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Assistant Superintendent Human Resources

Middlesex Sheriff's Office
Woburn, MA Full Time
POSTED ON 5/1/2026
AVAILABLE BEFORE 10/25/2026
The Middlesex Sheriff’s Office (“MSO”) is seeking a qualified professional for the position of Assistant Superintendent / Human Resources (“Assistant Superintendent”) to work as part of the senior management team in the MSO’s Administrative Office, located in Woburn, MA.  Under the direct supervision of the Special Sheriff, the Assistant Superintendent is responsible for the overall day-to-day operation of the MSO’s Human Resources Division (“HRD”).  The Assistant Superintendent will be a strategic and proactive human resources expert who has exceptional operational strengths and offers strong organizational leadership.  The hours of work will be 8:00a.m. to 6:00p.m. flex, Monday through Friday.  The Assistant Superintendent will be required to respond to any HRD needs when required and depending on the needs of the MSO. The hours of work and days off are subject to change and based on the discretion of management.  This is a full-time, exempt, at-will employment position.

Additional responsibilities of the Assistant Superintendent include, but are not limited, to the following
  • Responsible for supervising and managing all employees within the HRD and payroll department;
  • Developing, implementing, evaluating and advising all MSO employees on human resources policies and procedures;
  • Ensuring all HRD programs are based upon the goals and objectives of the MSO while meeting standards set forth in organizational policies and procedures, as well as those set by the American Correctional Association (“ACA”) and Massachusetts Department of Corrections (“DOC”) regulations;
  • Supervising and working in conjunction with the Assistant Human Resources Director and Payroll Director to ensure the sound day-to-day operation of the HRD and payroll department;
  • The Assistant Superintendent must ensure there is consistent engagement with the Chief Financial Officer (or their designee) regarding the forecasting, monitoring and reporting of all payroll expenditures at the MSO;
  • Responsible for overseeing new employee recruitment, orientation and training, and also working with MSO management and employees on training and performance evaluations;
  • Ensure that all employment positions are prepared for both internal and external posting; 
  • Facilitation of promotional examinations in conjunction with collective bargaining agreements;
  • Overseeing the hiring/onboarding process for new employees, including but not limited to entrance examinations, background investigations, interviews of new employees, processing all required federal and state employment forms;
  • Maintaining confidentiality and security of employee information; including personnel, medical and discipline files;
  • Overseeing the processing of all employee health/dental/vision/life insurance benefits;
  • Managing all employee leave benefits, including but not limited to, federal and state authorized employee leave as well as employee leave subject to collective bargaining agreements and MSO policy and procedure.  Employee leave benefits include, but are not limited to: accrued vacation, sick, personal, compensation, Family Medical Leave Act (“FMLA”); Paid Family Leave Act (“PFML”); Small Necessities Leave Act (“SNLA”); Massachusetts Earned Sick Time (“EST”); Military Leave; Domestic Violence Leave and; Maternity/Paternity Leave;
  • Supervising and working in conjunction with the Americans with Disabilities Act Coordinator on all facets of the MSO’s reasonable accommodation process;
  • Overseeing employee industrial accident claims and associated benefits;
  • Supervising and working closely with the MSO Peer Support Coordinator and the MSO’s licensed professional Employee Assistance Provider (“EAP”) vendor;  
  • Acting as the MSO’s Diversity and Harassment Prevention Officer.  Responsible for investigating and addressing all employee complaints;
  • Ensuring any required reporting for human resources and/or payroll are developed and submitted in a timely and accurate manner;
  • Assisting all MSO employees as they navigate through the retirement process with the State Board of Retirement.  Also, assisting current retirees with any questions or issues they may have regarding their retirement benefits;
  • Responsible for negotiating collective bargaining agreements, in addition to any impact bargaining requirements with multiple unions;
  • Ensuring strong labor relations with all bargaining units by responding to union grievances and assisting the legal department with arbitration proceedings, including drafting responses and testifying when necessary;
  • Drafting and issuing employee discipline in accordance with MSO Policy and Procedure and applicable collective bargaining agreements; 
  • Updating and maintaining MSO staffing analysis and organizational charts;
  • Maintaining strong communication and working relationships with facility administration, correctional personnel, contracted providers, and outside agencies;
  • Evaluating and recommending methods of improving operational efficiency and cost effectiveness;
  • Facilitating routine meetings with human resources and payroll team members to ensure effective communication with staff on all shifts;
  • Performing and/or assisting in all other duties as required by the Special Sheriff (or designee).
Working Conditions:
The individual selected for this position must be cognizant of the confidential and sensitive nature of a 24/7 law enforcement agency.  Must comply with all institutional rules regarding safety and security.  The Assistant Superintendent / Human Resources may be required to work in an adult correctional facility and may be required to stand and walk for prolonged periods of time.  This position will be required to travel to other MSO facilities, when necessary.

Qualifications:
  • Eight to (8) to ten (10) years of progressive human resources management experience, correctional setting preferred. Bachelor’s degree, preferred;
  • SHRM Senior Certified Professional (SHRM-SCP) or SHRM Certified Professional (SHRM-CP) credential, preferred. 
  • Proven working knowledge of basic principles and practices of public human resources management;
  • Strong listening skills and the ability to solve problems and de-escalate situations in a timely manner;
  • Strong conflict resolution, analytical and diplomacy skills;
  • Ability to build collaborative relationships with internal and external stakeholders;
  • Proven ability to work independently in a fast-paced environment, oriented, able to handle a large volume of work and pay close attention to detail;
  • Sound oral, written, organizational, time management and decision-making skills with the ability to maintain comprehensive and cohesive records;
  • Ability to apply sound judgment beyond a specific set of instructions and apply knowledge to different factual situations;
  • Possess the capacity to work in a high stress environment on a regular or continuous basis and complete tasks that are time sensitive all while maintaining a positive attitude;
  • Working knowledge of payroll and human resource management systems;
  • Proficient in all Microsoft applications.
In compliance with federal law, all persons hired will be required to verify identity and eligibility to work in the United States and to complete the required employment eligibility verification form upon hire.  Must have an active valid driver’s license, the right to legally operate a motor vehicle in Massachusetts and pass a criminal background check, which includes medical, drug (including marijuana) and psychological screenings.

Salary:  Starting salary range is $140,853.57 to $146,544.07 plus additional incentives, bonuses and employment benefits. Interested candidates can review this job posting at www.middlesexsheriff.org and may submit a cover letter and resume via email to HR@sdm.state.ma.us.

Submissions must be received by May 11, 2026 at 5:00p.m.

 

Salary : $140,854 - $146,544

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