New type of content pillar for the Crew podcast / our media brand: a roundtable episode (over some bourbon), inspired by The Shop by LeBron back in the day.
Was lucky enough to have all four of these guys already on the podcast, check them out + plan to have them on again 1:1 as a “one year in review” or catch-up eventually. But for those who aren’t familiar, we had on:
Liam Mulcahy, GTM Leadership @ Parallel
Jack Gashi, VP Sales @ Avoca
Mark Ebert, SVP Revenue @ Profound
Todd Busler, Head of Sales, Americas @ Clay
We’ll start to test out some of these new formats, let me know what you think!
Also, shoutout to our sponsors for this episode, Parallel & Attention. Been awesome working with both of these teams for recruiting, and now infusing as part of our media arm.
Both incredible products used by a bunch of the AI-natives we work with.
Parallel: Where AI agents find answers - a web index built from the ground up for AI. GTM engineers use it to run real-time account monitors (funding rounds, exec changes, product launches) and automate research and enrichment at scale. Try them here.
Attention: Put a team of revenue agents on every deal. They capture all your customer interactions (without a bot), update your CRM, best engage on your deals, cleanly automate all reporting, score opportunities and reps against any framework, and forecast in a way you can actually trust. The fast-growing companies like Lovable, Avoca, Abridge, and hundreds of others rely on them. Check them out here.
Some of our previous guests:
Eleanor Dorfman, Head of Commercial Sales @ Anthropic
Pat Forquer, CRO @ Legora
Graham Moreno, VP of GTM @ Parallel
Tomer Chernia, VP of GTM @ Cursor
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
Background
Four sales leaders running revenue at AI-native companies sat down with Chris to talk about what the job actually looks like right now.
Territory plans that get thrown out mid-year. Comp models nobody has figured out. And the thing candidates never hear before they sign, which is that the first year is going to hurt.
The conversation runs through deal caps and inbound throttling, why a four-month paper process feels broken to founders who watched the eval close in two days, and how each of them decides whether a candidate wants to learn the game or just extract from it. It closes somewhere more personal, on the conversations these guys had at home before taking the job.
Discussed In This Episode
Why annual territory and capacity planning falls apart when you hire this fast
Which things should stay written in pencil and which need to be written in pen
Deal caps and shutting off inbound to stop reps from sitting on pipeline
Why AE productivity benchmarks are made up right now, and everyone knows it
Jack on why equity is the wrong thing for most AEs to optimize for
Coin-operated vs. money-motivated, and how to tell them apart in an interview
The conversations these leaders had with their spouses before saying yes
Hiring people with young kids as a deliberate advantage
Interesting Takeaways
1. Everything's Written In Pencil. Except The Paper Process.
Nobody at the table spends real time on annual planning anymore, because the plan gets thrown out two months later. Jack admitted this year's goals were set with roughly the logic of "I don't know, make it higher." Liam's counter: you can't take everything down to the studs every month. The product can change weekly, but some things have to be written in pen, like the fact that you can finish an eval in two days and Fortune 50 paper will still take four months. Founders see the eval results and can't understand why the deal isn't closed. Liam's answer: "we've only just begun to fight."
2. "Did You Watch The Video?" Is Dead
With products shipping monthly (sometimes weekly), old-school enablement doesn't survive. The new model is to build an arena of enablement: standing sessions nobody can book over, flying the whole team in for in-person pricing training, SEs whose only job is knowing exactly where the product is, and AI skills or internal agents reps can pull up mid-call. Once all that exists, not knowing becomes a choice, and the leaders stop being sympathetic. Jack now answers dumb Slack questions by tagging Avo, Avoca's internal agent, in front of everyone. The catch: when he first rolled out skills, only 4 of 28 AEs actually used them.
3. Avoca Killed The AM Team Before It Existed
Everyone is staffing up post-sale for year two and three. Profound went the classic route: pulled sales-leaning CSMs into an AM function, gave them quotas and club eligibility, and made it a rule that an AE and AM never share an account. Jack went the opposite way. Avoca was about to hire ~5 AMs, then realized AEs were already driving most of the upsell revenue. So their one AM went back to being a full AE, TAMs now own renewals and flag upsells, and AEs keep their book indefinitely. The team's reaction when it was announced: a standing ovation. And the sharpest line on the topic: "enterprise AM" is mostly a founder invention, because "we used to just call that a Strat rep."
4. Leave 10% On The Table To Protect The Vibe
By traditional capacity math, most of these teams could double headcount tomorrow, and nobody really knows the right number anymore. Jack watches rolling 30/60-day win rate and deal count per AE like a hawk, and if an AE crosses an open-opp cap, their inbound gets shut off. His logic: an AE with 8 open opps is all over a new lead, one with 30 will "get to it." But he intentionally staffs about 10% below max productivity, because if the floor decides the good times are over, losing the culture costs way more than 5% of output. Mark's tell that you've pushed too far: when your best OG reps start quietly letting deals drop.
5. The Real Negotiation Is With Your Spouse, Not The Founder
Liam said the hardest part of leaving Kleiner Perkins for Parallel wasn't equity, the founders, or the team. It was the conversation with his wife. Their deal: put a helmet on for a year, then reassess, and she holds the nuclear keys if it starts blowing up the family. Jack was even blunter: knowing what he knows now, he wouldn't take the job again, but he's glad he did. He now tracks family presence the way he tracks win rates. Two heavy weeks means he skips the next medium-sized deal trip, and if that deal's odds drop from 80% to 60%, that's the price of lasting in the seat.
Key Timestamps
(03:55) The four-month paper process nobody can explain
(11:53) When your best rep is also shipping code
(20:57) Moving the AM function into sales
(29:55) Why the productivity math doesn't add up
(32:33) Setting a deal cap ten minutes after the meeting
(44:55) Forget the equity
(48:50) Coin-operated vs. money-motivated
(56:36) Hiring someone with a young kid at home
Thanks for tuning in!
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, 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