Job Description

Town Manager

The Town of Chestertown is currently seeking a Town Manager. Chestertown, founded in the early 1700s and still a thriving riverside college town with a large historic district, is regularly listed as one of the most charming communities in Maryland. With a population of 5,600, Chestertown is right-sized but eager for innovative growth. As the county seat of Kent County, it is an artistic, commercial and educational hub for the region. Chestertown is a really great place to live and work.

The Town Manager plays a pivotal role in the administration and management of town operations, ensuring that the community's needs are met effectively and efficiently. This position requires a dynamic leader with a strong background in business development, strategic planning, project management and finance. The Town Manager will oversee various departments, implement policies, and work collaboratively with town officials to foster growth and improvement within the community. The town employs thirty-six full-time employees.

Responsibilities

Lead and supervise town staff, ensuring effective performance and professional development. Develop and implement strategic plans to enhance town services and operations. Manage the town's budget ($4,500,000) and Utilities budget ($2,000,000) including profit loss analysis to ensure financial stability. Oversee business development initiatives to promote economic growth within the community. Design and facilitate process improvements to enhance operational efficiency. Coordinate with various departments to ensure alignment with town goals and objectives. Represent the town in meetings with stakeholders, residents, and external organizations. Plays a critical role in building trust and transparency between the town government and its residents. Responsible for overseeing financial management, coordinating special projects and managing municipal planning functions. Familiar with grant writing and overseeing grant opportunities. Prepare reports and presentations for the Town Council regarding operational updates and strategic initiatives. Responsible for maintenance of the Town's web site, social media and other communications assets in facilitating better communication with citizens. Consults and coordinates with the Town Attorney regarding legal matters; provides general guidance to him/her on Town policies and parameters established by the Town Council.

Qualifications

Proven experience in leadership roles, preferably in municipal management or related fields. Strong skills in business development, strategic planning and finance. Demonstrated ability to supervise staff effectively while fostering a positive work environment. Experience in project management with a focus on delivering results within established timelines. Excellent communication skills, both verbal and written, with the ability to engage diverse audiences.
Possesses skills in resolving disputes and complaints from citizens.

Knowledge of local government operations and regulations. A commitment to continuous improvement and innovation in service delivery. Bachelor's degree, preferably in public administration, business administration, urban planning, or closely related field. Master's degree in one of the above fields is considered a plus. Certified Public Manager is considered a plus. Previous experience as a Town Manager or Assistant Manager is strongly encouraged. Establishes and maintains effective working relationships with other Town employees, public officials, and citizens. Performs other duties assigned by the Mayor and Town Council.
This role is essential for driving the vision of the town forward while ensuring that all operations align with community values and objectives.

Job Type: Full-time

Pay: $120,000.00 - $130,000.00 per year

Benefits:

Maryland State Pension 401(k) Dental insurance Health insurance Vision insurance Life insurance Paid Vacation and Sick time Paid Holidays Tuition reimbursement in selected areas
Interested candidates should submit a cover letter, resume, salary requirements and professional references to Town of Chestertown, Attention: Human Resources, 118 N Cross Street, Chestertown, MD 21620 or by email to hr@chestertown.com. This position is open until filled; first review of applications will begin on

Monday, December 1st, 2025

.

For more information about the Town of Chestertown, please visit www.chestertown.gov.

The Town of Chestertown is an Equal Employment Opportunity Employer.

Job Type: Full-time

Pay: $120,000.00 - $130,000.00 per year

Benefits:

401(k) Dental insurance Health insurance Life insurance Paid time off Retirement plan Tuition reimbursement Vision insurance
Work Location: In person