Administrative Assistant at Diversified Benefit Services – Hartland, Wisconsin

Where precision meets purpose.
Are you energized by details, motivated by accuracy, and driven to support a team that depends on you? Do you enjoy working with numbers, systems, and processes — while still building strong relationships internally and with clients?
If you thrive in a fast-paced, service-oriented environment where learning is continuous and your work truly matters, this could be your next move. We’re looking for a polished, highly organized Administrative Assistant to play a critical role in supporting our daily operations. From financial reconciliation to benefit plan enrollments, you’ll be at the center of activity — trusted with high-visibility responsibilities from day one.

What You’ll Do
You’ll serve as an administrative backbone to the organization, supporting multiple departments while ensuring accuracy, compliance, and exceptional client service.

Financial & Billing Operations

• Develop strong working knowledge of billing processes and invoicing nuances that may affect client invoicing.
• Generate monthly client invoices utilizing internal spreadsheets and QuickBooks.
• Perform invoicing audits.
• Respond to client invoicing inquiries.
• Generate monthly statements, identify past-due accounts and send notifications to clients.

Benefits Administration Support

• Work directly with clients to coordinate annual Flexible Spending Account (FSA) enrollments.
• Prepare an effective tracking system to ensure that all enrollments are received, entered and audited by plan deadlines.
• Coordinate distribution of FSA and HSA enrollment materials.
• Work directly with Data Analysts on the import of enrollment data files.
• Regularly evaluate and provide input on process improvements to gain efficiency and increase accuracy of enrollments.

Administrative Support

• Serve as backup for reception as needed.
• Send out W-9 Forms as requested by clients.
• Generate and process quarterly agent commission reports and issue payments.
• Assist with Form 5500 filing process.
• Generate and track annual client renewal letters for all benefit plans administered.
• Coordinate distribution of non-discrimination testing materials to clients, assist with client questions, run tests and work directly with Compliance Department to work through test failures.

This role offers exposure to financial operations, employee benefits administration, client services, and cross-functional collaboration.

What We’re Looking For

• Mid to high-level competency in MS Office Suite of products.
• Exceptional oral and written communication skills.
• Strong numbers aptitude.
• Outstanding organizational and analytical skills, meticulous attention to detail and thorough follow through skills are critical.
• Professional interpersonal skills, high degree of confidentiality, self-motivation with the ability to effectively manage multiple tasks and prioritize without sacrificing quality.
• Ability to identify, resolve and escalate issues.
• Proven successful experience in a fast-paced, deadline driven environment that involved high detail orientation and strong multi-tasking skill.

Preferred Work Skills

• Prior experience in financial services, benefits, human resources or related industries.
• Experience working in QuickBooks or similar software.

Who We Are
For nearly 40 years, Diversified Benefit Services (DBS) has been a trusted third-party administrator specializing in FSAs, HRAs, ICHRAs, HSAs, COBRA, and customized benefit solutions.
We believe our people are our greatest asset. We invest in training, provide innovative tools, and create an environment where motivated professionals can build meaningful careers. At DBS, you won’t just support operations — you’ll strengthen them.

If you're looking for a role where precision, collaboration, and continuous learning come together, we’d love to meet you. https://diversifiedbenefitservices.applytojob.com/apply

If this role sounds like a fit, we'd love to hear from you. Apply now.