Senior Product Design Manager, Payroll

Gusto, Inc.•Toronto, ON

7d•$172,000 - $279,000

About The Position

Gusto is hiring a Senior Product Design Manager to lead design for Payroll, one of its most complex and consequential product areas. The role sets the UX direction for a core product used by hundreds of thousands of small businesses and millions of people, with the goal of making payroll faster, more flexible, and increasingly hands-off while preserving accuracy and trust. The manager will lead a team of designers, define and communicate a long-term UX vision, and partner across Product, Engineering, Research, Data, Operations, Compliance, and other groups. The work includes simplifying complex workflows, leading automation and AI initiatives, mentoring designers, setting standards for AI-assisted design quality, and contributing shared patterns and platform standards across Gusto. The role also champions Payroll as the foundation of Gusto’s broader People Platform, supporting integration with Benefits, Time & Attendance, and third-party tools. Gusto describes its Design organization as a collaborative team of more than 80 people. The company is building an AI-native design organization and expects team members to actively engage with relevant AI tools. Employees based near Gusto offices in Denver, San Francisco, or New York City are expected to work in-office on designated days approximately two to three days per week or more depending on the role. Approved work from other locations requires secure, reliable, consistent internet access. The company also emphasizes regular and predictable attendance for in-office, hybrid, and fully remote employees.

Requirements

8–10+ years of product design experience.
At least 3 years of experience leading and managing design teams.
Experience designing in complex domains such as financial products, healthcare, or similarly regulated environments.
Experience setting UX direction across multiple teams and influencing product strategy.
Ability to drive alignment across cross-functional partners and represent design in high-stakes strategic conversations.
Strong systems thinking and a track record of turning interconnected, complex workflows into simple, intuitive experiences.
Clear, direct communication and storytelling skills, including 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.

Nice To Haves

Ability to assess AI-generated design directions, determine when to use or override them, and raise the quality bar on AI outputs.
Experience leading product initiatives where AI or automation is central to the user experience, including representing uncertainty, surfacing errors gracefully, and preserving user agency when automation fails, particularly in high-stakes contexts.
Experience leading a team through an AI workflow transition, including changing team practices and establishing new norms and standards.

Responsibilities

Lead end-to-end design for Payroll, creating 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, Operations, and others to set strategy and roadmaps.
Lead product initiatives centered on AI and automation to simplify payroll and reduce manual work without compromising accuracy or trust.
Work with Research and Data to uncover customer insights and translate them into actionable UX priorities.
Influence product and technical roadmaps by advocating for design quality, customer needs, and long-term system health.
Set quality and judgment standards for design work, including AI-assisted work, and determine when outputs meet the bar or need improvement.
Define and scale shared patterns, principles, and standards that promote quality, consistency, and velocity.
Manage and grow a team of designers through mentorship, clear direction, and hands-on support.
Champion Payroll as the foundation of Gusto’s broader People Platform and ensure seamless integration across Benefits, Time & Attendance, and third-party tools.