CTO Wisdom with Freedom Dumlao | Beyond The Program

The Pair Program

CTO Wisdom with Freedom Dumlao | Beyond The Program

Welcome to CTO Wisdom. In this series, we interview technical leaders who have stepped into executive positions.Today’s guest host, Eric Brooke, speaks with Freedom Dumlao, CTO at Vestmark, in this episode of CTO Wisdom. We sit down with Freedom to explore his unconventional journey into tech and the leadership lessons he’s learned along the way. From programming on a black-and-white TV as a kid to leading engineering teams at Zipcar and Wayfair, Freedom shares valuable insights on building high-performing teams and navigating executive responsibilities.

Together, they dive into topics such as:

• How a passion for making sparked a tech career
• Lessons from managing managers and scaling teams
• Navigating the CTO role with empathy and accountability
• The future of AI in engineering organizations
• Why shipping culture beats everything

About today’s guest: Freedom Dumlao is the CTO at Vestmark, with a background in leading engineering teams at companies like Flexcar, Zipcar, Wayfair, Drift, and Amazon. He brings deep experience in scaling technology organizations and driving innovation across both startups and large enterprises.

About today’s host: Eric Brooke has a rich and varied leadership career – leading up to 21,000 people and Billions in revenue, throughout 14 countries. In their career, they have been an Executive six times (e.g. President, CEO, CMO, and CTO) and a Board member of multiple organisations. Eric has been a CTO of scaling startups from 0 to 120 engineers. As an adviser and mentor, they have helped multiple other startups scale both in Canada and the US. As well as supporting multiple startup incubators such as 1871 in Chicago and TechStars.Exploring your next tech role? Get insider job advice and the latest startup & govtech openings – delivered straight to your inbox.

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