Manager, Product Design

Summary

Join HopSkipDrive's Product Design team as a Manager of Product Design, leading and mentoring a high-performing team while ensuring high-quality, user-centered design solutions. You will balance strategic vision with hands-on design contributions, collaborating with various teams to align design efforts with business objectives. Champion user advocacy, lead design reviews, and optimize design processes. Monitor the impact of design initiatives and guide the design of AI-powered features, prioritizing human control and trust. This role requires a player-coach mentality, combining design excellence with mentorship and strategic thinking, and a passion for translating complexity into clarity, especially in enterprise or B2B environments. HopSkipDrive offers equity, flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and the opportunity to work for a VC-backed company.

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

• Every full-time employee has equity
• Flexible vacation
• Medical, dental, vision and life insurance
• 401(k)
• FSA
• The base salary range for this role is $160,000 - $185,000
• The total compensation package for this role also includes equity stock options