Senior Design Manager, Payroll at Gusto - Grow in Columbus

Headquarters: Denver, CO - Hybrid; New York, NY - Hybrid; San Francisco, CA - Hybrid; Toronto, Ontario - Remote

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.

All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.

AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

About Design at Gusto

Design at Gusto is made up of over 80 creative, collaborative people who care deeply about our mission to empower small businesses and their employees. We're a cross-functional group that is always looking for opportunities to build understanding and empathy for the people who use Gusto. We don't care much about swim lanes and though we care deeply about quality and craft, we are never precious about it. We work closely with cross-functional partners in Product, Engineering, Data, and Marketing to design, build, and ship experiences that make a real difference. We believe great design can make hard things possible, even delightful.

We are building an AI-native design organization — and we mean that seriously. We're looking for designers who are already working this way: using AI to prototype ideas quickly, shorten customer feedback loops, and ship quality UX directly to customers. This isn't a future aspiration — it's how we work now, and it's changing what the design role looks like at Gusto and across the industry.

About the Role

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, reciprocal 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, set the quality and judgment standard for AI-assisted design work across the broader Design team, and contribute to platform standards that help others across Gusto build consistent, high-quality experiences.

About the Team

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.

Here's what you'll do day-to-day:

• 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.

Here's what we're looking for:

• 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.

Ideally you have:

• 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.

At Gusto, we strive to provide rewards that empower employees to achieve their financial and personal goals. We offer competitive compensation packages with a strong emphasis on equity based compensation (ownership in Gusto). To learn more about Gusto's compensation philosophy and benefits offerings please view our Total Rewards Approach page.

Our cash compensation range for this role is $172,000/yr to $237,000/yr in Denver & most remote locations, and $202,000/yr to $279,000/yr in San Francisco, Seattle & New York. Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above.

At Gusto, we don't use titles the traditional way, as a signal of rank or hierarchy. Instead, our titles describe two things at once — your craft (what you do, e.g. Engineering, Design) and your scope of ownership (what you're accountable for) — which is why you'll see something like "Head of X" instead of a rank word like "Director" that tells you neither. Because of this, the title on this posting may look different from what you'd expect based on the scope and seniority of the role, and from how similar roles are typically titled elsewhere. If you have questions about how this role compares to your current title or level, your recruiter can help translate.

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.

When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.

Reliable, consistent presence: We expect regular and predictable attendance, whether you're working in-office, hybrid, or fully remote, so that you stay closely connected to your team, customers, and stakeholders in real time and ensure colleagues and customers receive the timely support and responsiveness they deserve.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.

Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.

Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

To apply: https://weworkremotely.com/remote-jobs/gusto-inc-senior-product-design-manager-payroll