ ARR faster than almost any company in history.
Before Cursor, Tomer spent three years at Vercel where he helped build out the go-to-market motion and hired a team of 100+. Prior to that, he was at Branch and Segment as early GTM hires.
Tomer got his start in tech at Yahoo, then joined Wildfire pre-acquisition by Google - where he caught the startup bug. He even tried his hand at founding a company before going back to sales.
He's a serious foodie (ask him for SF restaurant recs) and recently got into natural wine - a good tip for if you want to get his attention prospecting 🙂.
Interesting Takeaways
"Don't mistake a clear path for a short distance." Tomer learned this the hard way when he left Google to co-found a company with his friend from Wildfire. The startup didn't work out, but two years of building product gave him the technical depth that made him lethal as a seller to developers.
The "three hows" interview technique. Most sales candidates can memorize talking points. Tomer pressure-tests depth by asking "but how?" or "why?" repeatedly until their understanding breaks. The best candidates can go three levels deep on product and connect the dots dynamically.
Skip the pitch, run a discovery session. Tomer stopped asking candidates to pitch his product. Now they do a 30-minute discovery call, take a break, then do a deal review. It's the single highest source of signal in their interview process because you see how people actually wield information when there's no script.
"Buyers are liars" - Tomer doesn't love the phrase, but there's wisdom buried in it. Your champion isn't always the most reliable narrator. You have to develop a holistic understanding of what's happening in a deal, not just trust one person's version of events.
The sandwich approach to selling developers. Bottoms-up, top-down. You need executive access at certain stages, but you can't skip developer buy-in. An open-face sandwich (top-down only) doesn't work. If devs aren't using the product, you're not getting the value.
Sales morale isn't a line item, but it should be. Setting unrealistic quotas doesn't push teams harder. It deflates them. Reps do their best work when they're already at number and in accelerators, coming from a place of confidence instead of desperation.
High-agency teams generate their own pipeline. Even when inbound is overflowing, Tomer wants his reps running outbound. The goal isn't to sit around waiting for the phone to ring. Resilient teams don't rely on marketing to feed them forever.
Why Cursor over OpenAI and Anthropic? Those companies are wildly successful, but they're big. Cursor has the revenue maturity of a company ready to go public but the headcount of a Series B. If you want to leave fingerprints on how a company operates, there's no better place right now.
Discussed In This Episode
His interview process evolution: from "pitch your product" to discovery sessions + deal reviews
The "three hows" technique for testing candidate depth until their understanding breaks
How Cursor went from 8 GTM people to nearly 100 in six months
Why he chose Cursor over staying at Vercel (the "would you regret it?" test)
The Cursor vs. OpenAI/Anthropic pitch for candidates and why "born adult" matters
Why Cursor pays commissions when others don't and the real tradeoffs
PLG sellers vs. top-down sellers and different strengths, different failure modes
Why sales morale matters more than most leaders admit and how quota setting destroys it
"Buyers are liars" and why your champion isn't always a reliable narrator
The future of outbound: signal-based, not spray-and-pray
Timestamps
(00:00) Intro & SF Restaurant Recommendations from a Serious Foodie
(04:00) From Humanities Major to Yahoo: How Tomer Fell Into Sales by Accident
(12:00) Wildfire, Google, Founding a Company & Why He Went Back to Sales
(20:00) The Tap on the Shoulder from Cursor: "Would You Regret Saying No?"
(26:00) How to Actually Hire Great Salespeople: Discovery Sessions + Deal Reviews
(32:00) The "Three Hows" - Testing Candidate Depth Until Understanding Breaks
(38:00) Why Sales Morale Matters: Quota Setting & Rep Motivation
(44:00) Cursor's GTM Growth: From 8 People to Nearly 100 in Six Months
(50:00) Why Cursor Over OpenAI or Anthropic: The "Born Adult" Company
(56:00) The Future of Outbound & How to Stand Out as a Candidate
Thanks for reading!
If you enjoy it, please give us a rating, review, or follow on Spotify/YouTube/Apple Podcasts - it really helps us grow this.
For those who are new, my name is Chris Balestras, partner @ Vibescaling - a GTM advisory, recruiting, media, and investing firm, working with seed through series C AI-natives to help them grow.
Where to find Vibescaling:
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 LI.
🫡 cheers,
Chris