Jennifer M. Cunningham

Waltham, Massachusetts
(617) 523-1555
(617) 523-5653

Jennifer Cunningham joined Cushing & Dolan, P.C. in 2015 with over 13 years of estate planning and elder law experience as a paralegal. She is currently working in the Elder Law group of our firm’s Estate Planning department assisting attorneys with document preparation, and assisting 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, for 5 years, 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 earned a B.S. in Business, magna cum laude, from Bay Path University.


  • Bay Path University, BSBA, magna cum laude

Professional Associations

  • Massachusetts Notary Public

Past Employment Positions

  • Lannik Law, LLC, Paralegal and Firm Administrator
  • Mendel & Associates, Paralegal and Firm Administrator