Head of Legal Operations

About the RolecircYoulation is a tech-driven logistics and non-emergency medical transportation (NEMT) provider operating across Southeast.We run an automated, data-heavy operation utilizing fleet telematics, specialized compliance systems, and cloud management tools. This is a single-operator, hands-on role—not an executive desk position managing a team. You will directly own, build, and execute our legal operations, state agency compliance, driver contracting, and insurance claims recovery end-to-end.If you are legally literate, analytical, tech-fluent, and have the backbone to hold insurance adjusters and state agencies accountable without backing down, this role is built for you.Key ResponsibilitiesCommercial Subrogation & Downtime Recovery (Loss of Use):Extract dashcam footage, telematics speed/braking logs, and historical trip revenue data to build undeniable liability and loss-of-use evidence packets.Relentlessly negotiate with adverse insurance adjusters to recover 100% of physical damage, repair delays, and commercial fleet Loss of Business Use (downtime) for not-at-fault collisions.Maintain a strict 48-hour follow-up cadence—zero claims get stalled or abandoned.Driver Contracting & Credential Gatekeeping:Manage end-to-end digital onboarding for independent contractors.Audit background checks, 10-panel drug screens, CPR/First Aid certs, and MVRs inside our compliance platform before any driver is cleared for dispatch.Enforce strict compliance blocks—no exceptions or overrides for missing documentation.State Regulatory & Agency Interface:Navigate state portals directly to manage SCDMV vehicle registrations, titles, and South Carolina Office of Regulatory Staff (SC ORS) Class C/E carrier filings.Resolve agency bottlenecks, decal renewals, and regulatory inquiries independently.Data-Backed Grievance Resolution:Investigate member, facility, and contract disputes using GPS telematics, time stamps, and dispatch records.Draft formal, audit-ready written findings and maintain complete compliance logs.Required Tech Stack & SkillsDigital Compliance & Onboarding: Experience managing digital document repositories, automated credential tracking, and applicant onboarding workflows.Cloud & Operations: Advanced Google Workspace (Sheets, Docs, Drive), CRM/automation tools, e-signature platforms.Hardware / Telematics: Comfort pulling and analyzing GPS telematics, speed/braking records, and cloud dashcam footage.Legal & Claims Acumen: Ability to interpret commercial contracts, understand insurance policy language, and draft formal third-party demand letters.Who You AreAutonomous Operator: You do not need daily task management, reminders, or hand-holding. You solve software snags, manage your calendar, and execute objectives independently.Meticulous & Precise (High C): You read every line of the fine print, catch compliance discrepancies instantly, and build clean, mathematically accurate documentation.Assertive & Persistent (High D): You don't accept lowball offers, delay tactics, or bureaucratic runarounds from insurance adjusters. You push through gatekeepers and drive claims to a closed check.Fact-Based Communicator: You rely strictly on hard data, numbers, timestamps, and policy language rather than emotional arguments.Qualifications2+ years of experience in legal operations, insurance claims/subrogation, paralegal support, or transportation compliance.Proven track record operating in a digital, fast-paced, multi-software environment.Available to work full-time core business hours (9:00 AM – 5:00 PM EST).Located in the United States with a dedicated, quiet home-office setup.To be considered, include the phrase 'Audit Ready' at the top of your cover note or application message.