Who we are

Caleb S. Baker, CLU® – Managing Partner
Caleb joined the GB Financial Group in 2006.  His role is focused on designing, structuring, implementing, and managing life insurance solutions for our clients. He built out GBFG’s modeling system and in 2012 secured an exclusive product designed for long term traditional premium finance.  He actively consults on life insurance product design, comparison, and analysis for Life Insurance Companies, banks, family offices, and insurance firms.

In 2010, he co-founded Windward Capital Partners to help GBFG become the first firm to vertically integrate expertise, design, and execution in both life insurance design and commercial financing.  By securing exclusive lending relationships, WCP allows our clients to have access to the very best terms.  In addition, WCP has become the leader in helping banks evaluate, structure, and manage the financing of life premiums.

In 2019, he co-founded Simplisure after a friend asked about term life insurance.  Simplisure allows consumers to learn about term life insurance, price compare across high quality companies, and apply via a proprietary application process, all online.

Caleb earned his Chartered Life Underwriter, CLU®, from the American College of Financial Services.  He graduated with honors from Gettysburg College in Gettysburg, PA and from IAU, Aix-en-Provence, France. In addition to his studies, Caleb worked to develop a chapter of the charity organization, “Circles of Support” in Gettysburg, which assists low-income single mothers in finding jobs and provides weekly community dinners with childcare.  He continues to be committed to the cause.

Caleb and his wife, Suzanne, and their two sons live outside of Boston. He is fluent in French and is an active member of both The French Cultural Center of Boston and the Boston Sommelier Society.  In his free time Caleb enjoys cooking, running, and free heel skiing.

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