Compliance & Legal Operations Manager

At HopSkipDrive , our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country. Founded by three moms as a solution to their own transportation challenges, we've now facilitated more than five million rides across over over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date. How we work We're an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don't expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward. We're remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar. Who We Are Our lean, high-trust Legal & Compliance team is foundational to HopSkipDrive's expansion, directly managing the multi-state regulatory infrastructure and operational systems that power our growth. We support the business and build scalable programs through the following primary responsibilities: Regulatory Research & Market Expansion: Lead compliance analysis for new and existing state markets and develop state-specific documentation Client-Facing Compliance Support: Act as the primary point of contact for school districts on compliance and regulatory questions. Ironclad System Administration: Serve as the platform owner for Ironclad, configuring workflows, maintaining integrations with Salesforce/Airbase, and driving internal process documentation. Contract Data & Repository Management: Own contract metadata extraction, define data models, and track terms in ClickUp and master tables to ensure renewal readiness. Legal Operations and Financial Oversight: Lead outside counsel management by reviewing vendor invoices and establishing billing discipline to optimize external legal spend. Risk Review & Policy Development: Partner on data privacy, SOC 2 maintenance, and vendor risk reviews while drafting internal legal guidelines and compliance SOPs. AI Tool Administration: Manage legal-specific AI tool licensing, seats, onboarding, and new-feature rollouts as the team's primary technical resource. AI-Assisted Workflow Automation: Identify workflow leverage areas to build and iterate on compliance dashboards, intake chatbots, and automated tech stack solutions. Who You Are You are a collaborative, tech-forward professional who thrives at the intersection of regulatory complexity and emerging technology, ready to build systems that scale. You bring the following essential experiences and mindsets to our team: Regulated Industry Experience: 4–7 years of dedicated experience in compliance, legal operations, or a closely related highly regulated field. Ironclad Mastery: Proven hands-on experience administering and configuring workflows within the Ironclad contract lifecycle management platform. Technical Adaptability & AI Agility: Demonstrated track record of independently adopting, administering, and leveraging generative AI tools to accelerate professional workflows. Regulatory Research Skills: Strong capability to analyze complex, state-level regulatory frameworks and synthesize them into clear, actionable resources. Multi-Project Management: Proven ability to manage concurrent workstreams across different states, issue types, and cross-functional stakeholders simultaneously. Process & System Building: A foundational background in establishing, scal