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:
- Lead Strategic Design Initiatives: Contribute to product design vision and strategy, applying systems thinking to complex challenges and leading design initiatives that address strategic product opportunities across HopSkipDrive's portfolio.
- Define Patterns & Consistency: Define UX patterns and ensure consistency across products, developing and implementing scalable design systems and components with strong proficiency in design tools, prototyping, and accessible design.
- Drive Research-Informed Decisions: Conduct strategic design research to identify long-term opportunities, integrate user research and data analysis into strategic product decisions, and synthesize complex findings into clear, actionable insights.
- Lead AI-Accelerated Discovery: Lead discovery phases using AI tools to synthesize research at a speed and depth not possible manually, bringing sharper, data-backed rationale into cross-functional design strategy conversations, and evaluating which design problems are strong candidates for AI-powered solutions.
- Design AI-Powered Features: Design high-quality AI-powered product features with well-defined interaction patterns, error states, and edge cases — bringing a discerning eye to AI tool outputs and iterating with intent.
- Mentor & Elevate the Team: Mentor other designers, facilitate design workshops and critiques, foster a collaborative design culture, and help establish team norms for effective, critical use of AI tools.
- Communicate & Influence: Communicate and defend design rationale to executive stakeholders and cross-functional teams, facilitate cross-functional workshops to drive alignment, and present design strategy and vision to senior stakeholders.
- Own Design Outcomes: Own design outcomes for significant product areas, define and measure success in terms of business and user metrics, and drive measurable customer impact through well-designed AI experiences — reducing friction, improving personalization, and increasing user confidence.
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.
- 5+ years of product design experience, with a track record of leading complex, cross-functional design initiatives end to end.
- Advanced UX/UI design skills with a focus on holistic user experiences, strong visual execution, and proficiency in end-to-end design.
- Experience establishing and maintaining design standards, best practices, and scalable design systems for a team.
- Proven ability to lead complex prototyping and usability testing efforts, ensuring high-quality, accessible results across multiple product areas.
- Demonstrated ability to integrate user research and advanced data analysis into strategic product decisions, and to lead research initiatives that inform roadmap and strategy.
- Experience in designing for mobile and web platforms
- Experience mentoring designers, facilitating critiques and workshops, and fostering a collaborative, user-centered design culture.
- Exceptional communication skills, with the ability to defend design rationale to executive stakeholders and build strong relationships across the organization.
- Hands-on experience using AI tools to accelerate discovery, research synthesis, and prototyping — with the judgment to know when AI interpretation is reliable and when human judgment must lead.
- A discerning eye for AI-generated design output, consistently iterating with intent and creating new skills or workflows to increase team efficiency and consistency.
- Proficiency with modern design and prototyping tools (e.g., Figma), along with solid understanding of design systems and scalable design practices.
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**