Experience

Michael joined UBS in 2010 after 24 years at Morgan Stanley Smith Barney and its predecessor firms beginning with EF Hutton in 1986 and holds the distinctive title of Senior Vice President. With almost 40 years of wealth management experience Michael has extensive experience in offering a variety of wealth management and planning based services for high-net-worth families. He is a Senior Portfolio Manager and has been a Certified Investment Management Analyst^® professional since 2002.

Michael is a graduate of the Isenberg School of Management at the University of Massachusetts in Amherst, and received his MBA at Suffolk University in Boston. Michael credits his successes to his children and partners at Winn Wealth Management; James and Jenna. Michael lives with his wife Annemarie in Reading, MA. He enjoys golf, skiing, music, cooking, and spending every spare moment on Cape Cod.

James brings over a decade of experience in financial services, with a focus on helping high net worth individuals, families, and business owners navigate the complexities of wealth. As a CPWA^® professional, CERTIFIED FINANCIAL PLANNER^® practitioner, and Certified Public Accountant (CPA), James integrates advanced financial planning with tax-aware portfolio construction to provide tailored, sophisticated strategies across investments, estate planning, exit planning, insurance and banking.

James joined Winn Wealth Management in 2020 after completing the UBS Wealth Planning Associate Program, where he honed his skills in holistic wealth strategy. He began his career in 2013 at Ernst & Young (EY) in the Financial Services Office, providing assurance and advisory services to clients in the banking, capital markets, and asset management sectors. It was there he earned his CPA and developed a deep understanding of financial structures and risk management.

James is a graduate of the University of Massachusetts Amherst, holding dual degrees: a Bachelor of Business Administration in Accounting from the Isenberg School of Management and a Bachelor of Arts in Economics from the College of Social and Behavioral Sciences.

James lives in Boston’s North End neighborhood with his wife Natalie and enjoys music, golfing, ice hockey, and spending time outdoors with friends and family.  

Jenna joined Winn Wealth Management in 2019 and serves as Head of Team and Client Operations. In this role, she works closely with both clients and her team each day, ensuring a seamless and personalized experience. With a deep understanding of client needs, Jenna is passionate about simplifying the complexities of wealth management, streamlining processes, and making life easier for others. She takes pride in building lasting relationships and helping clients fully realize the value of UBS resources.

Before joining Winn Wealth Management, Jenna spent five years at State Street Global Advisors. As part of the intermediary business group sales team, she covered ETFs and the ETF industry for institutional broker-dealers and advisors across the Northwest Coast. This experience gave her valuable, hands-on expertise in the financial industry and, in particular, wealth management solutions.

Jenna earned her Bachelor’s degree in Finance and Economics from Providence College in Providence, RI. She holds her Series 7 and 63 licenses while pursuing her Series 66.

Jenna married her husband Ty in June of 2024, and they live in Andover, MA. Outside of work Jenna enjoys running, snowboarding, golf, music, traveling, style, and spending time on Cape Cod.