Cai GoGwilt took a fast-tracked, non-traditional road to becoming a CTO at Ironclad. As a non-traditional CTO, Cai sees his role as helping others on the team get unblocked from any issues in their way. This approach has required a bit of humility on Cai’s part as he’s helped cultivate a culture in which engineers have felt comfortable calling him out when he was wrong.

On today’s episode of CTO Connection, Peter and Cai discuss Ironclad’s process for annual planning as well as building cross-functional teams in a rapidly scaling company.

• [00:20] - How Cai became a CTO
• [01:47] - Leveling up product engineering at Ironclad
• [06:03] - Core elements of the CTO role
• [08:54] - Jack of all trades, master of none
• [12:20] - Creating and sustaining culture
• [14:12] - Annual planning cycle
• [18:17] - Hiring a team that cares about the end-user
• [21:27] - Bringing technology to the law
• [22:58] - Cross-functional empathy
• [30:31] - Selecting engineers to thrive in an empathetic culture
• [34:31] - Finding the right applicants in the Bay area

CTO Connection is where you can learn from the experiences of successful engineering leaders at fast-growth tech startups. Whether you want to learn more about hiring, motivating or managing an engineering team, if you're technical and manage engineers, the CTO Connection podcast is a great resource for learning from your peers!

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This podcast episode was produced by Dante32.

CTO Connection