Thomas N. O’Connor, ESQ.


Tom O’Connor is the President and a founder of Baystate Wealth Management, LCC.

As President, Tom is charged with overseeing and developing the business and is involved in the day-to-day activities of the company, including setting investment policies. Tom is licensed as an investment advisor representative and as a financial representative for life and health insurance products.

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In March 2000, after nearly 30 years of practicing law, Tom retired from Hale and Dorr of Boston, MA to co-found a federally registered investment advisory firm, which he sold in October 2008. Shortly thereafter, Tom joined Baystate and began assisting with the firm as it built out its wealth management platform. Tom was named President of Baystate Wealth in October 2009.

Tom graduated cum laude from St. Lawrence University in 1975. While at St. Lawrence, Tom was one of the starting goaltenders for the hockey team and an officer of Beta Theta Pi Fraternity. After a brief stint with a minor hockey team, Tom went to the Albany Laws school of Union University, where he was the Editor of the Albany law review, graduating cum laude and a member of the Justinian Society.

Tom lives in Boston, MA with his wife Julie. They have two sons who graduated from Colgate University and St. Lawrence University. Tom is an avid golfer, skier, and sailor. He served on the Board of the Baystate Financial Charitable Foundation, as Chairman of the Board of Tower School in Marblehead, coached youth lacrosse in Swampscott/Marblehead and is active with the Friends of Special Olympics on the North Shore and with the ALS Association Massachusetts Chapter.

John Cogswell, CFA

Portfolio Manager/Chief Market Strategist

John Cogswell is the Chief Market Strategist for BWM, a member of the Investment Committee, and a Senior Portfolio Manager.

John began his career in the financial service industry in 1995. Prior to Joining BWM, John was a Senior Vice President at Korben Insight Management, an E*Trade Wealth Management company. Earlier in his career, John was an investment manager at A.G. Edwards, and a registered representative at Gruntal & Co.

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After graduating from Northeastern University, John joined Gruntal & Co to construct portfolios of smaller to mid-sized companies using the firm’s proprietary research for retail clients. At A.G. Edwards, he managed portfolios of equities incorporating hedging strategies with exchange-traded options. While at E*Trade Wealth Management, John served as a member of the firm’s investment committee.


John joined BWM as a Portfolio Manager in 2009. He was promoted to Chief Market Strategist in 2012. John holds FINRA Series 7, 63 and 65 licenses.


John received a Bachelor’s of Science, with a dual major in Finance and International Finance, from Northeastern University in 1995.  John is an avid skier and enjoys traveling to foreign countries such as Ireland, Iceland, and Mexico and the islands.

John Cogswell

Joshua Pierce, CFP®, CAIA

Director of Research | Portfolio Manager

Joshua Pierce serves as the Director of Research and Portfolio Manager for BWM.  He is a member of the Investment Committee and a Senior Portfolio Manager. Since 2001 Josh has been working with high net worth individuals, companies, trusts and Foundations within the investment and financial services industry.

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Before Joining BWM in 2009, Josh held the position of Vice President with E*TRADE Wealth Management. Prior to that, Josh held the position of Financial Advisor with both UBS Financial Services, Inc. and the Private Clients Group of Fleet National Bank (now Bank of America)

In his time with E*TRADE Wealth Management, with the assistance of the firm’s investment committee, Josh’s helped determine investment strategy and asset allocation for a number of E*Trade’s existing and prospective clients. At UBS Financial Services, Josh worked with his clients on investment strategies ranging from short-term municipal bonds to customized managed portfolios. During his time with Fleet, Josh’s primary focus was on investment strategies and bank products aimed at offering principal protection and income to his clients.

Josh earned his MBA from Northeastern University’s D’Amore-McKim School of Business and received his undergraduate degree from Wheaton College in Norton, MA. Josh holds the distinguished Certified Financial PlannerTM (CFPÒ) and Chartered Alternative Investment Analyst (CAIA®) designations. Josh lives in Brookline with his wife, Caroline, and their three boys.  Josh is an avid golfer, skier and coach for his sons’ teams

Joshua Pierce

Greg Pinto, CFP®

Chief Executive Officer

Gregory J. Pinto is the Chief Executive Officer for Baystate Wealth Management. Greg provides innovative investment management, generational planning and wealth transfer solutions through a comprehensive and coordinated approach for his clients.

Greg provides a focused service for high-net worth individuals, successful professionals and business owners. Greg brings a fresh perspective to investment strategies backed by over two decades of experience.

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He began his career in the financial services industry in 1991. Prior to joining BWM, Greg Managing Associate of New England Financial Services in Rochester, NY.

Greg received an MBA in Finance and Public Accounting from the William E. Simon School, University of Rochester in 1989 and his Certified Financial Planner designation in 2001. He is a member of the Inner Circle of Advisors at the MetLife Dealer Group and has been recognized as a member of the “Top of the Table” by the Million Dollar Round Table.

Greg Pinto

Jill Ledgewood

Chief Compliance Officer

Jill Ledgewood is the Chief Compliance Officer of Baystate Wealth and a member of the Investment Committee. She began her career in the financial services industry in 2000 working at Boston Financial Data Services and joined Baystate Financial Services shortly afterwards in August of 2000 where she has worked in compliance for over 15 years. Jill is a registered principal and holds FINRA Series 7, 24 and 66 licenses.

Born in 1979, Jill received an Associate’s Degree in Business Management from Aquinas College in Milton, Massachusetts.

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Ethan Somers, CFA


As an analyst at BWM, Ethan contributes directly to the construction and implementation of various investment strategies. Ethan also works very closely with advisors, assisting with the analysis, development, and implementation of client investment solutions. He is an active and voting member of the Investment Committee, contributing his own personal research on the capital markets and insights into relevant geopolitical events.


Ethan delivers broad market, portfolio level, and asset-class level research to help advisors and clients better understand the drivers of risk and reward within various investment strategies.


Ethan has been working in the Financial Services industry since 2011. He began his career at a Boston-based private wealth management firm, servicing high net worth and institutional clients around the world. Ethan joined Baystate Financial in 2012, helping Financial Advisors identify investment solutions on behalf of their clients. In 2013, Ethan transitioned to the Investment Department at Baystate Financial and rose to the role of Agency Director Investment Specialist, before joining BWM in 2016.


Ethan graduated from the University of Denver’s Daniels College of Business in 2011 with a Bachelor of Science in Business Administration (BSBA), a major in Finance and minor in International Studies. Ethan is CFA® charterholder, and passed all three levels on his first attempt. He resides in Boston and is a native of the North Shore of Massachusetts.

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Ehan Summers

Stuart Long, CFA

Head Trader, Analyst

Stuart is an active participant and voting member of the Investment Committee.  As the Head Trader for Baystate Wealth, he is tasked with the implementation and execution of the portfolio strategies approved by the Investment Committee.


As a Portfolio Analyst, Stuart works with advisors and their clients to determine and build an asset allocation based on the client’s unique needs.  Additionally, Stuart provides timely research to the investment committee on current trends in capital markets and fundamental valuations of global market segments.


Prior to joining BWM in 2012, Stuart held several positions at USB Wealth Management, most recently as a Branch Analyst supporting Financial Advisors with client engagement and retention.  He assisted with all aspects of the of the client process, including the creation of financial plans, asset allocation, manager search and selection, portfolio construction, and strategy reviews.


Stuart is a CFA® charterholder.  He graduated from the University of Maryland, College Park, with a B.A. in Economics in 2004.  He relocated from his hometown, Kensington Maryland, to the Boston area in 2008.  He now resides in Woburn, with his wife Katherine, and their daughter.

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Stuart Long

Josh Mayo

New Business Manager

Josh Mayo serves as point of contact for all operational issues with advisors, clients, custodians and broker dealers. He is responsible for new account submissions as well as all account maintenance. He is also in charge of all money movement into BWM, including tracking transfers and money movement between managers and various accounts.

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Before joining Baystate Wealth, Josh worked for Commonwealth Financial Network for more than four years as an Operations Priority Specialist where he supported all areas of operations including General Investigations, Transfer of Assets, Retirement Operations, New Accounts and Cashiering departments. Josh previously worked with Commonwealth as a New Accounts Associate.

Josh holds Bachelor of Science Degrees from in Business Management, Finance, and Psychology from Roger Williams University in Bristol, RI. In addition, Josh is a FINRA Series 7 license holder.

Josh Mayo

Nicholas P. Neff

Client Relationship Liaison

Nick is a Client Relationship Liaison at BWM, assisting advisors and clients with all aspects of operations including the movement of assets, account opening, answering inquiries concerning operational issues, and more.

Prior to joining BWM, Nick worked at State Street as a Private Equity Fund Administrator, and before that, he worked at Wellesley Investment Partners in Wellesley, MA.

Nick has a Bachelor of Science Degree in Business Administration from the College of Charleston in South Carolina. In his free time, Nick enjoys fishing and traveling.”

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Nick Neff