Town of Cheshire, Massachusetts

 Job Announcement

 Chief of Police

The Town of Cheshire, Massachusetts is seeking a highly qualified and experienced law enforcement professional to serve as its next Police Chief. This leadership role offers the opportunity to deliver effective, community-oriented public safety services while fostering trust, accountability, and strong relationships with residents. The selected candidate will have the unique opportunity to serve as a working Police Chief, working hand in hand with community members and department personnel to address local needs in a visible, hands-on leadership capacity. The ideal candidate will bring proven supervisory experience, sound judgment, and a collaborative leadership style, along with a commitment to upholding the highest standards of integrity and professionalism in policing.

COMMUNITY

Located in Berkshire County, Massachusetts, Cheshire is a close-knit community known for its rich history, scenic beauty, and strong civic spirit. Famous for the historic “Mammoth Cheese” presented to President Thomas Jefferson, Cheshire today is recognized for its rural character, welcoming neighborhoods, and exceptional outdoor resources, including the Appalachian Trail, Cheshire Reservoir, and Ashuwillticook Rail Trail. Residents value the town’s tradition of community involvement, public safety, and quality of life, making Cheshire an attractive place to live, work, and serve.

Cheshire is a town that values its past while investing in a safe and vibrant future. It's an ideal setting for leaders who value tradition, service, and authentic community connection.

To learn more about Cheshire, please visit https://cheshire-ma.gov

THE CANDIDATE

The next Chief of Police must be approachable, visible, and deeply engaged with the community. The successful candidate will actively connect with residents and stakeholders in both formal and informal settings, building strong partnerships and encouraging open dialogue.

As a key member of the Town’s leadership team, the Chief of Police will be a collaborative leader with demonstrated executive experience, exceptional communication skills, and a strong commitment to public safety and service. The Chief of Police must be responsive, empathetic, and capable of addressing the needs and concerns of an informed and engaged community. The candidate models the highest level of personal and professional integrity.

The ideal candidate will also bring:

• Significant law enforcement experience, including command-level leadership.
• A commitment to community policing and public engagement
• Strong decision-making, interpersonal, and organizational leadership skills
• A history of ethical leadership and professional development of staff

THE ROLE

The Police Chief is appointed by the Select Board and works under the policy direction of the Town Administrator and the Select Board. The Chief is responsible for the overall administration, leadership, and day-to-day operations of the Cheshire Police Department.

The Chief will set clear strategic goals, lead with vision, and foster a culture of accountability, professionalism, and service. This role includes, but is not limited to, planning and directing all internal and external departmental functions related to the enforcement of local, state laws, and federal laws. Key responsibilities include providing motivational leadership, overseeing training and professional development, preparation and administration of department budgets, ensuring succession planning, and guiding staff at all levels.

The Chief of Police will be expected to participate actively in public events, outreach initiatives, and community-building efforts, while also responding to inquiries, complaints, and grievances with promptness, fairness, and professionalism.

THE DEPARTMENT 

The Cheshire Police Department is dedicated to delivering both traditional and non-traditional law enforcement services to residents and visitors alike. The Department operates with a strong emphasis on compassion, integrity, and ethical conduct, ensuring that every interaction reflects the values of the community it serves.

The Cheshire Police Department is a full-service agency consisting of two full time patrol officers with planned growth for one additional officer, dependent on upcoming town meeting. The Police Chief will also oversee a shared animal control officer.   

RECOMMENDED QUALIFICATIONS 

• Bachelor’s Degree in Law Enforcement, Criminal Justice or related field. Familiarity and experience with community-oriented policing process; or an equivalent combination of education and experience. Graduates of major policing executive development programs including FBI National Academy, Police Executive Research Forum Senior Management Institute for Police or Police Executive Leadership Institute, and FBI LEEDA are encouraged to apply.
• Experience: A minimum of ten (10) years’ experience in law enforcement, with at least three (3) years in a significant command or supervisory capacity.
• Candidates must be active in the Law Enforcement field and hold a minimum rank of sergeant to apply. Any equivalent combination of education and experience may also be considered. 
• Possession of or ability to obtain a valid Massachusetts driver's license. 
• Must have a valid Massachusetts Firearms License or the ability to obtain one upon hire.
• Applicants must graduate from the Commonwealth of Massachusetts Municipal Police Training Committee (MPTC) Basic Recruit Officer Academy (or eligible for a Permanent Exemption by the MPTC). They must satisfy all requirements set forth by the Massachusetts Peace Officer Standards and Training Commission for certification as a Police Officer in the Commonwealth of Massachusetts.

COMPENSATION & BENEFITS

Cheshire offers a competitive compensation and benefits package, with a salary range of $95,000 to $110,000, commensurate with qualifications. Benefits include group health and dental insurance, as well as an optional employee-paid supplemental health plan. The Town provides a $10,000 life insurance policy for police personnel, along with paid vacation, holidays, personal leave, and sick time.

Interested applicants should email a cover letter and résumé as a single PDF file to Public Safety Consultants, LLC at [email protected]. Cover letters and resumes should be received by 10:00 A.M. on Thursday, June 11^th, 2026.

The Town of Cheshire is an Equal Opportunity Employer.