The Chief Strategy Officer Podcast
The Chief Strategy Officer Podcast brings you conversations with global executives who lead strategy to share their unique experiences in tackling complex challenges, navigating disruptive technologies, and driving impactful growth.
The Chief Strategy Officer role can be lonely and misunderstood. In today's interconnected world, no single leader has all the answers. To learn more about how Outthinker's network of leading chief strategy officers can offer you time-saving solutions, trend insights, and invaluable peer connections - visit outthinkernetwork.com.
The Chief Strategy Officer Podcast
#20—From Founder-Led to Function-Led: Scaling Strategy with Michael Drexler
Today’s guest is Michael Drexler, Chief Strategy Officer at Brightstar Capital Partners, a private equity firm that invests in closely held, middle-market businesses and helps them scale into professional, process-driven organizations.
Michael’s career spans leadership roles across investment banking, global strategy, and private equity—from Barclays to the World Economic Forum, and Brightstar Capital Partners—giving him a rare perspective on how strategy functions evolve as companies mature from founder-led to institutional scale.
In this conversation, we unpack lessons from Michael’s career leading strategy functions and explore how the head of strategy role transforms along a company’s growth journey.
Things we will cover:
- How strategy evolves from a “chief of staff” role in founder-led companies to a full-fledged internal consulting function
- The mindset shift from advising a single CEO to influencing a broader leadership team
- How to build and sustain an effective strategy team—including Michael’s “2-to-4-year rotation” and “no bad news for two weeks” rules
- Why private equity firms view internal strategy functions differently—and how to reposition your team in a PE environment
- Michael’s four-step framework for prioritizing projects that’s “never failed him once”
From developing consulting-style skillsets inside corporations to balancing neutrality among competing executives, Michael brings clarity and practicality to what it means to be an effective CSO.
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