City of Boston

Assistant Director of Health Benefits & Insurance

Req ID
ASD Human Resources
Regular Full-Time
ASD-Health Ben & Ins
Salary Min
Salary Max
Posting End Date
Contact Email


The Assistant Director of Health Benefits & Insurance plays a crucial supporting role within the Health Benefits & Insurance department of the City of Boston. This position assists the Director in the oversight and management of administering the health, life, and, ancillary benefits for approximately 50,000 City of Boston employees and retirees. In addition to taking a lead role in the development and implementation of wellness initiatives, the Assistant Director will contribute to the strategic planning, administration, and communication of benefits, ensuring they align with the city's objectives and meet the diverse needs of our workforce.


Benefit Plan Administration and Operational Support:

  • Oversees the day-to-day operations of the health benefits and insurance department, including leading a team of 2 direct reports who are responsible for leading the active employee operations team and the retiree benefit teams within the Health Benefits office.
  • Collaborate with the Director to develop and implement departmental policies, procedures, and guidelines.
  • Ensure accurate and timely processing of benefit enrollments, changes, and terminations.
  • Provide guidance and support to employees and retirees regarding benefit plan options, coverage, and inquiries.
  • Assist in the development and implementation of employee education programs and materials.
  • Support the communication efforts related to open enrollment, benefit plan changes, and other relevant updates.


Employee Wellness

  • Partner with the Wellness Committee to develop and implement a wide range of wellness programs, including fitness, nutrition, mental health, and lifestyle initiatives, tailored to the diverse needs of our workforce.
  • Collaborate with the Employee Experience team to create a wellness calendar of events and communications schedule, as well as oversee the creation and distribution of wellness related employee education materials utilizing a variety of communication channels such as but not limited to, print materials, digital materials, email blasts, newsletters, etc.
  • Analyze program effectiveness and employee health data to continuously improve and adapt wellness initiatives.
  • Work in cohesion with the Health Benefit Finance Manager to oversee the budget for wellness programs and ensure cost-effective solutions.


Vendor Relations:

  • Assist in monitoring vendor performance, resolving escalated issues, and ensuring service delivery standards are met.
  • Participate in the procurement process for various Requests for Proposal for the Health Benefits Office, including assisting with the creation of RFP documents and vendor assessment criteria, as well as with the vendor rating and decision process.


Project Management:

  • Participate in the implementation of new benefits programs and initiatives related to the Health Benefits & Insurance Office.
  • Collaborate with various departments to ensure cohesive project execution.


Strategic Support:

  • Under the direction of the Health Benefits Director, assist in the development and implementation of the city’s health benefits strategy, ensuring alignment with organizational goals and objectives.



  • Performs related work as required.

Minimum Entrance Qualifications:

  • Bachelor’s degree preferred with at least 4 years full-time, or equivalent to 2 years of full-time, program management experience or 3-4 years related experience.
  • At least 2 years of management experience leading direct reports required
  • Sound knowledge of health benefits and insurance industry regulations and best practices, benefit plan design, administration, and compliance.
  • Knowledge of health promotion, fitness, and wellness trends.
  • Strong leadership, and project management skills.
  • Excellent oral and written communications, organizational skills and presentation skills.
  • Proficiency with Microsoft applications, and Google Suite.
  • Strong analytical and problem-solving abilities, with attention to detail.
  • Must be able to maintain confidentiality and discretion as required.


Boston Residency Required.



Union/Salary/Grade: Non-Union/MM2-10

Hours per week: 35



Sorry the Share function is not working properly at this moment. Please refresh the page and try again later.
Share on your newsfeed