Senior Product Design Manager (Payroll) Gusto
Automated payroll, benefits & HR platform for small businesses.
Permanent
Denver, New York, San Francisco, Toronto
A few days home
172K to 279K $ a year
> 5 years
Communication skills
Payroll
Mentoring
Foundation
You'll be part of
Denver, New York, San Francisco, Toronto
3794 employees
Finance
Our take
For many small businesses, vital administrative tasks such as payroll, taxes, and benefits are manual tasks that take time and energy which many SMB owners don’t have. The three co-founders of Gusto – all coming from small business backgrounds – collaborated on a Fintech company that would handle employee payments, benefits administration, and compliance support specifically for small businesses. The company may have started slowly, as the founders focused on nailing each individual aspect of Gusto’s operations, but has now skyrocketed to unicorn status with more than 400,000 customers and a multi-billion dollar valuation. And in 2021, Gusto began acquiring other companies to strengthen its offering and its position in a competitive market, including two other fintech startups, Ardius and Symmetry. Through its continued acquisitions and fundraising efforts, the company has carved out a strong position for itself in the space. Although Gusto has found itself impacted by the macroeconomic situation, through the significant effect it has had on its clientele, the company still appears positive for the future after raising funds in 2023 that has seen it reach key profitability benchmarks. It continues to expand its platform, most recently partnering with Parafin to launch a payroll line of credit for small businesses. With a growing suite of services and a clear focus on supporting small businesses through changing economic conditions, Gusto looks set to sustain its momentum and further strengthen its position in the HR and payroll technology market.
You'll be working on
- For the hundreds of thousands of small businesses we serve, our mission starts with one of their most critical responsibilities: paying their team. Getting payroll right isn’t just a feature—it’s the foundation of trust with every business that relies on us
- As the Product Design Manager for Payroll, you’ll lead design in this senior level position for one of Gusto’s most complex and consequential product areas, shaping the future of a product that millions of people rely on for financial stability and personal prosperity
- This is a high-impact, high-visibility role with broad scope. You’ll manage a team of designers and set the UX direction for Payroll, partnering closely with Product, Engineering, Research, Data, Ops, Compliance, and others to take on payroll complexity so our customers don’t have to
- Your work will include simplifying complex, interconnected workflows, defining a long-term UX vision and rallying others around it, and leading automation and AI initiatives that make the work of paying a team disappear. You’ll also mentor designers, raise the bar for craft across the broader Design team, and contribute to platform standards that help others across Gusto build consistent, high-quality experiences
- Payroll is the foundation of Gusto and our most-used, most-loved product. It’s the first Gusto experience many customers interact with, and it continues to power their success as they grow. Payroll also underpins our broader ecosystem, enabling the adoption of Benefits, Time Tracking, HR tools, and so much more
- Our team is tasked with evolving and scaling this core experience for small businesses of all sizes, from solo entrepreneurs to growing companies. We focus on taking on the complexity of payroll so our customers don’t have to—making payroll faster, more flexible, and increasingly hands off
- Lead end-to-end design for Payroll, shaping experiences that help small businesses pay their teams properly, 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 AI and automation initiatives that simplify payroll and reduce 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
Benefits
- Gender-affirming care and support
- Family care and support, including family planning and fertility benefits
- A variety of mental health resources
- Medical, dental, and vision insurance for employees and dependents
- Free meals and refreshments at the office (conversation and community is an added bonus!)
- Paid vacation, sick time, bereavement, and holidays, paid leaves, sabbatical, and more
We're looking for
- A genuine bond to Gusto’s mission and the needs of small businesses
- Deep systems thinking, with a track record of turning interconnected, complex workflows into experiences that feel simple and intuitive
- 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
- 8–10+ years of product design experience, with at least 3 years leading and managing design teams
- Experience setting UX direction across multiple teams and influencing product strategy — not just executing on it
- 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
- Clear, direct communication and storytelling skills, with the ability to explain design decisions and influence partners at all levels
- Proven ability to drive alignment across cross-functional partners and represent design in high-stakes, strategic conversations
- 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
- Experience designing in complex domains i.e. financial products, healthcare, or similarly regulated environments