Kendall Bolt

Kendall is the CEO of SKY and a passionate advocate for helping families achieve clarity, confidence, and peace of mind in their financial lives. He brings a unique blend of institutional finance experience, military leadership, and a deep personal commitment to service. Before joining SKY, Kendall advised Fortune 500 and privately held companies as an investment banker at Bank of America Securities, where he led mergers & acquisitions, IPOs, and capital raises across the industrial and infrastructure sectors. His career began as a U.S. Navy Surface Warfare Officer, where he served in multiple leadership roles and developed the values that continue to guide his work today.

Kendall holds a B.S. in Economics from the United States Naval Academy, where he was the captain of the baseball team. Clients value his thoughtful, disciplined approach and his ability to simplify complex financial decisions. He’s known for listening closely, putting clients’ goals first, and building lasting relationships rooted in trust.

Kendall lives in Fairfield, Connecticut with his wife Madison, their son Hudson, and daughters Marlowe and Demi. He enjoys coaching youth baseball on the weekends and attending local events with his family.