Gusto
Senior Staff Product Designer, Benefits
At Gusto, we’re on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers.
About The Role We’re hiring a Senior Staff Product Designer to define, ship, and scale a new Benefits product area. In this role, you’ll design the software to service experience, focusing on AI’s role in connecting the digital experience, support, sales, and operations teams while maintaining the warmth and clarity customers expect from Gusto.
You’ll operate at two altitudes: set the north star vision for an emerging area, then drive an MVP and fast iterations that prove value, de‑risk, and lay the groundwork for rapid scale. You’ll collaborate with Product, Engineering, and Data to design agentic workflows, human‑in‑the‑loop moments, and clear decision policies for when to automate, elevate, or pause.
Here’s What You’ll Do Day‑to‑Day
Chart the path forward: Drive 0→1 strategy for a new product area, creating a north star that shows how humans and AI collaborate to deliver accurate, empathetic, and scalable experiences for small businesses.
Design experiences that empower: Define first‑principles approach to help teams decide when automation should act, when people should lead, and how systems learn over time.
Bridge software and service: Partner with CX and Operations to design a human + AI service model where AI is the connective tissue that streamlines workflows, reduces cognitive load, and prepares the system for rapid scale.
Partner to make it real: Work across Gusto to collaborate with Product, Engineering, and Data to define and execute your strategic vision. Build systems and rituals to prototype, evaluate, and safely scale AI capabilities.
Elevate the bar: Work fluently with AI as a design material. Shape design systems and evaluation patterns that raise both the craft and ethics of intelligent experience design across the company.
Measure what matters: Design for observability and feedback so every model decision can be measured, adjusted, and improved through real‑world signals.
What We’re Looking For
10+ years of product design experience, with a proven track record of leading at the product or portfolio level, including multiple 0‑to‑1 launches that scaled.
Builder mindset: Hands‑on craft paired with strong product sense. You’ve shipped ambitious ideas, influenced strategy, and driven alignment through design.
Comfort with complexity: Experience creating simple, guided experiences in domains that are regulated, multi‑actor, or technically dense.
Service‑design fluency: Experienced in crafting end‑to‑end journeys where software, people, and policy work together. You see CX and Ops as co‑designers, not downstream recipients.
AI as design material: You’ve designed AI‑assisted or AI‑powered experiences that simplify workflows, guide decision‑making, or enhance human judgment. You understand how to shape prompts, evaluate outcomes, and design for transparency, safety, and trust.
Strategic acumen: Ability to contribute directly to business and product strategy, influence executive stakeholders, and connect design outcomes to measurable impact.
High‑quality bar: Advocate for design craft and accessibility while delivering iteratively; you balance speed with raising the bar.
Collaborative leadership: Known for mentoring senior ICs, shaping org‑wide opinions, and creating leverage across teams.
Passion for Gusto’s mission: Deep empathy for small businesses and a belief in the power of benefits to transform lives.
Compensation & Benefits Our cash compensation range for this role is $172,000/yr to $215,000/yr in Denver & most remote locations, and $202,000/yr to $253,000/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.
We offer competitive compensation packages with a strong emphasis on equity‑based compensation (ownership in Gusto). For more details, please view our Total Rewards Approach page.
Work Location & Remote Policy Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees based in those locations are expected to work from the office on designated days approximately 2‑3 days per week (or more depending on role). This expectation also applies to Gusto’s subsidiary, Symmetry, whose office is in Scottsdale.
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.
Equal Opportunity Employer Gusto is a proud 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. We consider qualified applicants with criminal histories, consistent with applicable federal, state and local law, and are committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our application procedures.
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About The Role We’re hiring a Senior Staff Product Designer to define, ship, and scale a new Benefits product area. In this role, you’ll design the software to service experience, focusing on AI’s role in connecting the digital experience, support, sales, and operations teams while maintaining the warmth and clarity customers expect from Gusto.
You’ll operate at two altitudes: set the north star vision for an emerging area, then drive an MVP and fast iterations that prove value, de‑risk, and lay the groundwork for rapid scale. You’ll collaborate with Product, Engineering, and Data to design agentic workflows, human‑in‑the‑loop moments, and clear decision policies for when to automate, elevate, or pause.
Here’s What You’ll Do Day‑to‑Day
Chart the path forward: Drive 0→1 strategy for a new product area, creating a north star that shows how humans and AI collaborate to deliver accurate, empathetic, and scalable experiences for small businesses.
Design experiences that empower: Define first‑principles approach to help teams decide when automation should act, when people should lead, and how systems learn over time.
Bridge software and service: Partner with CX and Operations to design a human + AI service model where AI is the connective tissue that streamlines workflows, reduces cognitive load, and prepares the system for rapid scale.
Partner to make it real: Work across Gusto to collaborate with Product, Engineering, and Data to define and execute your strategic vision. Build systems and rituals to prototype, evaluate, and safely scale AI capabilities.
Elevate the bar: Work fluently with AI as a design material. Shape design systems and evaluation patterns that raise both the craft and ethics of intelligent experience design across the company.
Measure what matters: Design for observability and feedback so every model decision can be measured, adjusted, and improved through real‑world signals.
What We’re Looking For
10+ years of product design experience, with a proven track record of leading at the product or portfolio level, including multiple 0‑to‑1 launches that scaled.
Builder mindset: Hands‑on craft paired with strong product sense. You’ve shipped ambitious ideas, influenced strategy, and driven alignment through design.
Comfort with complexity: Experience creating simple, guided experiences in domains that are regulated, multi‑actor, or technically dense.
Service‑design fluency: Experienced in crafting end‑to‑end journeys where software, people, and policy work together. You see CX and Ops as co‑designers, not downstream recipients.
AI as design material: You’ve designed AI‑assisted or AI‑powered experiences that simplify workflows, guide decision‑making, or enhance human judgment. You understand how to shape prompts, evaluate outcomes, and design for transparency, safety, and trust.
Strategic acumen: Ability to contribute directly to business and product strategy, influence executive stakeholders, and connect design outcomes to measurable impact.
High‑quality bar: Advocate for design craft and accessibility while delivering iteratively; you balance speed with raising the bar.
Collaborative leadership: Known for mentoring senior ICs, shaping org‑wide opinions, and creating leverage across teams.
Passion for Gusto’s mission: Deep empathy for small businesses and a belief in the power of benefits to transform lives.
Compensation & Benefits Our cash compensation range for this role is $172,000/yr to $215,000/yr in Denver & most remote locations, and $202,000/yr to $253,000/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.
We offer competitive compensation packages with a strong emphasis on equity‑based compensation (ownership in Gusto). For more details, please view our Total Rewards Approach page.
Work Location & Remote Policy Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees based in those locations are expected to work from the office on designated days approximately 2‑3 days per week (or more depending on role). This expectation also applies to Gusto’s subsidiary, Symmetry, whose office is in Scottsdale.
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.
Equal Opportunity Employer Gusto is a proud 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. We consider qualified applicants with criminal histories, consistent with applicable federal, state and local law, and are committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our application procedures.
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