Let’s Get Started!

Jennifer M. Cunningham


Waltham, Massachusetts
Direct Line:
Main Line:
617-523-1555 Ext. 1911
Toll Free Line:
Main Fax:
Direct fax:

Jennifer M. Cunningham joined Cushing & Dolan, P.C. in 2015 with over 13 years of estate planning and elder law experience as a paralegal. Jennifer is currently a Law Clerk in the Estate Planning Group of Cushing & Dolan assisting attorneys in drafting estate planning documents with a focus on eliminating estate taxes, avoiding probate, and protecting assets from long term care costs. She is also responsible for assuring that the paperwork necessary to fund trusts is provided and that plans are implemented in accordance with the terms provided under the engagement letter. From 2015 through 2018 Jennifer assisted clients with their Medicaid long-term care applications, long-term care asset protection planning using various strategies including Medicaid Irrevocable Trusts, Annuities and Pooled Trusts.

Prior to joining Cushing & Dolan, P.C., Jennifer worked at an elder law and estate planning law firm assisting attorneys in daily functions relating to estate planning and long-term care planning. There she was responsible for drafting of estate plans for clients, preparing guardianship/conservatorship petitions, probate petitions, inventories, and accounts. Jennifer was also previously with an estate planning law firm in Newton, for 8 years, where she handled the preparation of income, gift, estate and fiduciary tax returns, as well as drafting Wills, Irrevocable Life Insurance Trusts, Revocable Trusts, Wills, Durable Powers of Attorney HIPAA Releases, Advance Directives and ancillary estate planning documents. Jennifer also served as the firm’s administrator, handling human resources, billing and training new employees. She is a Massachusetts Notary Public.

Jennifer is currently pursuing her Juris Doctorate in the evening. Jennifer earned a B.S. in Business, magna cum laude, from Bay Path University.

Professional Associations:

Massachusetts Notary Public


Bay Path University, BSBA, magna cum laude