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. 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 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.
• Excellent verbal and written communication skills with the ability to effectively interact with all stakeholders, including plan participants and senior leadership.
• History of balancing competing priorities with the ability to adapt to the changing needs of the business while meeting deadlines.
• Ability to gather and analyze data, reason logically and creatively, draw conclusions, and make appropriate recommendations.
• Ability to be flexible and adapt to change.
• History of working independently with little direction.
• Strong creative problem-solving skills and resourcefulness.
• Strong organizational skills.
• Proficient in Microsoft Office including Copilot.
• Workday experience is a plus.

Pay range: $91,000-$126,200 depending on experience and skill set
Annual bonus target of 5% subject to terms and conditions of plan
Benefits overview: https://cdw.benefit-info.com/
Salary ranges may be subject to geographic differentials

CDW is committed to being an AI-fluent organization

We’re looking for people who bring curiosity, a learner’s mindset, and a willingness to engage with ever-evolving technology and tools. We value adopting AI as a partner, openness to experimentation, and a shared interest in learning together on AI. Our goal is to create a culture where AI enhances—not replaces—human creativity and decision-making. You don’t need to be an expert today; what matters is your readiness to explore, adapt, and grow with us as we integrate AI responsibly and effectively into our work.

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. As an AI forward company, we see AI not just as a tool, but as a catalyst for new ways of thinking, creating, and communicating. We encourage candidates to embrace an AI mindset, one that’s curious, adaptive, and ready to explore what’s possible. 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.

About Us

CDW is a Fortune 500 technology solutions provider that helps businesses, government, education, and healthcare organizations achieve what’s possible through technology. What makes CDW different isn’t just what we do—it’s how we do it. 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. And we think forward—staying curious, moving fast, and continuously learning. We believe meaningful work happens when people feel supported, heard, and empowered to contribute. 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. Together, we Make Amazing Happen.

CDW is an equal opportunity employer. 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.