Senior Counsel – Policy & Regulatory

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🌵 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

💵 $178k - $200k / year

⏰ Full Time

🟠 Senior

⚖️ Legal Counsel / General Counsel

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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

• Own multi-state regulatory compliance obligations for HopSkipDrive as a transportation network company operating in the education sector, including TNC licensing, driver qualification standards, DMV record check requirements, and state-specific transportation regulations. • Draft and submit regulatory filings, advice letters, and compliance attestations to state agencies; track and manage agency review, approval, and disposition. • Advise on revenue contract and RFP provisions with regulatory implications, including background check requirements, reporting obligations, and driver and vehicle standards. • Advise internal stakeholders on regulatory requirements for new market entry and ongoing compliance obligations in existing markets. • Build AI projects and workflows related to regulatory matters. • Monitor and analyze federal and state legislation affecting HopSkipDrive’s operations, with a focus on transportation network companies, school pupil transportation, and automated decision systems. • Develop legal and policy positions on pending legislation; collaborate with the Policy and Government Relations teams to prepare bill analyses, public comments, and engagement strategies. • Assist with bill review and bill drafting in partnership with the Policy team. • Identify legislative trends and develop proactive compliance strategies, particularly around TNC regulation, school transportation, and gig economy classification. • Represent HopSkipDrive’s interests in regulatory rulemakings before state public utility commissions and transportation agencies. • Monitor and manage responses to public records and disclosure requests from state and local agencies. • Leverage AI tools for more efficient legislative analysis. • Oversee a book of claims related to labor and employment claims. • Manage a small number of cases or claims related to civil litigation including discovery strategy, preparing corporate witnesses, and directing litigation defense. • Support outside counsel in preparing for and conducting arbitrations. • Handle subpoenas, service of process, and regulatory investigations, coordinating with outside counsel as appropriate. • Build AI projects and workflows related to litigation. • Manage data use agreements and research partnerships with academic institutions and government agencies. • Provide legal research and rulemaking assistance as needed to support a busy and growing regulatory portfolio. • Serve as a legal subject matter expert on AI and automated decision-making, advising on compliance with emerging state AI legislation and internal AI governance frameworks.

🎯 Requirements

• J.D. from an accredited law school and active license to practice law in the jurisdiction where you live. • 8+ years of legal experience, including at 5 in a law firm or in-house role, with primary focus on regulatory and/or governmental affairs and meaningful exposure to litigation or claims management. • Demonstrated ability to work with AI tools in a legal context and uses AI consistently in their own legal work, whether for contract analysis, legal research and synthesis, matter management, regulatory analysis, or various projects. • Demonstrated experience navigating state regulatory agencies, administrative proceedings, or legislative processes • Proven ability to advise cross-functional teams on legislative and regulatory requirements and the legal implications of policy priorities • Exceptional analytical skills with the ability to interpret complex regulatory requirements and apply them to practical business operations • Excellent written and oral communication skills, with the ability to present information clearly to varied audiences and collaborate effectively across teams • Strong organizational skills and the ability to manage a high-volume, rapidly evolving regulatory portfolio with competing deadlines • Comfort operating in a fast-paced, ambiguous environment — bonus points for experience at a rapidly growing company.

🏖️ 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