Manager, Product Design

HopSkipDrive

155d • $160,000 - $185,000

About The Position

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.

Requirements

• 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.

Responsibilities

• 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.

Benefits

• Equity for every full-time employee.
• Flexible vacation.
• Medical, dental, vision, and life insurance.
• 401(k).
• FSA.
• Opportunity to work for a uniquely positioned, VC-backed company.

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Number of Employees: 251-500 employees