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TAG - The Aspen Group · 1 day ago

Director, Benefits

Chicago, IL

Full-time

Onsite

Director/Executive

$175K/yr - $175K/yr

8+ years exp

TAG - The Aspen Group is one of the largest and most trusted retail healthcare business support organizations in the U.S., supporting over 20,000 healthcare professionals. The Director of Benefits is responsible for the design, strategy, and evolution of enterprise benefit programs, ensuring they align with TAG's business objectives and providing leadership for Benefits Administration and Leave of Absence functions.

CosmeticsDentalHealth CareWellness

Hiring Manager

Kelly (Dillon) Campagna

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

Qualification

Benefits strategyBenefits designCompliance knowledgeHRIS experienceClaims analyticsVendor selectionFinancial stewardshipLeadershipCommunicationTeam collaborationProblem-solving

Required

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

Preferred

Advanced degree or professional certifications (e.g., CEBS) a plus

Experience transitioning from fully insured to self-funded plans strongly preferred

Workday experience strongly preferred

Benefits

Paid time off

Health

Dental

Vision

401(k) savings plan with match

Company

TAG - The Aspen Group

When we launched Aspen Dental, we set out to break down the barriers that made it hard for patients to keep up with their dental health — affordability, transparency, and access.

Founded in 1998

Chicago, Illinois, USA

10001+ employees