Experience You Can Trust
Jennifer Ann Macksey is the daughter of Teresa (Casuscelli) and the late Edward J. Macksey. She was educated locally, attending East School, Conte Middle School, and Drury High School. Life changed for Jennifer when her father passed in 1986, and she became more focused on helping her family with their business and saving money for college rather than being a teenager. Early on in life, she developed a strong work ethic which is evident today through her work style.
Jennifer’s strong leadership and fortitude to get the job done— and done right— is perhaps the hallmark of her career.
Jennifer is a caring, effective leader who listens, researches, and collaborates until a sound pathway is established for all projects. Jennifer prides herself on the relationships she has formed with both her colleagues and her students. While at MCLA and SVC, Jennifer supported students as an administrator, instructor, and mentor; always focusing on the personal and academic growth of her students. Jennifer has proven time and time again that she cares about the people she serves.
Jennifer Macksey will bring 28 years of professional municipal and educational experience and knowledge to City Hall. She will lead with diplomacy, respect, professionalism, and most importantly, Jennifer will always act in the best interest of the City of North Adams.
View full resume- Early career
Director of Finance & Chief Procurement Officer
After graduating from Drury High School, Jennifer earned a B.S. in Accounting and Business Administration from Trinity College in Burlington, Vermont. During summer breaks she worked in various capacities for the City of North Adams, including the Department of Public Services. Upon graduation, at age 22, she was appointed full-time Director of Finance and Chief Procurement Officer.
- 2000
Treasurer/Tax Collector & Chief Financial Officer
Appointed Treasurer/Tax Collector and Chief Financial Officer for the City of North Adams.
- 2008
Massachusetts College of Liberal Arts
Joined MCLA as Director of Student Accounts and served as part-time faculty teaching accounting and economics. She was also known as the team mom for the Men’s basketball team.
- 2013
Master’s in Higher Education Administration
Earned her Master’s Degree in Higher Education Administration from Baypath College.
- 2015–2019
Executive Vice President, Southern Vermont College
Served as Executive Vice President of Southern Vermont College until 2019.
- Today
Assistant Superintendent of Operations & Finance
Currently serves as Assistant Superintendent of Operations & Finance for the North Berkshire School Union.


