Marblehead Chief Financial Officer Aleesha Benjamin is leaving in August after accepting the position of CFO for the town of Nantucket.
“Since joining Marblehead, Benjamin has played a pivotal role in modernizing the town’s financial operations and strengthening its long-term financial planning,” according to a statement from Town Administrator Thatcher Kezer Friday afternoon. “Her leadership has helped position the town with stronger financial management tools, greater transparency and improved organizational effectiveness while helping the town successfully navigate a period of significant fiscal challenges.”
Kezer announced last month that he is leaving Marblehead at the end of the year. Their departures means Marblehead is losing its two top administrators.

Here is more of Kezer’s Friday statement about Benjamin:
“Aleesha’s untiring work ethic, exceptional financial expertise, and commitment to public service have been instrumental in strengthening the town’s financial operations. She played a critical role in developing the detailed financial analyses that supported our annual budgets and Proposition 2½ override planning, ensuring that our decisions were based on sound data, careful forecasting and complete transparency.
“Beyond the numbers, Aleesha has led the transformation of our financial operations from largely paper-based processes to modern electronic financial systems that provide significantly greater transparency, more effective budget monitoring, improved financial reporting, and stronger long-range financial projections. These improvements have given town leadership, elected officials, department heads and residents better tools to understand and manage Marblehead’s finances while improving accountability throughout the organization.
“Aleesha has also been instrumental in strengthening Marblehead’s long-term financial position. Her disciplined approach to financial management, forecasting, and strategic planning has helped the town navigate difficult budget challenges while preserving essential municipal services. Her work was critical to developing the financial framework that supported the town’s successful Proposition 2½ override and established a sustainable path forward for the community.
“Through her leadership and dedication, Marblehead has maintained its coveted AAA bond rating despite the fiscal challenges facing municipalities across the Commonwealth. That achievement reflects not only sound financial policies but also the confidence that independent bond rating agencies continue to place in the Town’s financial management and long-term planning.
“In addition, Aleesha spearheaded the ongoing reorganization of the Finance Department, strengthening collaboration and efficiency across the Treasurer/Collector’s Office, Accounting Division, Information Technology Department, and Assessors Department. Her vision has created a more integrated organization that is better equipped to manage the increasingly complex financial and operational responsibilities of local government while positioning the Town for continued success.
“Aleesha has been a trusted advisor, an innovative leader and a valued colleague whose professionalism, integrity, and dedication have made a lasting impact on the town of Marblehead. Her leadership has established a strong foundation that will benefit the Town for years to come.
“On behalf of the town, I want to sincerely thank Aleesha for her outstanding service and wish her every success in her new role. She leaves Marblehead in a far stronger financial position than when she arrived, and her contributions will continue to benefit our community well into the future.”
Kezer said Bemjamin will work with town leadership in the coming weeks to ensure a smooth transition. The town will begin the recruitment process for her replacement immediately.
The Current has reached out to Select Board Chair Dan Fox and Finance Committee Chair Alec Goolsby for comment about Benjamin’s departure and what it will mean for Marblehead to lose its top two administrators.
