Sr Benefits Specialist
CDW
- Location
- Virtual - Illinois
- Work model
- On-Site
- Level
- Senior
- H-1B history
- 19 approvals (FY2023)
- Posted
- Aug 18, 2026
About this role
The Senior Benefits Specialist is a key contributor to CDW's Total Rewards and Benefits strategy, responsible for supporting the design, administration, compliance, communication, and continuous improvement of health, welfare, retirement, and wellbeing programs. This role partners closely with benefit brokers, insurance carriers, vendors, payroll, HR, legal, and other cross-functional stakeholders to ensure benefit programs are competitive, compliant, cost-effective, and aligned with business objectives. The Senior Benefits Specialist serves as a subject matter expert for benefit programs, helping drive strategic initiatives, support vendor and carrier relationships, analyze program effectiveness, resolve complex employee issues, and assist with the implementation of new programs and enhancements. Success in this fast-paced environment requires strong analytical capabilities, exceptional organizational skills, proactive problem-solving, cross-functional collaboration, and a commitment to delivering an exceptional coworker experience.
What you will do
Design health and welfare, retirement, and wellness programs, ensuring programs align with organizational objectives and regulatory requirements. Partner with benefit brokers, consultants, carriers, and third-party administrators throughout plan renewals, annual enrollment activities, and ongoing program administration. Support the implementation of new benefit programs, plan enhancements, system integrations, and process improvements. Analyze plan utilization, participation trends, and program effectiveness to identify opportunities for enhancement and cost optimization. Assist in developing and maintaining benefit policies, procedures, and governance frameworks. Build and maintain effective working relationships with benefit vendors, insurance carriers, brokers, and consultants. Participate in vendor evaluations, Requests for Proposal (RFPs), contract reviews, and implementation activities. Monitor vendor performance, service levels, and operational effectiveness. Coordinate participant issue resolution with carriers and vendors and ensure timely follow-up on escalated matters. Support ongoing benefit program audits and vendor performance reviews. Serve as an escalation point for complex benefit inquiries, claims issues, enrollment concerns, and vendor-related matters. Partner with internal and external stakeholders to facilitate timely resolution of coworker benefit concerns. Support benefit communications and educational initiatives that enhance employee understanding and engagement. Identify opportunities to improve service delivery and the overall coworker experience. Ensure benefit programs comply with applicable federal, state, and local regulations, including ERISA, COBRA, HIPAA, ACA, and other relevant requirements. Support preparation and maintenance of required plan documentation, including Summary Plan Descriptions (SPDs), plan notices, participant disclosures, and regulatory filings. Coordinate compliance-related activities, annual testing, and reporting requirements. Assist with internal and external audits and provide supporting documentation as requested. Partner with Legal, Payroll, HRIS, and external vendors to ensure compliance obligations are met. Collect, analyze, and interpret benefits data to support decision-making and strategic planning. Monitor marketplace trends, emerging benefit practices, and legislative developments to provide recommendations for program enhancements. Prepare reports, presentations, and business cases for leadership regarding benefit program performance and opportunities. Support annual budgeting, forecasting, enrollment reporting, and benefits analytics. What we expect of you Bachelor’s degree in business, mathematics, finance, health administration, human resources, or related field and 5+ years of employer benefits experience in plan design and financial analysis OR 9+ years of employer benefits experience in plan