Note: The job is a remote job and is open to candidates in USA. HopSkipDrive is a leader in supplemental student transportation, connecting kids to vetted caregivers through their marketplace. The Compliance & Legal Operations Manager will oversee compliance analysis, manage legal operations, and support the business in navigating regulatory complexities while leveraging technology to enhance efficiency.
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, maintaining integrations with Salesforce/Airbase, and driving internal process documentation
- Own contract metadata extraction, define data models, and track terms in ClickUp and master tables to ensure renewal readiness
- Lead outside counsel management by reviewing vendor invoices and establishing billing discipline to optimize external legal spend
- Partner on data privacy, SOC 2 maintenance, and vendor risk reviews while drafting internal legal guidelines and compliance SOPs
- Manage legal-specific AI tool licensing, seats, onboarding, and new-feature rollouts as the team's primary technical resource
- Identify workflow leverage areas to build and iterate on compliance dashboards, intake chatbots, and automated tech stack solutions
Skills
- 4–7 years of dedicated experience in compliance, legal operations, or a closely related highly regulated field
- Proven hands-on experience administering and configuring workflows within the Ironclad contract lifecycle management platform
- Demonstrated track record of independently adopting, administering, and leveraging generative AI tools to accelerate professional workflows
- Strong capability to analyze complex, state-level regulatory frameworks and synthesize them into clear, actionable resources
- Proven ability to manage concurrent workstreams across different states, issue types, and cross-functional stakeholders simultaneously
- A foundational background in establishing, scaling, and continuously improving operational legal systems and organizational frameworks
- Experience drafting high-stakes professional documentation and interfacing directly with external clients or district partners
Benefits
- Equity
- Flexible vacation
- Medical, dental, vision and life insurance
- 401(k)
- FSA
- Opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential
- Equity stock options
Company Overview