Senior Benefits & Wellness Manager

JEFF WYLER AUTOMOTIVE FAMILY•Milford, OH

23h•Onsite

About The Position

The Jeff Wyler Automotive Family Senior Benefits & Wellness Manager is responsible for the strategic oversight, administration, compliance, and continuous improvement of the company’s employee benefits and wellness programs across a multi-state organization. This role serves as a key business partner in managing self-insured healthcare programs, vendor relationships, employee wellbeing initiatives, and benefits related compliance obligations while also acting as a trusted resource for employees navigating complex or sensitive personal situations. The position partners closely with executive leadership, brokers, carriers, vendors, payroll, finance, and HR leadership to develop benefits strategies that balance employee experience, compliance, financial stewardship, and organizational objectives.

Requirements

Bachelor’s degree in human resources, Business Administration, Healthcare Administration, or related field preferred.
7+ years of progressive Benefits Administration experience with exposure to self-insured healthcare plans strongly preferred.
Strong understanding of employee benefits compliance including FMLA, ADA, ACA, COBRA, HIPAA, and ERISA.
Experience working with brokers, carriers, stop loss providers, and third-party administrators.
Strong analytical and financial acumen with the ability to interpret claims data, utilization trends, and renewal projections.
Exceptional interpersonal, communication, and employee relations skills.
Demonstrated ability to handle confidential and emotionally sensitive situations with professionalism, empathy, discretion, and sound judgment.
Experience supporting multi location or multi state operations preferred.
Proficiency with HRIS systems and Microsoft Excel required.
Experience with Paycom preferred.

Nice To Haves

Strategic thinker with strong operational execution skills.
High level of emotional intelligence and professionalism.
Strong attention to detail and compliance orientation.
Ability to build trust and credibility across all levels of the organization.
Calm, approachable, and solutions focused under pressure.
Strong desire to continue learning and developing.

Responsibilities

Lead the administration and strategic oversight of all employee benefit programs including medical, dental, vision, life, disability, voluntary benefits, wellness initiatives, COBRA, leave related programs, and retirement benefits.
Partners with brokers, carriers, consultants, and vendors to evaluate plan performance, claims trends, renewal strategies, cost containment opportunities, and employee experience improvements.
Support the ongoing management and financial oversight of the company’s self-insured healthcare programs including review of high-cost claims, stop loss coverage, healthcare utilization trends, funding recommendations, and overall plan performance.
Analyze benefits data, utilization reports, renewal projections, and market trends to support leadership decision making and long-term benefits planning.
Oversee compliance and administration related to FMLA, ADA coordination, ACA, COBRA, HIPAA, ERISA, workers’ compensation claims administration, Section 125 plans, SPD administration, open enrollment processes, and 1094/1095 reporting requirements.
Oversee administration of the company’s 401(k) retirement plan, including vendor management, employee education, compliance activities, audits, and ongoing plan support.
Serve as a primary point of contact for employees and family members experiencing sensitive or complex situations including medical leaves, disability concerns, loss of life events, benefit escalations, and other personal hardships requiring empathy, discretion, confidentiality, and support.
Coordinate leave related processes and partner with internal and external stakeholders to support employees through medical leaves, accommodations, and return to work transitions.
Lead annual Open Enrollment planning, employee education, communication strategies, and benefits related training initiatives.
Develop and support employee wellness initiatives focused on employee wellbeing, engagement, preventive care, and overall benefits utilization.
Partner with payroll, HR, and operational leadership to ensure accurate benefit deductions, eligibility management, leave coordination, and Paycom integrations.
Monitor regulatory changes and recommend updates to policies, procedures, and benefit programs to maintain compliance and operational effectiveness.
Assist with benefits audits, vendor performance reviews, and ongoing process improvement initiatives.