New episode on the Crew Podcast - Brendon Cassidy, former founding sales hire @ LinkedIn (🤯) and GTM legend, helping with the early build out of Gong, Talkdesk, and some other SaaS darlings.
Also, shoutout to our sponsors for this episode, Metaview & 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.
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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.
Brendon’s Background
Brendon Cassidy is the founder of Cassidy Ventures, where he operates, advises, and invests in startups, helping founders with everything from demand and pipeline to their first VP of Sales hire.
He was one of LinkedIn’s earliest employees, then ran sales at EchoSign alongside Jason Lemkin through its acquisition by Adobe, and later at Talkdesk. He was involved with Gong from its inception and has worked with 100 to 150 companies across SaaS and AI, including Higgsfield AI.
He started his career in recruiting and built a legendary career in SaaS sales. Today he spends his time as a sounding board for founders and CEOs making the hires that shape their go-to-market.
Discussed In This Episode
Why demand is still the oxygen for growth, and why more AEs just dilute a finite pipeline
Why you can’t hire sales to fix a product market fit problem
The real cost of spinning up outbound, and why founders underestimate it
Advisory boards, relationship capital, and the levels of lift in a warm intro
Game tape over resumes: why a live pitch is the strongest signal in a sales interview
Why candidates should pitch the product they sell every day, not yours
“Salespeople are pathological liars” and the resume that leaves out the bad
The four things to diligence before taking a VP of Sales role
Why 95 out of 100 AI startups won’t make it, and what the dot-com bust taught him
The secondaries problem: Brex, and why companies are staying private
Where AI is actually landing in GTM, from CPQ to AI BDRs moving upmarket
Radical meritocracy and why he promotes from within
Key Timestamps
(06:42) Why hiring more AEs won’t fix demand
(16:34) Why resumes don’t tell the whole story
(22:46) Salespeople are pathological liars
(28:20) Why 95 out of 100 startups won’t make it
(30:59) The problem with secondaries and why companies stay private
(40:21) AI can’t fix product market fit
(42:50) The game film idea for hiring sales
(53:49) Radical meritocracy and promoting from within
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