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.

Learn more about Outthinker's community of chief strategy officers - https://outthinker.com/
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