Client Service Representative

Bestpass · Madison, Wisconsin (Onsite) · Other

Posted 2026-10-20

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This is a great entry point into fleet compliance and serving the trucking industry. You'll work closely with assigned clients to keep them compliant and confident — handling daily data validation, answering questions, resolving issues, and serving as a trusted point of contact. You'll be supported by a knowledgeable management team and given the tools to grow.

If you're organized, service-minded, and interested in the intersection of transportation regulation and technology, this role is a strong fit.

WHAT YOU'LL DO

Serve as the primary processor for assigned carrier clients — processing and coordinating compliance work, responding promptly and consistently

Build reliable, positive working relationships that clients can count on

Investigate and resolve inquiries and issues related to products and services

Support other customer-facing teams and guide clients through compliance platforms and internal tools; provide coaching as needed

Stay current on federal and state regulations affecting carrier compliance

Perform daily data validation and quality control to proactively catch issues before they reach clients

Collaborate with team members and other departments to share knowledge and improve outcomes

Many team members in this role grow into senior compliance, account management, or operations positions — we invest in promoting from within.

WHAT WE'RE LOOKING FOR

Strong written and verbal communication skills; warm, professional, and results-oriented

Comfortable managing multiple priorities and working with a variety of client personalities

Ability to work independently and exercise good judgment on client matters

Proficiency with Microsoft 365, Word, and Excel

Detail-oriented and comfortable working in a focused, desk-based environment using several SaaS platforms

Adaptable — regulations change, procedures evolve, and you take it in stride

TOOLS YOU'LL USE

You'll work in Fleetworthy's compliance and client management platforms, as well as standard productivity tools including Microsoft 365. Full training is provided — no prior experience with our systems is required.

Schedule: Monday to Friday (8am - 5pm)

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