Jen Jester

Jen Jester Business Lawyer New England

Attorney, Member of the Firm
Phone: 413-475-5120
Email: jjester@outsidegc.com


Jen Jester joined Outside GC in 2016, bringing a wealth of experience in commercial real estate.  Jen has managed a full array of real estate transactions, including leasing, acquisitions, dispositions, and re-financings, for a wide variety of investors and owners, landlords, and tenants.  Jen’s clients appreciate her ability to quickly and cost-effectively translate complex business terms into real world solutions.  She developed this skill by drafting and negotiating hundreds of leases, purchase agreements, mortgages, easements and other transaction-specific documents over the course of her nearly two decade-long legal career. Jen’s clients at Outside GC include, among many others, Alternative Compassion Services, Salsify, PandoLogic, Hillel International and Partnership for a Healthier America.

Throughout her career, Jen has also represented diverse corporate clients in connection with office, R & D, medical and industrial properties.  She has negotiated ground leases on behalf of real property owners, including hospitals, for development of medical office and other buildings.  She has drafted and negotiated leases with medical practice groups and solo practitioners, including provisions related to the disposal of medical and hazardous waste, ADA compliance, tenant improvement allowances for medical uses, and provisions designed to maintain the safe harbor from the Anti-Kickback Law for leasing transactions.

Jen began her commercial real estate career in 1999 at Choate, Hall & Stewart in Boston, where she managed leasing, purchase and sale, and other transactions for real estate investment and management firms, developers and institutional landlords.  Her clients included Archon Group (now Goldman Sachs Realty Management L.P.), Condyne Capital Partners, LLC, Cathartes Private Investments, and the Massachusetts Turnpike Authority (now part of the Massachusetts Department of Transportation).  Jen’s practice at Choate also included management of local, state and federal permitting for real estate projects including zoning review, environmental review (MEPA and NEPA), wetlands, waterways and historical and landmark preservation programs.  After Choate, Jen continued her real estate practice with Dionne & Gass in Boston (now part of Saul Ewing LLP), where she handled lease negotiations, purchase and sales agreements, mortgages, and other documents to close deals on behalf of real estate investment and management firms.

Prior to her legal career, Jen spent a decade working in several large technology companies, experience which enriches her legal work.  With Boston-based PR firm Lois Paul & Partners, she managed numerous high tech accounts, including Sybase, Inc. and Lotus Development Corporation (later bought by IBM).  At Banyan Systems, then a $100 million manufacturer of networking software, Jen managed a team of communications professionals and a multi-million-dollar budget dedicated to media, analyst and investor relations, advertising, event planning, and marketing publications.  

Jen is a cum laude graduate of Boston College Law School.  Prior to her law degree, she obtained bachelor’s and master’s degrees from Florida State University in marketing communications.  She also served as an elected member and Chair of the School Committee in Longmeadow, Massachusetts, where she currently lives with her daughter and a house full of rescue pets.