Tobi Silver

Tobi Silver is a Managing Principal at Vanbridge with more than three decades of experience in sophisticated life insurance planning, financial risk analysis, and multigenerational wealth preservation. Her work focuses on the intersection of mortality risk, estate liquidity, taxation, and long-term planning for ultra-high-net-worth families globally. Her expertise includes private placement life insurance, advanced underwriting, private and corporate split-dollar arrangements, and the evaluation of insurance as a component of broader diversification and wealth transfer strategies.

Tobi joined Sterling Resources Ltd. at its founding in 1989, subsequently serving as Chief Financial Officer, Chief Operating Officer, and President. Following Sterling’s acquisition by Vanbridge in 2024, she continued her work collaborating with families and their legal, tax, and investment advisors on complex insurance and wealth transfer strategies. With a background in finance and information systems, Tobi brings an analytical perspective to evaluating insurance within broader family wealth strategies and has contributed to the development of financial modeling tools used to evaluate the long-term economic implications of life insurance.

Tobi has presented “The Value of Life Insurance for High-Net-Worth Investors” at TIGER 21 events and participated in a Family Office discussion on planning for liquidity at the Family Firm Institute’s Global Conference at MIT. She graduated magna cum laude from the University of Massachusetts Amherst with a BA in Economics and earned an MBA in Finance and Information Systems from Northeastern University.