Jobs · Legal

Administration & Compliance Manager

160 Driving Academy · Chicago, IL · 1 wk ago
RemoteRemoteLegalFull-time

Description MORE THAN A JOB. A CAREER THAT CHANGES LIVES. 160 Driving Academy is the largest CDL training school in the country — 14 years strong, 90+ locations across 32 states, and roughly 20,000 students earning their commercial driver's license with us every year. We graduate at an 88% first-time pass rate because we take the work personally. Behind every one of those graduates is a working adult who chose to bet on themselves—a parent looking for stable income, a veteran starting a second career, a worker pivoting out of an industry that was no longer hiring. They picked up the phone, called us, and someone on the other end of the line treated their question like it mattered. None of it happens without licenses. Operating 90+ locations across 32 states means hundreds of business licenses, school approvals, renewals, and regulatory relationships—every one of them with a deadline attached. The Administration & Compliance Manager is the person who sees every one of those deadlines coming and handles it before it becomes a problem. That someone is you.

About The Administration & Compliance Manager Role

As Administration & Compliance Manager, you help drive the administrative backbone of 160's regulatory footprint. You work directly with state department representatives and municipalities on renewals, business licenses, and approvals; you track every license expiration across the network and stay ahead of it—months ahead, not days. You report to the National Director of Compliance and serve as their research arm, tracking system, and execution engine. This is a pseudo-paralegal role for a natural organizer and fact-finder. You research compliance obligations, track them to resolution, dig for the right answer when the regulation is ambiguous, and keep documentation clean and audit-ready.

Familiarity with the Federal Motor Carrier Safety Administration (FMCSA), Entry-Level Driver Training (ELDT) requirements, and adult-education regulatory frameworks will make you effective on day one. The role is fully remote with flexible hours. What matters is that renewals are filed early, regulators are answered promptly, and nothing—ever—lapses on your watch as it has big impact on the business.

What You'll Do As The Administration & Compliance Manager

  • Licensing & Renewals
    • Own the master license and renewal calendar across 90+ locations in 32 states—business licenses, school approvals, and operating permits
    • Track license expiries and see ahead of them—flag, prepare, and file renewals well before deadlines
    • Work directly with state department representatives and municipalities on renewals, applications, and approvals
    • Build durable working relationships with regulators so questions get answered and issues get resolved early
    • Keep every filing, approval, and certification organized, current, and audit-ready
  • Compliance Research & Tracking
    • Research and track compliance obligations like a paralegal—fact-find, document, summarize, and flag what matters
    • Monitor FMCSA and Entry-Level driver training (EDLT) requirements as they evolve
    • Track adult-education regulatory requirements state by state and translate then into action items
    • Build and maintain tracking systems in the Office suite so nothing slips through
    • Support the Director of Compliance on audits, regulator inquiries, and special projects

Requirements

  • Undergraduate degree
  • Tech-savvy and strong with Office suite technology—Excel, Word, Outlook, SharePoint
  • Exceptional organizer: builds tracking systems, follows through, and never lets a deadline surprise the team
  • Research and fact-finding instincts—comfortable digging into regulations and getting to a clear answer
  • Accountable, self-directed, positive energy—thrives working remote with flexible hours

Prior Experience

  • Prior experience as a senior executive assistant or in an organizing-executor role
  • Experience with the Federal Motor Carrier Safety Administration (FMCSA), transportation, CDL, or commercial driving training
  • Entry-Level Driver Training (ELDT)
  • Adult-education regulatory requirements experience
  • Paralegal training or experience working in a legal capacity

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