Why Most AI Startups Aren't Defensible & Why Sales Teams Fail w/ Brendon Cassidy, Founding GTM @ LinkedIn
The Crew PodcastShow Notes
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 got out after a mentor told him that if you stay in recruiting long enough, you're a recruiter. Today he spends his time as a sounding board for founders and CEOs making the hires that shape their go-to-market.
Timestamps • (00:00) Intro • (01:00) Welcome to the Crew podcast • (02:22) From LinkedIn to EchoSign to Gong • (06:42) Why hiring more AEs won't fix demand • (08:34) How the best companies create demand • (10:22) Advisory boards and warm intros • (16:34) Why resumes don't tell the whole story • (20:16) When to run a live role play • (22:46) Salespeople are pathological liars • (25:56) How to pick the right company to join • (28:20) Why 95 out of 100 startups won't make it • (30:59) The problem with secondaries: Ramp vs. Brex • (37:31) CPQ and contracts in a usage-based world • (40:21) AI can't fix product market fit • (42:50) The game film idea for hiring sales • (49:41) The sales mafias he respects • (53:49) Radical meritocracy and promoting from within • (01:00:00) The bootstrapped company that surprised him
About The Crew Podcast The Crew podcast interviews GTM leaders and investors at top AI startups and early-stage companies. Every week, host Chris Balestras, partner @ Crew, talks to the people actually building go-to-market motions in real time, not in retrospect.
About Crew Crew is a recruiting, investing, & media firm for seed through series D AI-natives & fast-growing SaaS startups. This Episode Is Brought To You By Attention: Put a team of revenue agents on every deal. Attention captures every customer interaction without a bot in the room, updates your CRM, automates your reporting, scores reps and opportunities against any framework, and forecasts in a way you can actually trust. Trusted by Lovable, Abridge, Avoca, and hundreds of other fast-growing companies. Try it at https://www.attention.com/
Metaview: The agentic recruiting platform, built for hiring end to end. Metaview's agents source and reach out to candidates in your own tone, review every inbound application against your criteria and tell you exactly why someone made the shortlist, join every call and deliver structured notes the moment it ends, and surface trends across your pipeline from salary expectations to AI fluency. Recruiters, hiring managers and agents all work off one layer of context, with permissions and a full audit trail behind every output. Trusted by Deel, Brex, Deliveroo, Replit and thousands of other teams. Start for free at https://www.metaview.ai/
Where to Find Crew LinkedIn: https://www.linkedin.com/company/crewgtm YouTube: https://www.youtube.com/@thecrewgtm Website: https://www.withcrew.ai/ Blog: https://www.withcrew.blog/
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