Sr Benefits Specialist

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. 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. Assist in developing and maintaining benefit policies, procedures, and governance frameworks. Participate in vendor evaluations, Requests for Proposal (RFPs), contract reviews, and implementation activities. Monitor vendor performance, service levels, and operational effectiveness. 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. Support benefit communications and educational initiatives that enhance employee understanding and engagement. 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. 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. Prepare reports, presentations, and business cases for leadership regarding benefit program performance and opportunities. 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 design and financial analysis Strong knowledge and understanding of health plan benefit plan design, plan service/administration procedures, health plan underwriting/actuarial principles/funding, and compliance requirements such as ERISA, ACA, COBRA, HIPAA, IRS Section 125, and MHPAEA. Ability to gather and analyze data, reason logically and creatively, draw conclusions, and make appropriate recommendations. Ability to be flexible and adapt to change. Strong creative problem-solving skills and resourcefulness. Proficient in Microsoft Office including Copilot. Workday experience is a plus. Annual bonus target of 5% subject to terms and conditions of plan Additionally, CDW is committed to fostering an equitable, transparent, and respectful hiring process for all applicants. During our application process, our goal is to understand your experience, strengths, skills, and qualifications. We welcome thoughtful use of AI to expand your perspective and elevate how you share your story, while ensuring your application remains rooted in your own background, judgment, and voice. CDW is a Fortune 500 technology solutions provider that helps businesses, government, education, and healthcare organizations achieve what’s possible through technology. At CDW we act as one—building trust, speaking candidly, and working together to achieve more. We play to win—focusing on what matters most and delivering for our customers. That’s why we think of ourselves as coworkers, not just employees—working together to solve complex challenges and deliver real impact for our customers and communities. As a full‑stack, full‑lifecycle technology partner, CDW brings deep expertise, strong relationships, and broad industry knowledge to help turn ideas into outcomes. When you join CDW, you become part of a collaborative environment where your work matters, your growth is supported, and your contributions help shape what’s next. Together, we deliver the full promise of what technology can do. All qualified applicants will receive consideration for employment without regards to race, color, religion, sex, sexual orientation, gender identity, national origin, disability status, protected veteran status or any other basis prohibited by state and local law.