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Why Boston-based Middle Market Companies Must Plan for the Great Wealth Transfer

May 14, 2026 Gary Pirri, New England Market Executive at Wells Fargo Commercial Banking

For many Boston-based middle market companies, coordinating business and personal financial planning is increasingly relevant, especially as many family-owned companies consider transitions in ownership. Whether you’re an outgoing CEO of a local real estate development firm[1], the leader of a robotics company[2] or a large outdoor retailer[3], there are many examples of leader transitions and succession plans happening in real time in Boston and throughout New England today.

According to recent data[4] from the National Center for the Middle Market (NCMM), 17% of U.S. middle market companies (as defined by NCMM as companies with annual revenue between $10 million to $1 billion) are considering ownership transfers over the next 24 months. Additionally, one-third of these businesses are multigenerational family businesses. The Great Wealth Transfer of $124 trillion[5] from the Baby Boomers to heirs will only accelerate this handoff of wealth even faster.

Given its strong founder-led culture and large number of knowledge-based firms, Boston is ripe for succession planning risk. Research[6] from the City of Boston Planning Department shows that as of 2025, the city’s Professional, Scientific, and Technical Services sector includes approximately 100,644 employees and 5,619 establishments, amounting to 14.7% of all employment, 17.8% of businesses, and 20.3% of Gross City Product (GCP). These industries range from computer systems design, scientific research, legal, accounting, architects, engineers, public relations agencies, and more. All these companies need to prepare for leadership transitions sooner rather than later.

If business owners don’t act now, they can face potential challenges involving employee turnover, stalled growth, and decreased company value. This could also have an impact on your reputation in the marketplace.

As businesses determine their next steps, here are a few tips to keep in-mind:

1. Have a Liquidity Plan

Even if you don’t plan to sell your business soon, have a plan in place. Make sure your successor has access to liquidity to meet any ongoing financial obligations. Business owners should get familiar with the Massachusetts estate tax[7] filing threshold, as there have been changes since 2023 and transitions typically yield substantial liquidity that will be impacted by these thresholds.

2. Consider Your Options

Outright sale to a strategic third party. Private Equity.  Generational transition or an ESOP.  The State of Massachusetts has a dedicated Center for Employee Ownership[8] that provides information and resources on employee ownership if that is a direction you decide to go. This is an arrangement in which a company’s employees own shares in the company’s stock. Popular options include Employee Stock Ownership Plan (ESOP) companies and Worker Cooperatives (Co-ops). This is not only a key tool in business succession planning, but it’s a policy priority in the state that Boston businesses can take advantage of.

3. Talk to Your Trusted Advisors to Gain Perspective

This could be your banker, CPA, attorney, financial/wealth advisors, or professional coach. These are once in a lifetime decisions that require careful planning for them to be executed well.

In this environment, it’s important to stay nimble and be ready to take advantage of strategic business opportunities, while understanding and being prepared for the potential impact on the business and personal side of the balance sheet. Having a solid plan in place will differentiate the business owners that plan for success and ones that stumble.

__________

Disclaimer: The information provided herein is for informational purposes only and does not constitute legal or tax advice. Consult with your professional.

[1] The Davis Companies Announces Completion of Succession Plan with Elevation of Stephen David to CEO. Source: Company press release, March 26, 2026.
[2] CEO of Boston Dynamics to Step Down, as Hyundai’s Robot Strategy in Focus. Source: Reuters via U.S. News and World Report. February 11, 2026.
[3] L.L. Bean President and CEO Stephen Smith Plans Departure in 2026 After a Decade of Leadership. Source: Company press release, July 14, 2025.
[4] Year-End 2025 Middle Market Indicator. Source: National Center for the Middle Market, 2025.
[5] Cerulli Anticipates $124 Trillion in Wealth Will Transfer Through 2028. Source: Cerulli Associates website press release, December 5, 2024
[6] Industry Profiles 2025: Professional, Scientific, and Technical Services in Boston. City of Boston official website.
[7] Massachusetts Estate Tax Guide. Source: Massachusetts Department of Revenue
[8]  Massachusetts Center for Employee Ownership. Source: Massachusetts Office of Business Development

Meet the Author

Gary Pirri is the New England Market Executive within the Northeast Division of Wells Fargo Commercial Banking. Based in Boston, Gary leads teams focused on serving the financial needs of business banking and middle market customers throughout New England.

Gary has more than 30 years of banking experience, all of it working with middle market and business banking companies. Prior to joining Wells Fargo in 2008, Gary managed the New England Middle Market Commercial Banking business of LaSalle Bank, and has also held a variety of management positions with Fleet and its predecessor banks.

Gary earned his bachelor’s degree, with a double major in accounting and management, from Providence College, where he graduated magna cum laude. He went on to earn his M.B.A. at Providence College as well. Involved in a variety of professional and community organizations throughout his career, Gary currently sits on the board of The Sports Museum.

Born and raised in Rhode Island, Gary and his wife, Kathleen, now reside in Marshfield, Massachusetts. They have three children, sons Jake and Ben, and daughter Emma.

Connect with Gary

Gary A. Pirri Headshot
Gary A. Pirri

New England Market Executive, Commercial Banking Northeast Division

Wells Fargo & Company

Email Gary A.

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