Compliance & Legal Operations Manager (Transportation)

TL;DR

Compliance & Legal Operations Manager (Legal Ops): Managing multi-state regulatory infrastructure and operational systems for a student transportation marketplace with an accent on regulatory research, CLM administration, and AI-assisted workflow automation. Focus on scaling compliance programs, optimizing external legal spend, and implementing generative AI tools to accelerate legal workflows.

Location: Must reside in and perform work from one of the following US states: AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, or WI.

Salary: $110,000 – $115,000

Company

A leader in safe supplemental student transportation using a software marketplace to connect schools with vetted caregivers.

What you will do

• Lead compliance analysis for new and existing state markets and develop state-specific documentation.
• Administer the Ironclad CLM platform, configuring workflows and maintaining integrations with Salesforce and Airbase.
• Own contract metadata extraction and track renewal terms using ClickUp and master tables.
• Manage outside counsel by reviewing vendor invoices and establishing billing discipline to optimize spend.
• Partner on data privacy, SOC 2 maintenance, and vendor risk reviews while drafting compliance SOPs.
• Manage legal-specific AI tool licensing and build automated solutions like intake chatbots and compliance dashboards.

Requirements

• 4–7 years of experience in compliance or legal operations within a highly regulated field.
• Hands-on experience administering and configuring workflows in Ironclad.
• Must be based in one of the specified US states.
• Strong ability to analyze complex state-level regulatory frameworks.
• Proven track record of leveraging generative AI tools to accelerate professional workflows.
• Experience drafting high-stakes documentation and interfacing with external clients or district partners.

Culture & Benefits

• Equity stock options provided to all full-time employees.
• Flexible vacation policy and comprehensive medical, dental, vision, and life insurance.
• 401(k) and FSA benefits.
• Remote-first environment within an AI-forward company culture.
• Opportunity to work in a VC-backed Series D company with significant growth potential.