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:
CRO Gong, Ryan Longfield: Finding Comfort in the Uncomfortable: Redefining Failure
CEO Cassidy Ventures, Brendon Cassidy: LinkedIn, Echosign + Talkdesk: Building Successful Startup Sales Teams
CRO Box, Mark Wayland: Forging Positive Sales Cultures
VP Sales Impossible Foods, Dana Worth: From Gourmet to Fast-Food: How He Built Impossible Foods’ Go-To-Market
CRO Cloudflare, Chris Merritt: Creating an Authentic Content-driven Strategy
SVP Salesforce, Mike Wolff: Tips for Becoming a More Effective Sales Leader
CSO Relativity, Peter Kim: The Values of a People-Centric Leader
CRO PagerDuty, Dave Justice: The Principles of Successful Crisis Leadership
CRO Amplitude, Matt Heinz: Exploring The Mindset of a Successful Sales Leader
SVP Global Strategic Services at UiPath, Jay Snyder: Driving Customer Engagement Through Value-Based Selling
CRO Clari, Kevin Knieriem: Exploring the Benefits of Data-Driven Sales
CRO ServiceTitan, Ross Biestman: ‘Team Before Self’: Motivating High-Performing Salespeople
CRO Snowflake, Chris Degnan: Building Snowflake’s Successful Sales Organization from the Ground Up
CRO Flexport, Will Urban: Streamlining Global Trade With Revolutionary Technology
Founder and CEO of Applied Intuition, Qasar Younis: Creating Customer-Oriented Company Cultures
Board Director at Fastly, Kelly Wright: How She Went from Selling Door to Door to Board Director
CRO Auth0, Dave Wilner: Discussing Growth and Leadership
CRO Atlassian, Cameron Deatsch: Exploring Atlassian’s Unorthodox Strategy
CRO Twilio, Marc Boroditsky: A Behind the Scenes Look at Twilio’s Go to Market Strategy
SVP and Head of Sales at AppsFlyer, Mar Brandt: Leadership Insights
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