Director, Benefits

AA IL Chicago Corporate Office (Bryn Mawr)

We put our team members first. You’ll receive a great salary and benefits, and experience the support and opportunity you deserve. You’re empowered to make decisions. You control your future.

Job Description

The Director, Benefits is responsible for the strategic planning, development, implementation, and administration of the organization’s benefits programs, including health and wellness, retirement, leave policies, workers compensation, and other employee perks in both USA and Canada. This role ensures compliance with all regulatory requirements, aligns benefits offerings with organizational goals, and enhances employee satisfaction and retention. Lead a team of three direct reports and 2 indirect reports.

Job Responsibilities

• Strategic Planning & Program Management
• Develop and lead the company’s benefits strategy to attract and retain top talent.
• Design, implement, and evaluate health, wellness, and retirement programs to ensure competitiveness and cost-effectiveness.
• Conduct benchmarking and industry research to continuously improve benefit offerings.
• Partner with senior leadership and HR teams to align benefits programs with overall business objectives.
• Workers Compensation report to this role.
• Benefits Administration & Compliance
• Oversee administration of all employee benefits programs, including health insurance, dental, vision, disability, FSA/HSA, life insurance, and 401(k) plans.
• Ensure compliance with federal, state, and local regulations (e.g., ACA, ERISA, HIPAA, COBRA, FMLA, and ADA).
• Manage vendor relationships, negotiate contracts, and optimize service delivery for benefits providers.
• Monitor and analyze benefits utilization data to identify trends and recommend improvements.
• Employee Engagement & Communication
• Manage the Open Enrollment Process including all screen flows, EOI and Confirmation Statements.
• Develop and deliver employee education programs on benefits, retirement planning, and wellness initiatives.
• Serve as the main point of contact for employee inquiries regarding benefits policies and programs.
• Enhance employee experience by ensuring benefits offerings are clearly communicated and accessible.
• Financial Management & Reporting
• Oversee benefits budget, including cost analysis, forecasting, and financial reporting.
• Work with Finance and HR teams to evaluate the financial impact of benefits changes and cost‑containment strategies.
• Prepare reports and presentations for leadership on benefits trends, participation, and cost management.
• Manage all billings, invoicing and reconciliations.
• Ensure all contracts are loaded into Workday correctly, employees are billed appropriately per paycheck, and vendor bills are paid based on the contract.

Education And/or Experience Requirements

• Bachelor's degree in Human Resources, Business Administration, or a related field required. Master's degree preferred.
• A minimum of 8 years of progressive experience in benefits management, with at least 4 years in a leadership role.
• CEBS, PHR/SPHR, SHRM-CP/SCP, or related certifications preferred.

Required Knowledge, Skills, & Abilities

• Strong leadership and team management skills.
• Proficiency in HRIS systems (preferably Workday HCM), benefits administration software, and data analytics tools.
• Experience with ADP payroll.
• Experience with Google Suite tools.
• Deep knowledge of benefits laws and regulations.
• Excellent analytical, negotiation, and financial management skills.
• Strong communication and employee engagement capabilities.
• Ability to manage multiple projects and meet deadlines in a fast‑paced environment.

Other Requirements (i.e., Physical Requirements, Travel, Etc.)

• Ability to work on a personal computer or laptop for extended periods of time.
• Hybrid (4 days a week mandatory) or full on-site work environment.

AI Disclosure Statement

At The Boyd Group and all affiliated companies, we do not use artificial intelligence (AI) or automated tools to screen, assess, or select applicants for employment. All hiring decisions are made by real people who review each application individually.

Compensation Details

$180,000 - $210,000 / Year

Compensation is commensurate with skill, education and experience. This position may also be eligible for bonus opportunities tied to individual or business initiatives.