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With over 20 years of experience at both law and accounting firms, Jeff’s practice focuses on all areas of federal and state taxation, with an emphasis on domestic and international tax structuring, contractual matters, planning, corporate transactions – mergers and acquisitions, real estate, and partnership formations. He has a broad background in federal income tax law and provides tax advice in Internal Revenue Service and state tax controversy matters, drawing on his experience as an IRS District Counsel.

Jeff represents clients on both the buy-side and sell-side in several hundred taxable and tax-free transactions ranging from $5 million to $6 billion. Within the real estate industry, his experience includes joint ventures and fund formation, supporting multiple property types including hospitality, homebuilders, military housing, and multi-family.


Work Experience

  • Hinckley Allen
    • Partner (2019-Present)
    • Associate (2003-2005)
  • Gesmer Updegrove
    • Partner (2011-2015, 2016-2019)
  • EY
    • Tax Transaction Adviser (2015-2016)
  • Greenberg Traurig
    • Associate (2005-2011)


  • Former Certified Public Accountant (CPA)
    • Massachusetts
    • Wisconsin

Professional Affiliations

  • American Bar Association
  • Boston Bar Association
  • Massachusetts Society of Certified Public Accountants
  • Wisconsin Institute of Certified Public Accountants

Bar Memberships

  • Massachusetts
  • Wisconsin
  • United States District Court, Eastern Wisconsin
  • United States Tax Court, Massachusetts

News & Insight


How Businesses Can Convert Real Estate into Cash and Continue to Operate at the Property

June 30, 2020

The impacts of COVID-19 on businesses are being felt across industries and around the globe. The impacts to many US businesses have been profound and quick access to cash has become of critical importance to many companies. At the same time companies’ ca…


Tax Breaks and Benefits for Businesses Impacted by COVID-19

April 1, 2020

The pandemic of COVID-19 has drastically impacted the United States economy. Over the past few weeks, federal legislation has quickly been enacted to help stimulate the economy and provide much needed cash flow to individuals and businesses. In this alert,…


Qualified Opportunity Zones: What We Know From New Regulations

July 16, 2019

Interest continues to increase in a promising new program contained in the 2017 Tax Cuts and Jobs Act, which provides significant tax incentives for investors in Qualified Opportunity Zones (QOZ).After releasing the first set of QOZ proposed regulations on…

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Firm News

Hinckley Allen Welcomes New Corporate & Business Attorney Jeff Groshek

March 8, 2019

Hinckley Allen is pleased to welcome Jeff Groshek as Partner to the Firm’s Tax Group. Jeff is a seasoned tax attorney with over 20 years of experience at both law and accounting firms. Jeff is a graduate of Boston University School of Law, where he earne…

Case Study

Hinckley Allen Facilitates Brinker Capital Merger in Significant Moment for Financial Services Industry

Hinckley Allen represented its long-time client, Brinker Capital, a registered investment adviser, and its affiliated broker-dealer, in their sale to new investment partnership controlled by funds affiliated with Genstar Capital Partners, a California-base…


Past Event

Guide to Opportunity Zones in Massachusetts

June 19, 2019

Jeff Groshek and Leah C. Rubega will discuss "Opportunity Zones: How they work and what will be the winning process in Massachusetts?" at the Realtors Commercial Alliance of MA June Meeting. Commercial real estate professionals will be provided with an upd…

Past Event

The Land of Oz (Opportunity Zones)

March 22, 2019

John H. Sokul, Jr. and Jeff Groshek join the Arnett Development Group's (ADG) and New Hampshire Commercial Investment Board of Realtors (NHCIBOR) panel on "The Land of Oz (Opportunity Zones) to help attendees to understand the Qualified Opportunity Zone pr…