[Remote] Senior Product Design Manager, Payroll

Note: The job is a remote job and is open to candidates in USA. Gusto is hiring a Senior Product Design Manager to lead design for its Payroll product, setting UX direction and managing a team of designers. The role partners across functions to simplify complex payroll workflows, drive AI and automation initiatives, and build consistent, high-quality experiences for small businesses.

Responsibilities

• Lead end-to-end design for Payroll — shaping experiences that help small businesses pay their teams correctly, on time, and with confidence
• Define and communicate the long-term UX vision for Payroll, and rally multiple teams around it
• Partner with Product, Engineering, Data, Ops and others to set strategy and roadmaps
• Lead product initiatives where AI and automation are central to the user experience, simplifying payroll and reducing manual work without compromising accuracy or trust
• Collaborate with Research and Data to uncover customer insights and translate them into clear, actionable UX priorities
• Influence product and technical roadmaps by advocating for design quality, customer needs, and long-term system health
• Set the quality and judgment standard for all design work — whether AI-assisted or not — including when to push further and when outputs meet the bar
• Define and scale shared patterns, principles, and standards that promote quality, consistency, and velocity
• Manage and grow a team of designers, providing mentorship, clear direction, and hands-on support across the team
• Champion the Payroll experience as the foundation of Gusto's broader People Platform, ensuring seamless integration across Benefits, Time & Attendance, and third-party tools

Skills

• 8–10+ years of product design experience, with at least 3 years leading and managing design teams
• Experience designing in complex domains i.e. financial products, healthcare, or similarly regulated environments
• Experience setting UX direction across multiple teams and influencing product strategy — not just executing on it
• Proven ability to drive alignment across cross-functional partners and represent design in high-stakes, strategic conversations
• Deep systems thinking, with a track record of turning interconnected, complex workflows into experiences that feel simple and intuitive
• Clear, direct communication and storytelling skills, with the ability to explain design decisions and influence partners at all levels
• A genuine bond to Gusto's mission and the needs of small businesses
• Demonstrated ability to assess AI-generated design directions: knowing when to use them, when to override them, and how to raise the quality bar on AI outputs
• Experience leading product initiatives where AI or automation is central to the user experience — including how to represent uncertainty, surface errors gracefully, and preserve user agency when automation gets it wrong, particularly in high-stakes contexts
• Experience leading a team through an AI workflow transition — not just adopting AI personally, but changing how a team works, including establishing new norms and standards

Benefits

• All full-time employees receive equity (RSUs).
• Employees based in Denver, San Francisco, and New York work from the office approximately 2–3 days per week (or more depending on role).
• Toronto, Ontario — remote.

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