Assistant Director of Benefits and Wellness - Fort Myers, FL
Job Title: Assistant Director of Benefits and Wellness
School District (Location of Position): The School District of Lee County
City/State (of Position): Fort Myers, FL
Where to Apply: https://apply.leeschools.net/
Position Open Until: 11/6/2026
Job Description: The Assistant Director of Benefits and Wellness ensures compliance with benefits regulations, manages vendor relationships, and develops strategies to enhance employee well-being. The position plays a key role in providing high-quality benefits administration while promoting a culture of health and wellness for all district employees.
Minimum Qualifications: Education: Bachelor’s degree in Business Administration, Risk Management, Human Resources, Public Administration, or a related field. Professional Experience: Minimum of 6 years of progressively responsible experience in employee benefits administration, workers’ compensation, property/casualty insurance, or wellness initiatives. Large-Scale Enterprise Experience: Proven experience administering benefits and risk/insurance programs within a large organization serving 10,000+ employees.
People Leadership: Minimum of 3–5 years of direct supervisory experience managing and leading a team of 10 or more HR, benefits, or risk management professionals.
Labor Relations & Unionized Environment: Demonstrated expertise working within a unionized setting (e.g., school-based or public sector), including interpreting collective bargaining agreements (CBAs), working with contract language, and collaborating with labor representatives on benefit structures.
Performance Measurement & Analytics: Proven track record of setting strategic goals, tracking KPIs, monitoring project success, and providing quantitative evidence of goal achievement (e.g., ROI, cost containment, program utilization). Relevant work experience or education may be substituted to satisfy minimum qualifications.
Essential Job Functions: Administer, direct, and review employee benefit programs, including the District’s self-insured health plan to ensure fiscal stability. Plan and direct selection, implementation, and administration of voluntary employee benefits. Design, evaluate, and modify benefit policies to ensure that programs are current, competitive, and in compliance with legal requirements. Manage the design and development of tools to assist employees in benefits selection. Fulfill reporting requirements of relevant government rules and regulations. Direct preparation and distribution of written and verbal information to inform employees of benefits and workers compensation policies. Chair and coordinate all activities of the District’s Insurance Task Force. Plan, direct, supervise, and coordinate work activities of subordinates and staff. Oversees the administration of retirement, Americans with Disability (ADA), and leave of absence management. Serves as the primary contact for vendors.
Reports to: Senior Director, Employee Relations or Designated Administrator
Starting Pay: $91,759.20Compensation may increase based upon relevant education and experience.
Days per year: 255
Benefits: Employee Health Insurance Employee Life Insurance Retirement Plan Employee Assistance Plan FSA and HSA Programs Employee Wellness Program Sick Time and Paid Time Off
Your Perks: 3 levels of employee insurance plans
Paid Parental Leave: Up to 4 weeks, 20 consecutive work days Access to discounted childcare options for employees Retirement programs Employee benefits & wellness programs including monetary incentives Free access to state-of-the art gym (located at district office), Free professional development
About the School District of Lee County: The School District of Lee County is the eighth-largest district in Florida and the 27th-largest school district in the United States*. We proudly educate over 101,000 students in grades K-12. Schools in Lee County play a key role in community life. With 12,000+ full- and part-time employees, the School District is one of the county's largest employers, and with the District's construction program, building new schools, and renovating and expanding existing facilities, the District has been the area's largest developer.
*Source: National Center for Education Statistics
To Apply: 1- Visit https://apply.leeschools.net/
2- In the search toolbar, enter 20262538
3- Click the arrow to the right-hand side of the job details
4- Click "Apply for Job" in the upper right-hand corner