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Tobi Silver


Sterling Resources, Ltd.

Hingham, MA, USA

Tobi Silver
Stuart Siegel
Engel & Volkers
Mortimer Singer

Tobi Silver’s Biography

Tobi Silver is President of boutique life insurance agency, Sterling Resources Ltd. Sterling's focus is ultra-high-net worth families, both in the US and globally, and prides itself on its impeccable service and customized approach to each family or individual’s unique requirements. Tobi works in partnership with clients and their advisors to create and implement bespoke life insurance portfolios.

She has been with Sterling Resources since the company was founded in 1989. As the company has grown, she has taken on a wide range of responsibilities and was appointed the firm's Chief Financial Officer, then Chief Operating Officer.

Now in a more client-facing role as President, working with trust and estate advisors, tax planners and wealth managers, she heads all advanced underwriting tasks, utilizing her more than 30 years’ experience specializing in private and corporate split dollar plan evaluation and implementation. Tobi also contributes to the ongoing development of planning tools and portfolio stress testing.

With a background in finance and information systems, Tobi approaches each project as a technician. This is a mindset that helped her lead the development of the company’s service department. Also, despite the insurance industry being fairly new to her in her early days, she is now the firm's leader in translating its values and vision to clients.

In recognition of her expertise, Tobi was invited to give a presentation titled “The Value of Life Insurance for High-Net-Worth Investors” at a 2019 TIGER 21 event in Boston. TIGER 21 is a leading peer membership network of high-net-worth entrepreneurs, investors and executives.

Tobi earned a BA, magna cum laude, in Economics from the University of Massachusetts at Amherst and holds an MBA in Finance and Information Systems from Northeastern University. While at Northeastern, Tobi was also inducted into Phi Beta Kappa.

Tobi Silver’s Background

Sterling Resources, Ltd.
1989 - Present
Hingham, MA, USA
Sterling Resources Ltd has over three decades of experience in the life insurance industry, and specializes in meeting the complex needs of the ultra high net worth family.
Marketing & Information Systems
1988 - 1989
Boston, MA, USA
MassMutual offers life insurance and protection products, retirement and investment services to help individuals and families meet their financial goals.


Putting the “Family” in Family Business: It’s Worth It
Tobi Silver joined Mitzi Perdue to discuss how Sterling Resources has created an ideal family atmosphere amongst its employees. “We think of ourselves as family members working in the family business," Tobi says, while elaborating on how the company has been able to maintain this work environment and how it connects to Sterling's relationship with clients.


Why Life Insurance Portfolios Must Be Audited
May 2018
Tobi Silver, President of Sterling Resources, was asked to contribute her thoughts to this article on 'key person insurance' for companies published by CFO Magazine.

Speaking Engagements

Sep 2019
Boston, MA, USA
Tobi Silver was invited to present her study titled “The Value of Life Insurance for High-Net-Worth Investors” to the Boston Tiger 21 chapter. Tiger 21 is an exclusive peer membership network of high-net-worth entrepreneurs, investors and executives.

Tobi Silver’s Education

Northeastern University
MBA | Finance & Information Systems | Phi Beta Kappa
University of Massachusetts, Amherst
BA, magna cum laude | Economics