Supervisor, Benefit Operations

The Aspen Group; Chicago, Northern (IL, KY); Hybrid; USD 78,000 - 88,000; Full time

Benefits offered by this job

Paid time off

Health insurance

Dental insurance

Vision insurance

401(k) with match

Job summary

The Aspen Group is seeking a hands-on Supervisor, Benefits Operations to oversee day-to-day administration of our benefit programs for a multi-brand workforce of over 20,000 employees. You will lead a team, ensure accuracy, and partner with Payroll, HRIS, and Benefits Directors to deliver end-to-end benefits processes.

Ideal candidates have 5+ years in benefits administration, 1-2 years of supervision, and Workday experience.

Qualifications

• 5+ years of experience in benefits administration for large employers.
• 1-2 years of supervisory or team lead experience preferred.
• Bachelor's degree or equivalent work experience.
• Workday experience preferred.
• Strong attention to detail in a high-volume administrative environment.
• Knowledge of HIPAA, ERISA, ACA, 1094/1095, COBRA, 401(k) audits, and Form 5500s.

Responsibilities

• Oversee day-to-day benefit program administration for a large workforce across multiple brands.
• Support the HRIS integration and enrollment configuration in Workday.
• Directly supervise and coordinate the benefits administration team.
• Coordinate with Payroll, HRIS, Team Member Care, and HR Partners to ensure end-to-end processes.
• Serve as the first point of escalation for vendor issues, invoice discrepancies, and service-level concerns.
• Provide day-to-day support to brand HR partners and plan providers; escalate complex issues as needed.
• Identify opportunities for process improvements and implement best practices with the Benefits Director.
• Assist with monitoring and documenting compliance activities related to benefits programs (HIPAA, ERISA, ACA, COBRA, 1094/1095, etc.).

Skills

Benefits administration

Team leadership

Data analysis

Vendor coordination

Detail-oriented

Education

Bachelor's degree or equivalent

Tools

Workday

HRIS

Job description

## Supervisor, Benefit OperationsApplylocations: Chicago, Illinoistime type: Full timeposted on: Posted 2 Days Agojob requisition id: R2026-009977The Aspen Group (TAG) is one of the largest and most trusted retail healthcare business support organizations in the U.S. and has supported over 23,000 healthcare professionals and team members at more than 1,300 health and wellness offices across 48 states in four distinct categories: dental care, urgent care, medical aesthetics, and animal health. Working in partnership with independent practice owners and clinicians, the team is united by a single purpose: to prove that healthcare can be better and smarter for everyone. TAG provides a comprehensive suite of centralized business support services that power the impact of five consumer-facing businesses: Aspen Dental, ClearChoice Dental Implant Centers, WellNow Urgent Care, Chapter Aesthetic Studio, and Lovet Pet Health Care. Each brand has access to a deep community of experts, tools and resources to grow their practices, and an unwavering commitment to delivering high-quality consumer healthcare experiences at scale.As a reflection of our current needs and planned growth we are very pleased to offer an opportunity to join our dedicated team as Supervisor, Benefits Operations. The Supervisor, Benefits Operations will serve as a hands-on subject matter expert for the day-to-day administration of benefit programs for this large, multi-brand workforce. The Supervisor will directly oversee a team of associates responsible for data analysis , invoice payments, and post-payroll vendor reporting, ensuring accuracy and timeliness across all benefits administration activities. This role partners closely with the Benefits Director and works cross-functionally with Payroll, HRIS, Team Member Care, and HR Partners to support well-defined, end-to-end benefits processes and maintain compliance with applicable benefits regulations.**Essential Responsibilities*****Benefits Operations Program Support**** **Benefit Program Administration:**Oversee the day-to-day administration of benefit programs for a large workforce of over 20,000 employees across multiple brands.* **HRIS Integration:**Support the HRIS team in maintaining and testing benefits and annual open enrollment configuration in Workday.* **Team Leadership:**Directly supervise and coordinate the team handling day-to-day benefits administration, including data analysis, invoice payments, and post-payroll reporting to vendors.* **Cross-Functional Collaboration:**Coordinate with Payroll, HRIS, Team Member Care, and HR Partners to ensure end-to-end benefits processes run smoothly and issues are resolved promptly.* **Vendor Coordination:**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.* **Operational Support:**Provide day-to-day support to brand HR partners and plan providers, resolving routine questions and escalating complex issues as needed.* **Best Practice Implementation:**Identify opportunities for process improvement within the team and help implement best practices in partnership with the Benefits Director.* **Compliance:**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.**Supervision*** Directly supervise a team responsible for benefits processes including data analysis, invoice processing, and post-payroll vendor reporting.* 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.**Requirements & Qualifications*** 5+ years of experience in benefits administration for large employers.* Working knowledge of self-funded insurance plans and related claims management for large employers.* 1-2 years of supervisory or team lead experience preferred.* Strong ownership of and functional understanding of benefit and wellness programs and processes.* Bachelor's degree or equivalent work experience.* Workday experience preferred.* 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.Annual Pay Range: $78-88kA generous benefits package that includes paid time off, health, dental, vision, and 401(k) savings plan with match