Guest: David Cancel, founder and former CEO of Drift; founder of Rey
After HubSpot acquired his company Performable in 2011, David Cancel became his acquirer’s Chief Product Officer — and didn’t give any thought to how long he’d be in that role. When he started eyeing the exit a few years later, he was told that wasn’t an option: HubSpot had already filed to go public, and an officer of the company leaving in the first 18 months would raise major red flags. “Maybe this is what’s led me to be an entrepreneur,” David recalls. “I can never feel trapped … Someone telling me, ‘you can’t leave,’ I was like, boom. Switch went off in my head … and I was like, ‘I’m out.’” The filing was ultimately delayed and David was able to quit just before the IPO; one day later, he started his next company, Drift.
In this episode, David and Joubin discuss the accountability of doing something, creating constraints, the Whitney Museum, imposter syndrome, Tony Hawk, John Romero, wandering without a map, conservative spending, Brian Halligan and Dharmesh Shah, Phil Jackson, the voices in your head, Shlomo Kramer, righteous independence, cancel culture and diversity, gut vs. data, and killing ideas with discipline.
In this episode, we cover:
Links:
COO of LinkedIn, Dan Shapero: Discussing Go to Market Leadership
B2B General Manager of Calm, Jim Herbold: Describing ‘Unicorn Meat’
VP and GM at Shopify, Loren Padelford: Breaking the Rules in Sales
SVP Sales Modern Health, Hannah Willson: Overcoming the Stigma of Mental Health in Sales
Chief Sales Officer at Brex, Sam Blond: Recruiting Talent
CRO Cockroach Labs, Jeff Miller: Building an Effective Open Source Go to Market Strategy
VP Sales at Mixpanel, Meka Asonye: Exploring Analytics, High Velocity Sales, and Stigmas
CRO CircleCI, Jane Kim: Leading with Vulnerability and Making Mistakes
CRO TripActions, Carlos Delatorre: The Science of Sales
CRO Obsidian Security, Bob Kruse: Building a Winning Sales Culture
VP of Sales at Palo Alto Networks, Jeff StClair : Discovering, Recruiting, and Coaching Sales Talent
Chief Sales and Success Officer at Slack, Bob Frati: Exploring Slack’s Key Growth Levers and Competition
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