Fleet Compliance Associate

Drivewyze by Fleetworthy; Madison (WI); On-site; USD 52,000 - 78,000; Full time

Job summary

Fleetworthy in Madison, WI seeks a detail-oriented Compliance Support Specialist to help keep carrier clients compliant. You will perform daily data validation, answer questions, resolve issues, and serve as a trusted point of contact for assigned clients.

You'll work with a capable management team and learn the intersection of transportation regulation and technology, with comprehensive training and clear opportunities for growth within the company.

Qualifications

• 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.

Responsibilities

• 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

Skills

Strong communication

Client management

Organizational skills

Attention to detail

Time management

Tools

Microsoft 365

Word

Excel

Job description

Fleetworthy offers the only complete technology suite for fleet readiness, uniting safety and compliance, toll management, and weigh station bypass solutions. We help fleets streamline operations, control costs, an d opera te with confidence. Trusted by 75% of the top fleets in North America, Fleetworthy offers the most adopted toll management solution and largest weigh station bypass network. Going beyond regulatory requirements, our safety and compliance capabilities strengthen safety programs and enable proactive audit readiness. We support millions of vehicles and drivers and are recognized across the industry for innovation and leadership. Fleetworthy is shaping the future of fleet readiness with AI-enabled, connected fleet technology that keeps drivers safe, fleets compliant, and operations running at peak efficiency. Learn more at fleetworthy.com .

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)

Fleetworthy is committed to fostering a diverse and inclusive culture that is respectful and welcoming of individual differences. We are proud to be an equal opportunity employer and all qualified applicants will receive consideration for employment without regard to race, color, religion or belief (or lack thereof), sex, nationality, national or ethnic origin, civil status, age, citizenship status, sexual orientation, disability, genetic information, familial status, marital or registered civil partnership status, pregnancy or maternity status, gender identity, gender reassignment, military or veteran status, or any other protected characteristic in accordance with applicable laws and regulations.