Benefits And Wellness Supervisor
DEPT OF EMPLOYEE RELATIONS
- Agency: DEPT OF EMPLOYEE RELATIONS
- Location: WI
- Salary: $83K - $108K
- Type: full-time
- Work arrangement: onsite
- Posted: 2026-06-25
Job Description
Introduction
Recognized by the Wellness Council of America (WELCOA) as a
national Well Workplace, the City of Milwaukee is committed to protecting and
enhancing the health and well‑being of our most valuable asset, our employees.
The City of Milwaukee is proud to employ a diverse workforce
dedicated to delivering exceptional service to its residents. If you are
passionate about being part of an inclusive team of public servants, please
consider the following opportunity.
Purpose
The Benefits and Wellness Supervisor oversees daily benefits
operations, manages benefits-related systems and processes within the Human
Resources Information System (HRIS), supervises benefits staff and coordinates
employee outreach, engagement, and education initiatives.
The City of Milwaukee's benefits programs include health and
dental insurance, a comprehensive wellness program, on-site clinics, an on-site
nurse liaison, flexible spending and health reimbursement, long-term disability
insurance, life insurance, tuition reimbursement, a commuter value pass, and
other voluntary benefits focused on healthcare and wellness.
Essential Functions
Benefits Administration
Assist the Employee Benefits Director in overseeing employee
benefit programs.
Lead and execute all aspects of the annual open enrollment
process, including strategic employee communications, educational outreach,
enrollment support and comprehensive system testing; ensure a seamless and
successful enrollment experience.
Monitor and maintain benefits eligibility, enrollment, life
event changes and other benefits transactions.
Review benefits processes and recommend improvements to
increase efficiency, accuracy, and employee satisfaction.
Ensure compliance with applicable laws, regulations and
reporting requirements related to employee benefits.
HR and Benefits Systems Management
Serve as the primary administrator for benefits-related
functions within the HRIS and other benefits management systems.
Oversee system configuration, testing, troubleshooting, data
integrity and ongoing process enhancements.
Collaborate with payroll, Information Technology (IT) and
external vendors to resolve system issues and implement upgrades or new
functionality.
Develop and maintain reports, metrics and dashboards related
to benefits participation, utilization and program performance.
Employee Outreach and Communications
Develop and coordinate benefits communication strategies
that increase employee awareness and understanding of available programs and
resources.
Create and distribute benefits and wellness materials
through various communication channels, including newsletters, intranet
content, presentations, and informational campaigns.
Conduct benefits orientations, informational meetings, and
educational workshops for employees and retirees.
Promote employee engagement and participation in benefits
and wellness initiatives.
Provide oversight to and administer the New Employee
Orientation (NEO) presentation related to employee benefits, both in-person and
virtual.
Wellness Program Coordination
Assist in the planning, implementation, and evaluation of
employee wellness programs and initiatives.
Coordinate wellness events, health education programs,
screenings, challenges, and awareness campaigns.
Collaborate with vendors, healthcare partners, and internal
stakeholders to enhance wellness offerings and employee participation.
Track program outcomes and participation metrics to assess
effectiveness and identify opportunities for improvement.
Supervision and Customer Service
Supervise and provide leadership to a team responsible for
responding to benefits-related inquiries from employees and retirees across the
organization.
Establish service standards, workflows, and performance
expectations to ensure timely and accurate customer support.
Provide training, coaching, and professional development
opportunities for staff.
Serve as an escalation point for complex benefits questions,
concerns, and employee situations.
Vendor and Program Administration
Coordinate with benefits carriers, brokers, consultants,
wellness vendors, and third-party administrators to ensure effective program
delivery.
Assist in contract administration, vendor performance
monitoring, and issue resolution.
Support benefits audits, data requests, and program
evaluations.
We welcome qualified individuals with disabilities who are
interested in employment and will make reasonable accommodations during the
hiring process in accordance with the Americans with Disabilities Act (ADA) of
1990, as amended by the Americans with Disabilities Act Amendments Act (ADAAA)
of 2008.
Conditions of Employment
The Benefits and Wellness Supervisor must be willing and
able to work occasional evening and weekend hours to meet departmental needs.
Minimum Requirements
Bachelor's degree in human resources management, public
administration, or a closely related field from an accredited college or
university.
Three years of progressively responsible experience in
benefit program administration and plan design, including comprehensive
wellness program development.
Ability to travel independently around the City of Milwaukee
by public transportation, walking, biking, or driving.
Equivalent combination of education and experience may be
considered.
NOTICE: Please do not attach your academic transcripts
to your employment application. The hiring department will verify candidates'
education as part of the background screening process prior to extending any
job offers.
Desirable Qualifications
Experience with a large employer or in the public sector.
International Foundation of Employee Benefit Plans Certified
Employee Benefits Specialist (CEBS) designation.
WELCOA Certified or similar certification.
Experience in customer-facing enterprise communications.
Knowledge, Skills, Abilities & Other Characteristics
Technical
Knowledge of various employee benefit programs, plan design
variations, and administration.
Knowledge of survey methodology and questionnaire
development, as well as strategies to encourage and ensure high response rates.
Knowledge of statistical analysis methods to interpret and
measure data trends from utilization reports, surveys, and report findings.
Ability to track, measure, and evaluate various benefit and
wellness program components.
Proficiency using intermediate to advanced features of
Microsoft Word, Excel, and PowerPoint, Adobe Acrobat and/or InDesign, and other
creative applications to develop program materials, marketing pieces,
presentations, and reports.
Knowledge of HRIS systems, benefits administration
technology, and reporting tools.
Enterprise communications knowledge and skills to share
information and engage with internal and external audiences.
Ability to implement benefit and wellness communication and
marketing campaigns incorporating social media strategies and interactive
learning components such as Brainshark and video clips.
Knowledge of and experience using human resources and
benefits administration systems.
Knowledge of applicable federal and state regulations,
including Employee Retirement Income Security Act (ERISA), ACA, Family Medical
Leave Act (FMLA), and Consolidated Omnibus Budget Reconciliation Act (COBRA).
Knowledge of Health Insurance Portability and Accountability
Act (HIPAA) compliance and ability to ensure that appropriate policies,
procedures, and training programs are in place.
Knowledge of webinar creation, scheduling, promotion, and
hosting.
Ability to read and interpret job-related materials such as
reports, policies, and procedures.
Ability to assist with policy and benefit plan formulation
and implementation.
Knowledge of mathematics to assist with financial and budget
projections.
Knowledge of employer healthcare and wellness trends
Supervisory
Knowledge of supervisory principles and best practices.
Ability to effectively lead a team of professional benefits
staff.
Ability to assign duties, set clear performance standards,
provide coaching and training, monitor work in progress, evaluate performance,
and make hiring recommendations.
Ability to foster an environment of inclusion wherein all
employees are treated respectfully, are valued for their strengths, and feel
that they can safely express themselves.
Communication and Interpersonal
Verbal communication skills to speak clearly and concisely
to internal and external customers.
Presentation skills to deliver benefit and wellness program information,
reports, and data to various audiences.
Written communication skills to develop clear and engaging
marketing and communication materials, informational program materials,
reports, presentation materials, and correspondence.
Ability to work effectively with team members,
representatives of City of Milwaukee departments, vendor partners, and City
officials.
Ability to work cooperatively and fairly with people whose
backgrounds may differ from one's own.
Ability to communicate complex benefit information clearly
and effectively to a wide variety of professionals.
Critical Thinking and Professionalism
Analytical and problem-solving skills.
Decision-making skills and sound judgment.
Ability to work well independently.
Ability to manage multiple priorities and work within tight
time constraints to meet deadlines.
Attention to detail.
Ability to remain calm and professional while working within
a fast-paced environment.
Honesty, integrity, and the ability to handle confidential
employee information with discretion in compliance with HIPAA standards.
Commitment to continuous learning relative to
benefits and employee wellness.
Current Salary
The current salary range (Pay Range 1HX) is $82,677-$108,380 annually,
and the resident incentive salary range for City of Milwaukee residents
is $85,984-$112,715 annually. Appointment above the
minimum is possible based upon level of experience and other qualifications and
is subject to approval.
BENEFITS ~ The City of Milwaukee
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