Director, Benefits

The Aspen Group•Chicago, IL

About The Position

The Aspen Group (TAG) is one of the largest and most trusted retail healthcare business support organizations in the U.S., supporting more than 20,000 healthcare professionals and team members across 1,400+ health and wellness offices in 48 states. TAG operates across Dental Care, Urgent Care, Medical Aesthetics, and Animal Health, and provides centralized business support services to five consumer-facing brands: Aspen Dental, ClearChoice Dental Implant Centers, WellNow Urgent Care, Chapter Aesthetic Studio, and Lovet. Working in partnership with independent practice owners and clinicians, TAG is united by a single purpose: to prove that healthcare can be better and smarter for everyone. Backed by top-tier private equity firms, TAG operates through a center-of-excellence model that enables scale, consistency, and continuous improvement. What You Will Be Doing The Director of Benefits is accountable for the design, strategy, and evolution of enterprise benefit programs , ensuring they are competitive, scalable, and aligned with TAG’s business and talent objectives. This role sets the long-term benefits roadmap and governs execution through strong operational leadership of Benefits Administration and Leave of Absence functions.

Requirements

You are a strategic benefits leader who excels at program design, financial stewardship, and executive advisory , with the ability to govern operations through strong teams and processes.
8–12+ years of progressive experience in benefits strategy, design, or total rewards within large, complex organizations.
Demonstrated experience leading benefits design initiatives, including plan modeling, funding strategy decisions, and vendor selection.
Experience managing Benefits Administration and Leave of Absence teams , with a governance-oriented leadership approach.
Deep expertise in self-funded health plans, claims analytics, and cost-containment strategies; experience transitioning from fully insured to self-funded plans strongly preferred.
Strong command of benefits-related compliance requirements and risk management for large employers.
Proven ability to partner with Finance and HR leadership on budgeting, forecasting, and long-range planning.
Experience working with HRIS platforms to translate benefits design into scalable system configuration; Workday experience strongly preferred .
Bachelor’s degree required; advanced degree or professional certifications (e.g., CEBS) a plus.
Comfortable influencing senior leaders and operating in a private-equity-backed, high-growth environment.

Nice To Haves

advanced degree or professional certifications (e.g., CEBS)
experience transitioning from fully insured to self-funded plans strongly preferred.
Workday experience strongly preferred

Responsibilities

Own the enterprise benefits strategy and design philosophy across health and welfare, retirement, wellbeing, and leave programs, balancing competitiveness, cost efficiency, and team member experience.
Partner with Total Rewards leadership, Finance, and external consultants to design benefit programs that support attraction, retention, engagement, and workforce wellbeing across a 20,000+ employee population.
Lead multi-year benefits planning, including vendor selection, plan design changes, funding strategies, and cost-containment initiatives.
Evaluate benefits utilization, claims data, market benchmarking, and employee feedback to inform design decisions and executive recommendations.
Serve as the senior subject matter expert on benefits design, advising executive leadership on trade-offs, risk, and investment decisions.
Guide benefits-related M&A integration strategy, ensuring program design alignment and scalable transition approaches.
Provide leadership and governance for Benefits Administration and Leave of Absence teams , ensuring operational excellence, compliance, and a high-quality service experience.
Set clear expectations, performance standards, and escalation models for benefits and LOA administration while avoiding unnecessary involvement in daily transactional work.
Partner with HRIS to oversee benefits configuration, open enrollment, and system governance within Workday, ensuring design intent is accurately executed.
Oversee non-Workday benefits processes, including paid parental leave programs, vendor integrations, student loan benefits, and post-payroll vendor reporting.
Ensure all benefits and leave programs are administered in compliance with applicable regulations, including HIPAA, ERISA, ACA, COBRA, and related reporting and audit requirements.
Act as an escalation point for complex or high-risk benefits and leave cases as needed.
Partner cross-functionally with Payroll, HRIS, Legal, Finance, Team Member Care, and Brand HR leaders to ensure benefits design decisions are operationally viable and consistently executed.
Establish enterprise standards for benefits communications, governance, and change management, ensuring clarity and alignment across brands.
Oversee benefits-related intranet content and communication strategy in support of design changes and annual enrollment activities.