Strategic Clarity in Complex Estate Planning

Pamela Pirone-Benson, Vice President, Estate Planning Specialist, Fidelity Investments

Pamela Pirone-Benson is Vice President, Estate Planning Specialist at Fidelity Investments and a seasoned estate planning expert with a background in law and financial licensure. She specializes in guiding individuals and advisors through complex wealth transfer strategies, combining technical precision with a deep understanding of legacy, family dynamics and long-term financial goals.

Estate planning doesn’t just involve legal documents or tax strategy. It’s about structure, foresight and often, deeply personal decisions. Few professionals navigate this terrain with the technical skill and clarity that Pirone-Benson brings to the table.

A Legal Foundation Built for Real-World Planning

As vice president of Advanced Planning at Fidelity Investments, Pirone-Benson is a key resource for clients and financial advisors seeking to make thoughtful, informed decisions about how wealth is transferred, preserved and purposefully used. With a background in law and over a decade of direct experience in trusts, estates and tax matters, she plays a critical role in helping people align financial strategy with family intent.

Pirone-Benson’s path into financial planning began with the law. After earning her Juris Doctor from Widener University School of Law and a Bachelor of Arts from the University of Delaware, she started her legal career with a clerkship at the Superior Court of New Jersey under the Honorable Sebastian Lombardi. This foundational experience provided early insight into how legal conflicts emerge, particularly those involving families, estates and unclear planning.

Her transition into trusts and estates law was a natural one. She practiced with Goldstein and Bachman and later joined the respected firm Martin M. Shenkman, P.C., where she focused on helping clients design and implement estate plans tailored to their unique circumstances. Her work involved everything from drafting trusts and wills to structuring charitable gifts and minimizing estate tax exposure. Through these roles, Pirone-Benson became adept at understanding legal frameworks and translating them into practical solutions.

Bridging Legal Insight with Financial Strategy

In 2013, Pirone-Benson joined Fidelity Investments, where she works with financial advisors and clients on strategies involving wealth transfer, estate planning, gifting and charitable giving. More than offering technical answers, she helps to build understanding, clarity and long-term confidence.

Her role is both strategic and educational. She designs learning materials, speaks to both advisors and clients and contributes to Fidelity's broader wealth planning content. Topics like inheritance, trusts, legacy wishes and tax efficiency can be dense and daunting; Pirone-Benson's skill lies in breaking them down into what matters most and delivering that information with calm expertise.

Her contributions are visible in Fidelity’s investor education efforts, particularly those geared toward family wealth planning. She emphasizes the importance of planning early, documenting clearly and fostering communication among family members to ensure that legacy intentions are understood and respected.

Pirone-Benson’s qualifications extend beyond law. She holds both the Series 7 and Series 66 licenses, allowing her to operate as a registered investment professional. This combination of legal training and financial licensure gives her a dual perspective that’s rare and highly valuable in her field.

She’s also registered to serve clients in multiple states, including New Jersey, New York, Florida, Connecticut and Texas. Based in the New York City metropolitan area and affiliated with Fidelity Personal and Workplace Advisors in Boston, she works across regional lines to support planning initiatives wherever they’re needed.

Professionals like Pirone-Benson are increasingly essential in today's estate planning environment. Tax laws change, family structures shift, and the tools available to individuals grow more complex by the year. Amid that complexity, Pirone-Benson serves as a clear voice, grounded in law, informed by financial regulation and focused on the people behind the plans.

What sets her apart isn’t just knowledge. It’s her ability to bridge technical concepts with human concerns, translating legal and financial complexity into guidance that feels clear, relevant and personal. She ensures that trusts aren’t just legal documents, but reflections of long-term goals; that gifts are structured to support, not burden; and that legacies are planned with both heart and foresight.

Pirone-Benson’s work combines depth, discipline and a steady commitment to getting the details right. Whether speaking to financial advisors or working one-on-one with clients, she brings perspective, professionalism and a clear sense of purpose. Estate planning may not always be simple, but with professionals like Pirone-Benson guiding the process, it becomes far more manageable and, ultimately, more meaningful.