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Director, Commercial Law

HopSkipDrive

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What commercial roles keep asking for: SaaS (15%) — counted across their open postings here.

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HopSkipDrive has 11 open roles listed here.

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Preparing for this interview

Interviews for commercial roles keep coming back to SaaS. Practise those questions before you sit with HopSkipDrive.

Questions you are likely to be asked

  1. Why do you want to join HopSkipDrive?
  2. What is your experience with Generative AI? Tell me one thing you learned the hard way.
  3. Tell me about a time you disagreed with your manager. What happened?
  4. Where do you want to be in three years?
  5. What is a weakness you are working on, and how?

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About HopSkipDrive

At HopSkipDrive, our mission is to create opportunity for all through mobility. We're  the leader in safe, fast, and simple supplemental student transportation.  Through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across 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 over 20states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date.

How we work

We use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before.

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. The team is embracing AI as a core part of how we work, and is investing in building AI agents and other legal tech tools to modernize contracting and other legal functions.

What You’ll Do

 

Who You Are

You’re a seasoned attorney with a knack for collaboration and influence, and a proven people manager.  You are looking for an opportunity to serve as a trusted advisor and business partner, fostering strong relationships across the organization and externally.  Reporting to the VP, Legal who leads the company’s legal functions and with the following skills, you’ll make a tangible and immediate impact:

 

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 $189,000.00 - $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, 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**



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Listed on greenhouse · posted 2026-08-24. ApplySarthi collects openings and links to application pages; the role is advertised by HopSkipDrive, not by us.