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 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, scaling, and continuously improving operational legal systems and organizational frameworks.
• External Partner Communication: Experience drafting high-stakes professional documentation and interfacing directly with external clients or district partners.

Our Investment In You

We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role in Los Angeles, CA is $110,000.00 - $115,000.00. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.