Compliance & Legal Operations Manager

About the Company

At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation, connecting kids to highly-vetted caregivers on wheels through our marketplace and software.

Responsibilities

• Lead compliance analysis for new and existing state markets and develop state-specific documentation
• Act as the primary point of contact for school districts on compliance and regulatory questions
• Serve as the platform owner for Ironclad, configuring workflows and maintaining integrations
• Own contract metadata extraction and track terms in ClickUp and master tables
• Lead outside counsel management by reviewing vendor invoices and optimizing legal spend
• Partner on data privacy, SOC 2 maintenance, and vendor risk reviews
• Manage legal-specific AI tool licensing, onboarding, and feature rollouts
• Build and iterate on compliance dashboards, intake chatbots, and automated tech stack solutions

Requirements

• 4–7 years of experience in compliance, legal operations, or a highly regulated field
• Proven hands-on experience administering and configuring Ironclad workflows
• Demonstrated track record of leveraging generative AI tools to accelerate workflows
• Strong capability to analyze complex, state-level regulatory frameworks
• Proven ability to manage concurrent workstreams across different states and stakeholders
• Experience establishing and scaling operational legal systems
• Experience drafting professional documentation and interfacing with external clients

Benefits

• Equity stock options
• Flexible vacation
• Medical, dental, vision, and life insurance
• 401(k) and FSA