Administrative Assistant; Hybrid

About Dempsey

Since 1968, Dempsey Benefits has been a trusted employee benefits firm, proudly serving hundreds of clients across a broad spectrum of industries. Our dedicated team of advisors and account managers delivers personalized service rooted in hard work, exceptional knowledge, and honesty. We partner closely with employers to develop benefits programs that reflect company culture and deliver value to employees. At Dempsey Benefits, our goal is to be an essential part of your business’s success by providing tailored benefit solutions and unwavering support.

We are seeking a detail-oriented and client-focused Administrative Assistant to support our Employee Benefits Account Management team. This role plays a key part in ensuring smooth renewals, accurate enrollments, and responsive client service for small group accounts. Working closely with Account Managers, this individual will help maintain organized processes, support client communications, and contribute to a seamless overall client experience.

This is a full-time hybrid position reporting to our office located in Ann Arbor, MI.

• Support Account Managers with day-to-day servicing of small group employee benefits clients.
• Assist in the renewal process by gathering data, preparing proposals, and reviewing plan options.
• Process enrollments, terminations, and benefit changes with carriers and vendors accurately and efficiently.
• Respond to client inquiries related to benefits, billing, eligibility, and claims in a timely and professional manner.
• Maintain accurate and up-to-date client records within agency management systems.
• Prepare client-facing materials, including spreadsheets, presentations, and benefits summaries.
• Coordinate with insurance carriers to resolve issues and ensure timely follow-up on outstanding items.
• Assist with compliance-related tasks and documentation, including ACA requirements.

• 1-2 years of experience in an administrative or office support role.
• Interest in pursuing a career in employee benefits and obtaining a Life & Health insurance license.
• Strong organizational skills with high attention to detail and accuracy.
• Excellent written and verbal communication skills.
• Proficiency in Microsoft Office Suite, including Excel, Outlook, and Word.
• Ability to manage multiple priorities and meet deadlines in a fast-paced environment.
• Strong interpersonal skills with the ability to collaborate effectively within a team.
• Commitment to providing high-quality service and maintaining professionalism in all interactions.

Founded in 2019, Patriot is a growth-focused national insurance services firm that partners with employee benefits and property and casualty agencies across the United States. Patriot is currently ranked as the 25th largest broker in the U.S. by Business Insurance and has been named to the 2025 Inc. 5000 list of fastest-growing companies. With over 2,100 employees operating in 150+ locations in over 45 states, Patriot’s collaborative model delivers resources and strategic support to its agencies.

Patriot creates true alignment with its partner agencies, and its operating philosophy fosters enhanced career opportunities for its dedicated and professional team. We are committed to working with like-minded individuals who share our vision of creating an insurance agency focused on operational excellence and a relentless pursuit of growth.

Patriot offers the opportunity to be a part of a fast-growing company since its inception. We strive to create a flexible and collaborative environment for our employees, and our goal is to provide continual learning and enhanced career opportunities for our dedicated, professional team.

In addition to a competitive salary, we provide a comprehensive health and welfare program to employees, family members and domestic partners. Employees are eligible for benefits coverage the first of the month following 30 days of employment. We offer:

• Medical, Dental, and Vision Benefits Flexible Spending Account (FSA) and Health Savings Account (HSA) and…