Compliance & Legal Operations Manager

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 ability to quickly learn and leverage new technologies, including AI tools for workflow automation and efficiency.