Compliance & Legal Operations Manager

🕒 June 3

🌵 Arizona, California, +24 more states – Remote

🌵 Arizona – Remote 🏄 California – Remote ⛰️ Colorado – Remote 🏛️ District of Columbia – Remote 🐊 Florida – Remote 🌽 Illinois – Remote 🌪️ Kansas – Remote 🎰 Nevada – Remote 🏖️ New Jersey – Remote 🌶️ New Mexico – Remote 🗽 New York – Remote 🌲 North Carolina – Remote 🌪️ Oklahoma – Remote 🌲 Oregon – Remote 🦀 Maryland – Remote 🍂 Massachusetts – Remote 🚗 Michigan – Remote ❄️ Minnesota – Remote 🏰 Missouri – Remote 🌴 South Carolina – Remote 🎸 Tennessee – Remote 🤠 Texas – Remote ⛷️ Utah – Remote ⚔️ Virginia – Remote ☕ Washington – Remote 🧀 Wisconsin – Remote

💵 $110k - $115k / year

⏰ Full Time

🟡 Mid-level

🟠 Senior

🧑‍💼 Attorney / Lawyer

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HopSkipDrive

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2014

🚗 Transport

📚 Education

🏢 Enterprise

💰 $37M Series D on 2022-09

Transport • Education • Enterprise

HopSkipDrive is a leading provider of innovative and scalable school transportation solutions, partnering with schools, districts, and counties to provide safe, reliable transportation for youth. They specialize in providing alternatives to traditional school bus routes, catering to students' non-routine needs, those in foster care, and students with special transportation requirements. HopSkipDrive also supports personalized and small group transportation solutions, and uses RouteWise AI technology for transportation optimization. Their service is known for being 40% more affordable than traditional underutilized bus routes. They also address challenges such as bus driver shortages and provide a flexible network of CareDrivers, ensuring safety and reliability.

📋 Description

• 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.

🎯 Requirements

• 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

• Flexible vacation • Medical insurance • Dental insurance • Vision insurance • Life insurance • 401(k) • FSA • Equity stock options