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
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 visionary design leader to help us elevate our team, guide exceptional design execution, and 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 Manager of Product Design, you’ll be a pivotal leader, combining strategic vision with hands-on excellence. Specifically, you will:
- Lead & Mentor: Inspire, grow, and develop a high-performing team of product designers, fostering a collaborative, supportive, and growth-oriented culture.
- Drive Design Excellence: Provide clear guidance and constructive feedback, ensuring the delivery of high-quality, user-centered design solutions across critical product areas.
- Balance Leadership & Craft: Oversee day-to-day design execution while balancing hands-on design contributions with strategic team leadership and initiatives.
- Drive Cross-Functional Alignment: Collaborate closely with Product Management, Engineering, Data and stakeholders to ensure design efforts are deeply aligned with business objectives and user needs.
- Champion User Advocacy: Actively champion user-centered design principles, accessibility standards, and design best practices throughout the organization.
- Facilitate & Communicate: Lead design reviews, critiques, and presentations, effectively communicating design rationale and decisions to diverse stakeholders.
- Optimize & Innovate: Identify and implement opportunities to continuously improve design processes, tools, and team workflows, driving efficiency and fostering innovation.
- Measure Impact: Monitor and report on the impact of design initiatives, ensuring solutions are robustly informed by user research, data analytics, and continuous feedback loops.
- Shape AI-Powered Experiences: Guide the design of AI-powered features, demonstrating a strong intuition for leveraging automation while prioritizing human control, transparency, and trust.
Who You Are
You are a player-coach design leader who balances hands-on excellence with mentorship and strategy. You enjoy diving into the details within tools like Figma, but your true passion lies in developing others, connecting the dots across complex product ecosystems, and setting a consistently high standard for how design influences cross-functional collaboration. You are passionate about craft, not for its own sake, but because you know small details make big experiences. You bring a systems-thinking mindset, strong UX instincts, and a passion for translating complexity into clarity — especially in enterprise or B2B environments.
- 7+ years of product design experience, with 2+ years leading or managing designers.
- A strong portfolio that demonstrates end-to-end product thinking, craft, and impact across mobile and web platforms.
- Proven track record of delivering intuitive and elegant user experiences for web and mobile.
- Demonstrated success in building, mentoring, and scaling diverse, high-performing design teams, coupled with a genuine growth mindset and a desire to elevate others through constructive feedback, coaching, and shared critique.
- Deep expertise in user-centered design processes, usability best practices, and accessibility standards.
- A strong ability to leverage data and research—not just for validation, but to uncover hidden user needs, shape strategic direction, and tell compelling stories that drive superior product decisions.
- Hands-on experience designing AI-powered features, with a sophisticated understanding of when to embrace automation and when to ensure human oversight.
- Exceptional communication and storytelling skills, with the ability to influence and align stakeholders at all levels of the organization.
- A collaborative spirit, eager to partner closely with product managers, engineers, and stakeholders to define product strategy and deliver impactful solutions.
- Proficiency with modern design and prototyping tools (e.g., Figma), along with a solid understanding and experience with design systems and scalable design practices.
- Ability to balance strategic vision with hands-on execution in a fast-paced, growth-oriented environment.
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 base salary range for this role is $160,000 - $185,000. 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, 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**
