Senior Retirement Benefits Specialist

About Acrisure

Acrisure is a global Fintech leader that combines the best of humans and high tech to offer multiple financial products and services to millions of businesses and individual clients. We connect clients to solutions that help them protect and grow what matters, including Insurance, Reinsurance, Cyber Services, Mortgage Origination and more.

Acrisure employs over 17,000 entrepreneurial colleagues in 21 countries and have grown from $38 million to $4.3 billion in revenue in just over ten years. Our culture is defined by our entrepreneurial spirit and all that comes with it: innovation, client centricity and an indomitable will to win.

Job Summary

The Senior Benefits Specialist serves as a subject matter expert on employee benefits and plays a key role in complex issue resolution, plan audits, system configuration testing, and process improvements. This role partners cross-functionally with Payroll, HRIS, Legal, and vendors to support escalated issues, compliance efforts, and strategic planning initiatives such as open enrollment.

Responsibilities

• Resolve escalated employee benefit isses with a high level of accuracy and professionalism.
• Lead audits of internal and vendor benefit data to ensure compliance and integrity.
• Contribute to the planning and execution of annual open enrollment, including system testing, communications, and timeline management.
• Serve as a Workday subject matter expert for benefits, leading testing and validation of new configurations or processes.
• Partners with HRIS, Payroll, and vendors to troubleshoot issues and improve workflows.
• Analyze benefit trends, utilization data, and compliance metrics to support strategic improvements.
• Provide guidance to Benefits Specialists and help develop training materials and job aids.
• Maintain expert-level knowledge of ERISA, ACA, HIPAA, COBRA, and Section 125 rules.
• Education & Experience
• 3–5 years of experience in employee benefits administration.
• Bachelor’s degree preferred; equivalent experience considered.
• Strong understanding of ERISA, ACA, COBRA, HIPAA, and IRS Section 125 regulations.
• Advanced knowledge of HRIS systems (Workday preferred), including configuration testing and reporting.
• Proven critical thinking, analytical, and problem-solving skills.
• Experience supporting or managing annual open enrollment cycles.
• Ability to communicate effectively with employees, leadership, and external partners.
• Candidates should be comfortable with an on-site presence to support collaboration, team leadership, and cross-functional partnership.

Why Join Us:

At Acrisure, we’re building more than a business, we’re building a community where people can grow, thrive, and make an impact. Our benefits are designed to support every dimension of your life, from your health and finances to your family and future.

Making a lasting impact on the communities it serves, Acrisure has pledged more than $22 million through its partnerships with Corewell Health Helen DeVos Children's Hospital in Grand Rapids, Michigan, UPMC Children's Hospital in Pittsburgh, Pennsylvania and Blythedale Children's Hospital in Valhalla, New York.

Employee Benefits

We also offer our employees a comprehensive suite of benefits and perks, including:

• Physical Wellness: Comprehensive medical insurance, dental insurance, and vision insurance; life and disability insurance; fertility benefits; wellness resources; and paid sick time.
• Mental Wellness: Generous paid time off and holidays; Employee Assistance Program (EAP); and a complimentary Calm app subscription.
• Financial Wellness: Immediate vesting in a 401(k) plan; Health Savings Account (HSA) and Flexible Spending Account (FSA) options; commuter benefits; and employee discount programs.
• Family Care: Paid maternity leave and paid paternity leave (including for adoptive parents); legal plan options; and pet insurance coverage.
• … and so much more!
• This list is not exhaustive of all available benefits. Eligibility and waiting periods may apply to certain offerings. Benefits may vary based on subsidiary entity and geographic location.

Final candidates will be required to complete post-offer verification processes related to the role and in accordance with applicable laws.

California Residents: Learn more about our privacy practices for applicants by visiting the Acrisure California Applicant Privacy Policy .

Recruitment Fraud: Please visit here to learn more about our Recruitment Fraud Notice .

Welcome, your new opportunity awaits you.