As a CEO and corporate leader across fintech, cybersecurity, and financial services, Garrett has built and led organizations from a dozen to 700 people, refining the leadership practices described in his Substack series, The Flannel CEO. With a background in software and data engineering and business analytics, and as a CFA® Charterholder, Garrett blends analytical rigor with people-first leadership to drive growth, scale, and culture. Most recently, Garrett led the cybersecurity company Critical Insight through strong growth, with repeated recognition by Gartner in the MDR Market Guide, by Inc. 5000 as one of the fastest growing companies, and by Washington’s Best Places to Work, including a top-10 ranking in 2021.

Garrett is now founder and managing principal for The Flannel CEO, which offers business strategy execution consulting and executive coaching services.