Sr. Product Designer
Role summary
HopSkipDrive is seeking a Senior Product Designer to lead complex, high-visibility design initiatives for their marketplace and software solutions. This role involves crafting user-centered experiences, defining design systems, and integrating AI into product features. The designer will mentor junior team members, conduct user research, and collaborate with Product and Engineering teams. Key responsibilities include contributing to product strategy, ensuring design consistency, and communicating design rationale to executive stakeholders. The ideal candidate has 5+ years of experience, advanced UX/UI skills, proficiency in design systems and AI tools, and a strong understanding of accessibility and user research.
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
Our Product Design team is at the forefront of crafting intuitive, impactful, and user-centered experiences that power our innovative marketplace and software solutions. We're passionate about high standards of design craft and accessibility, and we thrive on deep collaboration with our Product, Engineering, and Data teams. As we evolve, we're keenly focused on how AI integration will reshape user journeys, transparency, control, and trust within our emerging products. We're seeking a Senior Product Designer to lead complex, high-visibility design initiatives, raise the bar on design craft, and help pioneer new levels of design excellence. Our work spans high-stakes enterprise tools, dynamic consumer mobile applications, and robust internal systems, all unified by our unwavering commitment to safety, empathy, and intelligent simplicity.
As a Senior Product Designer, you will take the lead on complex design projects that significantly impact HopSkipDrive's usability and visual appeal. You will create end-to-end design solutions, from conceptual exploration to detailed interaction design, while advocating for user needs throughout the development process. You are expected to provide mentorship to junior designers and leverage user feedback and data to make informed design decisions that align with business goals. You'll:
Who You Are
You are a design leader who blends advanced craft with strategic thinking and a passion for mentorship. You bring a systems-thinking mindset, strong UX instincts, and a track record of translating complexity into clarity — especially in enterprise or B2B environments.
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 salary range for this role is $135,000 - $163,000. 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 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**
