Senior Product Manager, Gusto
Document Studio
$184-230k
+ RSUs
2-3 days a week in office
Automated payroll, benefits & HR platform
Open for applications
Automated payroll, benefits & HR platform
1001+ employees
Open for applications
$184-230k
+ RSUs
2-3 days a week in office
1001+ employees
Company mission
To grow the small business economy.
Role
Who you are
- 5+ years of product management experience. You have a track record of owning significant product areas and shipping outcomes in fast-moving environments. Ideally with additional experience in roles that involve helping people navigate choices they don't have the domain knowledge to make confidently
- AI product experience. You've shipped AI products where getting it wrong has real stakes — and you understand when AI adds value. You understand how to scope AI capabilities, manage uncertainty, and design for human-in-the-loop
- Strong product craft. You’ve shipped products that users love and that moved the needle. You’re rigorous about problem definition, scope, and success—and you know when to simplify or cut
- Platform and systems thinking. You identify the generalizable structure underneath multiple use cases and build toward it. Experience in any domain where structured logic needs to scale — compliance, legal, financial, medical, pricing, knowledge infrastructure — matters more here than document-specific background
- Cross-functional collaboration. You've collaborated with domain experts to shape product experiences and build always-on processes
- Technical fluency. You can have real conversations with engineers about AI systems, rules engines, and content infrastructure. You don't need to write code, but you need to understand what's possible, what's expensive, and where technical constraints shape what you can build
- If you don't think you meet all of the criteria above but still are interested in the job, please apply. Nobody checks every box, and we're looking for someone excited to join the team
What the job involves
- We’re looking for high-autonomy, entrepreneurial Product Managers to build high-impact solutions for small businesses and their employees. We believe in high-ownership Product Managers who operate like business owners — owning an entire roadmap end to end and shipping product all the way from strategy through to the nitty-gritty details (some describe this kind of role as a “GM” type role)
- Our Product team is lean, which means you’ll have a high degree of impact and ownership. We believe in smaller, empowered teams that move quickly with less overhead. You’ll move fast by pairing sharp product judgment with fluency in AI tools — automating what slows teams down and amplifying what makes them creative and high-performing
- We’re boundaryless builders. Lines between roles are intentionally blurred, and our PMs do whatever it takes to deliver outcomes. You’ll prototype, automate, design, and ship — using AI as your co-builder to turn problems into durable solutions that deliver customer value with urgency and care
- We’re here to serve small and medium businesses. Gusto has a strong mission-driven culture, and we care deeply about lifting up these business owners — building technology for an AI-first world that gives them the superpowers to run and grow their businesses with confidence
- We’re comfortable with change. Our environment moves fast, and PMs here thrive in ambiguity — blending curiosity, experimentation, and AI-native craft to shape how products (and work itself) are built at Gusto
- We have a clear vision for how AI-powered tools will transform HR for small businesses, and we're looking for a Senior Product Manager to make it real: sharpen priorities, own outcomes, and partner deeply with engineering and design to ship products that matter
- HR Labs powers our HR Partners service offering, Gusto's fastest-growing business line and where many of our boldest AI bets are happening
- Our goal is to deliver real human expertise at scale through AI-native tools and agentic workflows
- A team of HR professionals delivers expert, personalized guidance to our small business customers, and the platform you build is what makes that possible
- You'll own both the customer-facing and internal tools: partner workspaces, agentic workflows, AI-assisted document generation, and the bridge to future customer self-service
- The blend of internal and customer-facing products means you'll have unusual freedom to experiment and iterate with real users (our HR Partners) before concepts graduate to broader release
- You'll be the product partner to a senior designer and a strong engineering team that includes founding engineers, UX prototypers, and product engineers who want to co-define what gets built, not just receive specs
- We need a PM who thrives in that environment: someone with strong product craft, real AI product experience, and the ability to push creative boundaries while executing quickly
- Own product strategy and roadmap for the HR Partners platform—refining and extending the existing vision, making hard prioritization calls, and ensuring we’re building the right things for partners and, over time, for customers
- Work side by side with engineering and design: clarify problems, frame opportunities, and shape solutions together rather than handing over finished specs. You’ll be a true partner, not a ticket-writer
- Drive discovery and validation with HR partners and other stakeholders—synthesize feedback, identify patterns, and turn insights into clear requirements and success criteria
- Define and track outcomes (usage, quality, efficiency, business impact) and use data to inform what we build next
- Operate in ambiguity: our roadmap is evolving, the AI landscape is moving fast, and the “right” product isn’t always obvious. You’ll help the team navigate that uncertainty with structure and judgment
- Think creatively about AI-native experiences, beyond chatbots and forms. The bar here is high: outputs need to be accurate (HR has real compliance stakes), tailored to each customer's situation, and genuinely useful rather than generic
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 co-founders of Gusto all come from small business backgrounds, which is why they created a platform 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 position in a competitive market, including the likes of Ardius, Symmetry and Guideline.
Through its continued acquisitions and fundraising efforts, the company has carved out a strong position for itself in the space. It continues to expand its platform, for example by partnering with Parafin to launch a payroll line of credit for small businesses, and more recently launching Cofounder, an AI teammate tailored to the needs of small businesses.
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
- 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
- Paid vacation, sick time, bereavement, and holidays, paid leaves, sabbatical, and more
- Free meals and refreshments at the office (conversation and community is an added bonus!)
Company HQ
Central Waterfront, San Francisco, CA
Leadership
Joshua Reeves
(CEO & Co-Founder)Studied Electrical Engineering at Stanford and went onto co-found Gusto in 2011.
Tomer London
(CPO & Co-Founder)Has a PhD in Electrical Engineering from Stanford. Was a Researcher at Intel, and then interned at Bump Technologies. Co-founded Vizmo before co-founding Gusto in 2011.
Edward Kim
(Head of Technology & Co-Founder)Studied Electrical Engineering at Stanford. Was Senior Project Engineer at Volkswagen of America Electronics Research Lab and then co-founded Picwing before co-founding Gusto in 2011.
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