Head of Advice + Planning

As an English major with his sights set on sportswriting, Bryan Greenleaf couldn’t have imagined a career in an industry most people associate with numbers. An early position at UBS Financial Services, taken simply to gain some professional experience, revealed an unexpected appreciation for the role thoughtful planning can play in someone’s life. But perhaps even more unexpected was this: Bryan’s writerly instincts—not just finesse with numbers—would become his biggest asset as a financial planner. His ability to ask the right questions, establish comfortability for others to do the same, and a knack for clarifying the complex became his signature as he spent the next decade helping people create the life they envisioned.

Today, as Head of Advice+ Planning at Charter Oak Financial, Bryan leads the firm’s Wealth Management and Financial Planning teams, helping shape the strategy, resources, and infrastructure that support advisors as they grow and scale their practices. He works closely with advisors on advanced planning strategies, wealth management solutions, and practice development while driving initiatives that enhance both the advisor and client experience.

What continues to energize him most is the opportunity to help advisors succeed while advancing a profession he cares deeply about. He is endlessly curious about the evolving worlds of investing, wealth management, and financial planning, and believes the best leaders are those who remain humble, continue learning, and never stop asking questions.

Outside of work, Bryan enjoys spending time with his wife, Shannon, and their three dogs, Stella, Doug, and Duncan. When he’s not working alongside advisors, you’ll likely find him at the gym, on the golf course, outdoors whenever possible, or indulging his lifelong interest in all things automotive.