Geeks Who Lead Podcast
Hear the inside stories of the "geeks who lead at scale" - Directors, VPs and CTOs running software engineering orgs at larger companies with 100+ engineers, and interviews with domain experts who can help those leaders to manage their engineering orgs more effectively.
I'm your host - Peter Bell, I've been helping senior engineering leaders to connect with and learn from their peers since 2010!
This podcast is designed for engineering leaders who want to learn the latest good practices from their peers who are way too busy operating to write an article or publish a book!
Running a software engineering org at scale is hard! You need to manage stakeholder expectations, attract and retain top talent, align and structure your org effectively and keep up with the latest processes and tooling. And that's before we even try to make sense of the potential impact of LLMs and GenAI on managing technical teams.
Our podcast and weekly newsletter provide you with access to hard-won wisdom from top engineering leaders and relevant domain experts. Learn more at https://geekswholead.com/
Geeks Who Lead Podcast
Cultivating Cross-Functional Teams with Cai GoGwilt
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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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