Bobby Pearl

CFP®, APMA®

Financial Advisor

Bobby brings a distinctive, multi-generational perspective to wealth management, shaped by both personal experience and professional discipline. Having witnessed firsthand the impact of City Square Wealth Management’s guidance on his own family over the past two decades, he developed an early appreciation for the enduring nature of trusted advisor relationships and the value of thoughtful, long-term planning.

A graduate of Bowdoin College, where he earned a degree in Economics and Government & Legal Studies, Bobby holds both the CFP® and APMA® designations. He is committed to delivering proactive, highly personalized advice grounded in rigor, clarity, and a deep understanding of each client’s evolving priorities.

Bobby specializes in advising emerging, high-performing professionals and athletes navigating periods of rapid financial growth and complexity. From NIL opportunities to professional contracts and pivotal career transitions, he provides a structured and disciplined approach designed to simplify decision-making and instill long-term financial confidence. Drawing on his experience in highly competitive environments, Bobby understands the demands placed on his clients and serves as a steady, strategic partner by helping them make the most of critical windows of opportunity while building a durable financial foundation.

A former collegiate hockey and baseball player at Bowdoin, Bobby brings a foundation of leadership and resilience to everything he does. That competitive drive recently carried him across the finish line of the 2026 Boston Marathon as a member of the Dana-Farber team—a training journey that even saw him log a run from the city all the way back to his hometown of Wakefield. When he isn't mentoring the next generation of athletes as a coach for the Cape Cod Whalers, Bobby is likely on the golf course or enjoying the coast in Kennebunk or Cape Cod.