Senior Staff Product Designer, Gusto
Benefits
$172-253k
Actual salary range is dependent on location
Automated payroll, benefits & HR platform
Be an early applicant
Automated payroll, benefits & HR platform
1001+ employees
Be an early applicant
$172-253k
Actual salary range is dependent on location
1001+ employees
Company mission
To grow the small business economy.
Role
Who you are
- If you’re passionate about crafting the next era of product design and helping small businesses harness the power of AI, come join us
- 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
What the job involves
- 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, with a focus on the role AI will play to connect 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 (what the system does), human-in-the-loop moments (what experts do), and clear decision policies for when to automate, escalate, or pause
- Your work should measurably reduce customer effort, increase accuracy and compliance, and bend cost-to-serve down while keeping the experience warm and trustworthy
- 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
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.
Steph
Company Specialist at Welcome to the Jungle
Insights
45% employee growth in 12 months
Company
Funding (last 2 of 9 rounds)
May 2022
$55m
SERIES E
Aug 2021
$175m
SERIES E
Total funding: $706.3m
Company benefits
- Health and Wellbeing: Medical, dental, and vision insurance for employees and dependents. Family care and support, including family planning and fertility benefits. Gender-affirming care and support. A variety of mental health resources.
- Time Away: It's important to take time away for yourself or to take care of your family. Gusto offers paid vacation, sick time, bereavement, and holidays, paid leaves, sabbatical, and more!
- Free meals and refreshments: If you work at one of our offices, enjoy food, drinks, and snacks— on us. Conversation and community is an added bonus!
- Perks:
Company HQ
Central Waterfront, San Francisco, CA
Leadership
Joshua Reeves
(Co-Founder & CEO)Studied Electrical Engineering at Stanford and went onto co-found Gusto in 2011.
Tomer London
(Co-Founder & CPO)Has a PhD in Electrical Engineering from Stanford. Was a Researcher at Intel, and then interned at Bump Technologies. Co-founded Vizmo, a mobile self-service technologies company, in 2008. Co-founded Gusto in 2011.
Edward Kim
(Co-Founder & Head of Engineering)Studied Electrical Engineering at Stanford. Was Senior Project Engineer at Volkswagen of America Electronics Research Lab and then co-founded Picwing, a printed photos company, in 2008. Co-founded Gusto in 2011.
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