Senior Product Manager, Document Studio

About the role

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.

By the Numbers:

• Named #1 best software for small business of 2024 by G2
• 2,700+ employees in the United States, Canada, Mexico, and Turkey and growing
• Over $500M in annual revenue
• The SMB market is large (and growing!) with huge opportunities for Gusto to make an incredible impact for SMBs
• There are 6.2M employers in the US, 98% have fewer than 100 employees (1)
• 550,000 new businesses are created each year in the US (1)

What Product Management is like at Gusto

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.

About the Team

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.

Document Studio is one of our most ambitious product bets: an experience that helps small business owners navigate the hard HR decisions, a new hire, a compensation change, a difficult termination, and generates the right documentation, personalized to their situation, compliant with their state, reflecting how they want their culture and values to come through, backed by rules they can trust.

The foundation is in early stages: a Handbook product is in beta, and the internal platform is an MVP. Our ambition is considerably bigger than what's been built. The customer experience is still evolving: what it looks and feels like to be guided through a termination, a comp change, or a new hire without needing to be an HR expert. The scale is real: employment law varies across all 50 states, and the content pipeline has to handle that without becoming a bottleneck. And the internal engine, the rules and content infrastructure that makes trusted output possible, is still being defined. This is one of Gusto's most ambitious bets, and the person who takes this role will shape it.

Here’s what you’ll do day-to-day

• Own product strategy and roadmap for the Document Studio platform—Defining the vision, making hard prioritization calls, and ensuring we’re building the right things 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 customers and our internal experts—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.

Here’s what we're looking for

• 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.