Kimberly Figenbaum

CFP, CRPC

CFP, CRPC

Managing Director/Investments

6172357813

Kimberly began her financial services industry career in 1993 as a Financial Representative at Fidelity Investments. She would eventually move into a Relationship Manager role at Fidelity in 1996 before taking an opportunity in 2002 to become a Senior Financial Advisor at Merrill Lynch. In 2009, Kimberly moved to Winslow, Evans & Crocker, where she had a 12-year run as a Vice President/Financial Advisor. In 2021, she landed at a predecessor firm of B. Riley Wealth Management as a Senior Vice President/Financial Advisor before becoming Managing Director/Investments in 2024 and joining Stifel in 2025 from B. Riley’s wealth management business. Kimberly earned a B.S. in International Business from Ithaca College in 1991 and holds Series 7, 63, and 66 securities licenses.

Kimberly leverages her experience and insights to support affluent clients, families, and small businesses. Having earned both the CERTIFIED FINANCIAL PLANNER® certification and Chartered Retirement Planning Counselor™ designation, one of Kimberly’s primary focuses is helping clients plan for retirement. She not only looks at her clients’ savings and investments, but also Social Security benefits, long-term care expenses, cost of living, and Medicare. Kimberly prides herself on spending time getting to know her clients and understanding their goals before developing a holistic plan that prioritizes what matters most to them. She finds satisfaction in helping clients enjoy the retirement they envision for themselves.

Kimberly and her husband are Massachusetts natives, and they enjoy the close ties and fun gatherings they have with family and friends. As a longtime resident of the historic Charlestown neighborhood of Boston, Kimberly enjoys walking her dog and soaking in all that the Boston cultural scene has to offer, such as theatrical performances and new restaurants along with the historical sights, museums, outdoor gardens, and greenways in the Charles River and Boston Harbor areas. She is also an avid traveler who likes to read and meet with her book club, take Pilates and yoga classes, and explore the mountains and lakes of northern New England.

Kyle O'Brien

Associate Vice President/Investments

6172357859

Kyle began his financial services career in 2016 at Boston Partners Financial Group in Andover, Massachusetts. In 2018, Kyle joined Winslow, Evans & Crocker in Boston as an Investment Advisor before landing at a predecessor firm of B. Riley Wealth Management in 2021 as an Investment Advisor Representative. He joined Stifel in 2025 from B. Riley’s wealth management business. Kyle graduated from Bentley University with a B.S. in Finance and was a member of the ice hockey team. He holds Series 7, 63, and 65 securities licenses.

Kyle works with individuals, families, and businesses and develops customized investment and wealth management plans specifically tailored to the financial needs and goals of each client. Originally from Tewksbury, Massachusetts, Kyle now lives in Grafton, Massachusetts, with his wife and son. In his free time, he enjoys playing hockey and golf.