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 the 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 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 has participated in numerous fundraising and M&A transactions and has practical experience with both successful and challenging deals. He recently led Critical Insight through a complex sale process, working closely with the board and negotiating with multiple stakeholder groups across the capital stack to close a transaction that preserved the mission, ensured continuity for customers, and delivered the strongest economic outcome available within a challenging market.

Earlier in his career, Garrett served as CEO-in-Residence at Madrona Venture Labs, where he led early-stage teams in building fintech product concepts, testing them through market engagement for differentiation and viability. Previously, he was Managing Vice President at Capital One, responsible for the ShareBuilder investing business, having led teams through acquisitions by ING DIRECT USA in 2009 and by Capital One in 2012. His prior roles included Divisional CIO at ING DIRECT ShareBuilder. 

Garrett continues to serve on the Board of Directors and Investment Committee for ShareBuilder 401k.