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Mike Chesebro
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Mike Chesebro

Client Engagement Lead
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Mike is a Client Engagement Lead at F2 Strategy with more than 20 years of experience in wealth management and financial services technology. He specializes in helping wealth and trust organizations modernize their platforms, operating models, and client experience. Mike works closely with executive teams to navigate complex transformation initiatives, providing clarity on current-state challenges while helping define practical, actionable paths forward.

Mike brings deep expertise at the intersection of business strategy and technology. He is known for his ability to simplify complex environments and help organizations align technology investments with operational and client service objectives. His experience spans large-scale platform modernization, data and reporting transformation, private asset capabilities, risk management, and governance initiatives.

Prior to joining F2 Strategy, Mike spent 18 years at Brown Brothers Harriman, where he served as Head of Wealth Management Technology. In this role, he led a global team of more than 40 professionals and oversaw a multi-year transformation focused on scalability, data and reporting modernization, and enhancing private asset capabilities. He also led Compliance and Risk Technology, driving enterprise initiatives across anti-money laundering (AML), risk management, and data governance.

Earlier in his career, Mike held roles with State Street Wealth Manager Services and Putnam Investments. He is based in Duxbury, Massachusetts and enjoys spending time with his family, traveling, boating, and golfing.

Previous Experience
  • Brown Brothers Harriman
  • State Street Wealth Manager Services
  • Putnam Investments
Up Close with
Mike

What would you tell someone just starting out in the industry right now?

Focus on understanding how the business actually works before jumping to solutions. The people who stand out are the ones who can connect technology to real operational and client outcomes. Also, stay curious as this industry is evolving quickly, and those who continuously learn will have the biggest impact.

What do you think WealthTech will allow advisors to do in five years that they can’t do now?

Advisors will have a truly unified view of their clients across all assets, both public and private, with real-time insights and less reliance on manual processes. More importantly, technology will remove much of the operational burden, allowing advisors to spend more time on planning, relationship management, and delivering personalized advice at scale.

What are you most passionate about in your role at F2 Strategy?

I enjoy helping clients work through complex challenges and turning them into clear, actionable paths forward. Many organizations know where they want to go but struggle with how to get there. Being able to bridge that gap by connecting strategy to execution is what I find most rewarding.

Mike Chesebro
Back to Team

Mike Chesebro

Client Engagement Lead
Email IconLinkedIn Icon

Mike is a Client Engagement Lead at F2 Strategy with more than 20 years of experience in wealth management and financial services technology. He specializes in helping wealth and trust organizations modernize their platforms, operating models, and client experience. Mike works closely with executive teams to navigate complex transformation initiatives, providing clarity on current-state challenges while helping define practical, actionable paths forward.

Mike brings deep expertise at the intersection of business strategy and technology. He is known for his ability to simplify complex environments and help organizations align technology investments with operational and client service objectives. His experience spans large-scale platform modernization, data and reporting transformation, private asset capabilities, risk management, and governance initiatives.

Prior to joining F2 Strategy, Mike spent 18 years at Brown Brothers Harriman, where he served as Head of Wealth Management Technology. In this role, he led a global team of more than 40 professionals and oversaw a multi-year transformation focused on scalability, data and reporting modernization, and enhancing private asset capabilities. He also led Compliance and Risk Technology, driving enterprise initiatives across anti-money laundering (AML), risk management, and data governance.

Earlier in his career, Mike held roles with State Street Wealth Manager Services and Putnam Investments. He is based in Duxbury, Massachusetts and enjoys spending time with his family, traveling, boating, and golfing.

Previous Experience
  • Brown Brothers Harriman
  • State Street Wealth Manager Services
  • Putnam Investments
Expertise
Up Close with
Mike

What would you tell someone just starting out in the industry right now?

Focus on understanding how the business actually works before jumping to solutions. The people who stand out are the ones who can connect technology to real operational and client outcomes. Also, stay curious as this industry is evolving quickly, and those who continuously learn will have the biggest impact.

What do you think WealthTech will allow advisors to do in five years that they can’t do now?

Advisors will have a truly unified view of their clients across all assets, both public and private, with real-time insights and less reliance on manual processes. More importantly, technology will remove much of the operational burden, allowing advisors to spend more time on planning, relationship management, and delivering personalized advice at scale.

What are you most passionate about in your role at F2 Strategy?

I enjoy helping clients work through complex challenges and turning them into clear, actionable paths forward. Many organizations know where they want to go but struggle with how to get there. Being able to bridge that gap by connecting strategy to execution is what I find most rewarding.

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