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HopSkipDrive

Director of Legal, Product and Regulatory Compliance

Job Summary

This role involves providing legal advice and guidance to support the company's growth, innovation, and compliance efforts. The candidate should have extensive experience in regulatory compliance and legal management, with the ability to manage cross-functional projects and communicate complex legal topics clearly. Responsibilities include ensuring products meet legal standards, staying updated on legal changes, and fostering a culture of compliance within the organization. The position offers opportunities to work in a fast-paced environment with a focus on strategic legal support and team development.

Required Skills

Cross-functional Collaboration
Project Management
Regulatory Compliance
Legal Education
Legal Strategy
Legal Advice
Legal Writing
Legal Communication
Legal Management
Legal Planning

Benefits

Medical Insurance
Dental Insurance
Vision Insurance
Life Insurance
Flexible Vacation
Equity/Stock Options
401(k)
FSA

Job Description

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


The Legal team works hand-in-hand with leaders across the company to support HopSkipDrive’s growth, innovation, and strategic initiatives. It's an integral and highly impactful team that provides legal advice and guidance to ensure the company operates within legal boundaries while protecting intellectual property, financial interests, and regulatory compliance. We navigate complex legal landscapes to mitigate risks and support innovation. This is an exciting opportunity to learn in a fast-paced environment and own high-priority projects.

  • Work with a team of lawyers and legal professionals to ensure that products meet all applicable local, state, and federal laws and regulations. This includes staying up-to-date on changes in relevant legislation and advising on how to adapt business practices accordingly.
  • Serve as a “player coach” to develop the bench of legal talent advising the company on product, privacy, and regulatory compliance. You will work to educate internal teams on legal and compliance requirements, helping to foster a culture of compliance within the organization
  • Work closely with cross-functional teams, such as the Policy, Communications, and Operations organizations, in order to provide advice, support their objectives, and set them up for success.

Who You Are

  • 13+ years experience as an attorney with a depth of knowledge in regulatory compliance
  • Experience managing personnel, especially attorneys or other professionals, with a proven ability to communicate clear goals and expectations and hold a team accountable to meeting those goals
  • Proven ability to project manage cross-functional projects and make complex decisions by gathering cross-functional input
  • Strong writing and verbal communication skills with keen attention to detail, including a proven ability to distill complex topics into easy-to-understand guidance for non-legal teams and an ability to clearly communicate reasons behind trade-off decisions
  • Ability to evaluate complex regulations to identify compliance requirements, business opportunities, and areas where additional legal advice may be required
  • Proven ability to build and facilitate implementation of compliance requirements, setting up systems and processes to ensure compliance
  • Ability to keep finger on the pulse of regulatory changes and opportunities that could impact HopSkipDrive operations
  • Proven ability to communicate and execute strategic plans to achieve functional and organizational objectives



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 proud to operate as a drug-free workplace. HopSkipDrive is also committed to fair and equitable compensation practices. The salary range for this role in Los Angeles, CA is $190,000.00- $200,000.00. 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 AZ, CA, CO, CT, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI**

Interested in this job?

Application deadline: Open until filled

Logo of HopSkipDrive

HopSkipDrive

HopSkipDrive is the leading provider of supplemental student transportation and routing software, all powered by transformative technology.

See more jobs
Date PostedJuly 17th, 2025
Job TypeFull Time
LocationRemote
Salary$190,000 - $200,000
Exciting fully remote opportunity for a Director of Legal, Product and Regulatory Compliance at HopSkipDrive. Offering $190,000 - $200,000 (full time). Explore more remote jobs on FlexHired!

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