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Director of Compliance & Litigation

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Fast Facts

The Director of Compliance & Litigation at HopSkipDrive will lead compliance efforts and manage litigation for a growing transportation network company focused on education, ensuring adherence to regulatory requirements and fostering collaboration across teams.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Responsibilities: Develop and implement compliance policies, manage litigation, conduct audits, provide legal counsel, and serve as a subject matter expert on TNC and DOE regulations.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Skills: Proven experience in compliance and litigation, exceptional analytical and organizational skills, and the ability to adapt to a fast-paced regulatory environment are essential.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Qualifications: Juris Doctor (JD) with 10+ years in compliance and 5+ years in litigation, with relevant experience in school districts or transportation network regulations.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Location: This position is fully remote but candidates must reside in specific states within the US.

liETtVLaARqgmMEbYzHNNLIzUPcdfPrwhYtVK7Qa.png Compensation: $180000 - $200000 / Annually




Who We Are

HopSkipDrive Legal is a team of lawyers and legal professionals dedicated to excellent client service. We are a key resource to our business partners, with the responsibility for protecting and representing the company’s interests and maintaining the company’s compliance with laws, rules, and regulations, all while building efficient, sustainable legal systems for our rapidly growing company.

Who you are

You are looking for a challenging and rewarding experience. You are inspired by our vision and the opportunity to define a new category in an incredibly fast-growing market. You are excited to learn, grow and collaborate so we can achieve our mission of creating opportunity for all through mobility.

At HopSkipDrive, we know that challenges require different approaches, unique perspectives and new ways of thinking. We are building a team of creative problem-solvers from many different backgrounds.

As Director of Compliance & Litigation, you will be highly motivated to organize and push forward compliance requirements for HopSkipDrive as a transportation network company working in the education sector, and help manage our growing book of litigation and claims. You will:

  • Have proven experience managing a compliance program either in-house or as a go-to resource for clients as outside counsel. 
  • Have experience presenting to leadership and c-suite. 
  • Experience providing legal advice and recommendations to the business side of an organization. 
  • Provide expert legal advice regarding day-to-day company compliance related to transportation network company (TNC) regulations and regulations applicable to work with minors (i.e., Department of Education (DOE); National Child Protection Act (NCPA), etc.).
  • Develop, implement, and maintain compliance policies and procedures specifically tailored to TNC and DOE regulations.
  • Supervise compliance managers tasked with day-to-day market- or client-specific compliance management. 
  • Conduct regular audits and assessments to ensure adherence to applicable regulations and identify areas for improvement.
  • Collaborate with cross-functional teams including legal and operations to address compliance issues and implement solutions.
  • Stay abreast of changes in TNC and DOE regulations, and proactively communicate relevant updates to key stakeholders.
  • Provide training and support to internal teams to promote compliance awareness and understanding.
  • Provide strategic counseling to cross-functional business partners on existing and new services with a lens toward understanding and quantifying potential risk in order to help the business make informed decisions.
  • Serve as a subject matter expert on TNC and DOE regulations, providing guidance and advice to senior management as needed.

What We’re Looking For

  • A candidate who wants to efficiently manage a growing startup compliance portfolio
  • JD & 10+ years experience in compliance and 5+ years in litigation 
  • Legal experience in either a school district, transportation network company or regulations impacting work with minors required
  • Proven ability to manage internal audit procedures 
  • Proven ability to facilitate implementation of compliance requirements, setting up systems and processes to ensure compliance
  • Experience managing people
  • Exceptional analytical skills with the ability to interpret complex regulatory requirements and apply them to practical business operations
  • Exceptional organizational skills
  • Detail-oriented with a high degree of accuracy in documentation and reporting
  • Ability to adapt to a fast-paced and evolving regulatory environment

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 committed to fair and equitable compensation practices. The base salary range for this role is $180,000 - $200,000. 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.

HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.

* This role will be fully remote in one of the following states in which we actively hire in: AZ, CA, CO, CT, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OH, OK, OR, SC, TN, TX, UT, VA, WA, WI**

HopSkipDrive Glassdoor Company Review
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CEO of HopSkipDrive
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Joanna McFarland
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Average salary estimate

$190000 / YEARLY (est.)
min
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$180000K
$200000K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

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Our mission is to give all kids access to opportunity through mobility.

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BENEFITS & PERKS
Dental Insurance
Flexible Spending Account (FSA)
Health Savings Account (HSA)
Vision Insurance
FUNDING
SENIORITY LEVEL REQUIREMENT
TEAM SIZE
EMPLOYMENT TYPE
Full-time, remote
DATE POSTED
November 2, 2025
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