Supervisor, Benefit Operations

The Aspen Group•Chicago, IL

About The Position

The Aspen Group (TAG) is a large retail healthcare business support organization that supports over 23,000 healthcare professionals and team members across 48 states in dental care, urgent care, medical aesthetics, and animal health. TAG provides business support services for Aspen Dental, ClearChoice Dental Implant Centers, WellNow Urgent Care, Chapter Aesthetic Studio, and Lovet Pet Health Care. The Supervisor, Benefits Operations will be a hands-on subject matter expert for the day-to-day administration of benefit programs for a large, multi-brand workforce of over 20,000 employees. This role directly oversees a team responsible for data analysis, invoice payments, and post-payroll vendor reporting, ensuring accuracy and timeliness. The position partners with the Benefits Director and collaborates with Payroll, HRIS, Team Member Care, and HR Partners to support end-to-end benefits processes and maintain regulatory compliance.

Requirements

5+ years of experience in benefits administration for large employers.
Working knowledge of self-funded insurance plans and related claims management for large employers.
Bachelor's degree or equivalent work experience.
Functional HR knowledge and understanding of best practices related to employee transactions, events, and lifecycle.
Demonstrated ability to handle multiple parallel tasks concurrently to meet deadlines, balancing conflicting demands.
Ability to balance daily support for escalated issues with driving ongoing process improvements.
Strong attention to detail and commitment to accuracy in a high-volume administrative environment.

Nice To Haves

1-2 years of supervisory or team lead experience preferred.
Strong ownership of and functional understanding of benefit and wellness programs and processes.
Workday experience preferred.

Responsibilities

Oversee the day-to-day administration of benefit programs for a large workforce of over 20,000 employees across multiple brands.
Support the HRIS team in maintaining and testing benefits and annual open enrollment configuration in Workday.
Directly supervise and coordinate the team handling day-to-day benefits administration, including data analysis, invoice payments, and post-payroll reporting to vendors.
Coordinate with Payroll, HRIS, Team Member Care, and HR Partners to ensure end-to-end benefits processes run smoothly and issues are resolved promptly.
Serve as the first point of escalation for day-to-day vendor issues, invoice discrepancies, and service-level concerns, keeping the Benefits Director informed of trends and unresolved matters.
Provide day-to-day support to brand HR partners and plan providers, resolving routine questions and escalating complex issues as needed.
Identify opportunities for process improvement within the team and help implement best practices in partnership with the Benefits Director.
Assist with monitoring, testing, and documenting compliance activities related to benefits programs, including HIPAA, ERISA, ACA, 1094/1095, COBRA, 401(k) audits, non-discrimination testing, and Form 5500s.
Provide day-to-day guidance, training, and support to team members, ensuring accuracy and timeliness across all benefits administration activities.
Assist with performance goal-setting, performance reviews, and coaching for direct reports, in partnership with the Benefits Director.
Ensure adequate staffing coverage and workload distribution to meet service-level expectations.
Partner with HR and cross-functional leaders to build team capability and ensure consistent, high-quality service delivery.