Growing Business through Enhanced Leadership
If your organization is expanding, you're doing great things. With strengthened management skills, you're ready to lead through the next stage.
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If you are ready to...
Lead the biggest team of your career
Connect mission to measurable results
Transform accountability with negotiated commitments
Spark meaningful, collaborative dialogue
Work hard in a way that is fun
Rally your team around shared purpose
Take your people, and yourself, to the next level
...this is for you.
Take the Flannel CEO Leadership Assessment
I'm not dogmatic. These tools aren't novel. They are a straightforward compilation of best practices from numerous sources, tested and honed in real workplaces over two decades.
My goal is to use what's already working for you and help fill in the gaps.
Purpose-Driven Leadership
Mission-Centered Vision
Annual and Departmental Planning
Negotiated, Measurable Commitments
Clear Work Structures Aligned to Goals
Autonomous Performance Cycles
Transparent Accountability
Congruent Compensation
Culture of Continuous Learning
Space for Joy
Clarity at Scale
Vitality and Resilience
The Flannel CEO is a grounded, practical system of leadership, enabling you to support high-performance, purpose-driven teams working collaboratively towards a common vision, in structures that scale with your organization's trajectory.
About Garrett Silver, CFA
About Garrett Silver, CFA
As a CEO and corporate leader across fintech, cybersecurity, and financial services, Garrett has built organizations from a dozen to 700 people, refining the leadership practices described in the series The Flannel CEO.
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 M&A transactions and has practical experience with both successful and challenging deals. He led Critical Insight through a complex sale process, working closely with the board and negotiating with multiple stakeholder groups across the capital stack, including early- and late-stage investors as well as senior and mezzanine lenders. The resulting acquisition by Lumifi Cyber 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 and built 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, acquired by ING DIRECT USA in 2009 and Capital One in 2012. He continues to serve on the Board of Directors and Investment Committee for ShareBuilder 401k.
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.
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