Back to jobs

Director, Legal Risk & Regulatory Strategy

Remote - US

At HopSkipDrive, our goal is to create opportunity for all through mobility. 

We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts around the country. 

Founded by three moms as a solution to their own transportation challenges, we’ve now facilitated more than five million rides across over 17 states around the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date.

Who We Are

HopSkipDrive's Legal & Regulatory team is scaling rapidly to support the next phase of company growth, operational complexity, and national expansion. As a transportation network company operating in a highly regulated and safety-critical environment, we are building the foundational systems, strategic insights, and compliance infrastructure that will support multi-state scale.

As Director, Legal Risk & Regulatory Strategy, you will help architect these systems. You will shape how a fast-growing technology company proactively manages litigation, aligns regulatory strategy with product and operations, and builds durable frameworks that support long-term scalability.

You will:

  • Build and lead the strategic roadmap for regulatory compliance across TNC and education-focused requirements, ensuring we scale responsibly and efficiently.
  • Own the company’s litigation and claims portfolio, building systems for early risk detection, streamlined management, and high-quality outcomes.
  • Partner deeply with senior leadership, Product, Operations, and cross-functional teams to anticipate regulatory shifts and inform company-wide strategy.
  • Develop and operationalize compliance programs, policies, audits, and controls in a way that is built for scale and automation—not manual lift.
  • Lead, mentor, and grow a team of compliance managers focused on market-level or client-specific compliance operations.
  • Build repeatable, data-driven processes for monitoring regulatory change, surfacing insights, and enabling leadership decision-making.
  • Serve as a subject-matter expert on TNC and DOE regulations, ensuring alignment between emerging business models and the regulatory landscape.
  • Drive cross-functional initiatives that reduce operational risk, strengthen governance, and prepare the organization for multi-state and multi-product growth.

Who You Are

You are a strategic legal and regulatory leader who thrives in high-growth environments where the challenge is to build what does not yet exist. You are energized by solving complex systems problems, navigating ambiguity, and creating scalable frameworks that enable innovation. You bring the depth of experience needed to shape company-wide regulatory strategy, paired with the agility to operate in a fast-moving, scaling tech environment.

With the following experience, you’ll make an immediate impact:

  • 10+ years of legal experience, with significant expertise in compliance and at least 5 years managing litigation or claims portfolios.
  • Demonstrated success designing and operationalizing compliance systems in a fast-growing or multi-jurisdictional environment—Big Tech or highly regulated tech preferred.
  • Experience advising executives and influencing strategy in environments where regulatory requirements intersect with product, operations, and growth.
  • Deep understanding of TNC, DOE, or other regulatory frameworks involving minors—or the ability to quickly become a subject-matter expert.
  • Proven ability to manage audits, implement governance controls, and translate complex regulations into practical business processes.
  • Experience building and leading teams, with an orientation toward systems, empowerment, and scalable processes.
  • Highly analytical, a strong communicator, and comfortable operating at both strategic and tactical levels.
  • A bias for action and adaptability as regulations, markets, and the business evolve rapidly.

Create a Job Alert

Interested in building your career at HopSkipDrive? Get future opportunities sent straight to your email.

Apply for this job

*

indicates a required field

Resume/CV*

Accepted file types: pdf, doc, docx, txt, rtf

Cover Letter

Accepted file types: pdf, doc, docx, txt, rtf

Select...
Select...
Select...
Select...
Select...
Select...
Select...
Select...

You acknowledge that by participating in the interview process with HopSkipDrive, you may be provided with information that is not publicly available (Confidential Information). You agree and represent that you will not make use of nor disclose to any third party any of the Confidential Information until it becomes publicly known or made generally available through no fault of your own. Confidential Information includes nonpublic information relating to products, services, marketing plans, business policies, practices, and strategies; organization and employee and hiring information; inventions, formula, code, and technical information; trade secrets; research; financial information; customer information; information received from third parties that HopSkipDrive is obligated to treat as confidential; and information which by its nature would reasonably be considered Confidential Information.

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in HopSkipDrive’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Select...
Select...
Race & Ethnicity Definitions

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

Select...

Voluntary Self-Identification of Disability

Form CC-305
Page 1 of 1
OMB Control Number 1250-0005
Expires 04/30/2026

Why are you being asked to complete this form?

We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.

Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.

How do you know if you have a disability?

A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:

  • Alcohol or other substance use disorder (not currently using drugs illegally)
  • Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
  • Blind or low vision
  • Cancer (past or present)
  • Cardiovascular or heart disease
  • Celiac disease
  • Cerebral palsy
  • Deaf or serious difficulty hearing
  • Diabetes
  • Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
  • Epilepsy or other seizure disorder
  • Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
  • Intellectual or developmental disability
  • Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
  • Missing limbs or partially missing limbs
  • Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
  • Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
  • Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
  • Partial or complete paralysis (any cause)
  • Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
  • Short stature (dwarfism)
  • Traumatic brain injury
Select...

PUBLIC BURDEN STATEMENT: According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.