Principal Product Manager, AI Assistant

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. By the Numbers: • Named #1 best software for small business of 2024 by G2 • 2,700+ employees in the United States, Canada, Mexico, and Turkiye 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: • 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 CoreX AI team: CoreX AI builds and powers AI experiences that make Gusto the best teammate for small businesses. Our largest AI bets embed directly in small business workflows whether that's answering a quick question or handling the task itself. Our customers trust us with their payroll, their employees' benefits, and their money decisions where mistakes have real, immediate consequences. We give small businesses trusted and powerful AI tools that supercharge how they work. We're at an inflection point across everything we own, and we're looking for a product leader ready to accelerate our AI bets as we build toward that future. This is a role for builders who can work across Gusto, reason about API design and model behavior as comfortably as customer experience, and bring hands-on experience building with AI. About the Role: You'll define how Gusto's conversational assistant works, behaves, and earns customer trust and how small businesses use it to get real work done across payroll, benefits, HR, and beyond. • Develop a deep understanding of how small businesses actually work inside Gusto today the workflows they run, where they get stuck, and the work they'd hand off if they could • Lead the product vision for Gusto’s conversational assistant that gives small businesses superpowers, and turn it into a coherent strategy a sharp perspective on where the assistant earns real value, and what we build first • Expand what the assistant can actually do. You'll partner with domain teams to grow tool and domain coverage across payroll, time, benefits, and compliance, and hold the bar on quality as coverage grows measured in real actions customers complete, not conversations they have • Define how we show up in our customers’ ecosystem and the surfaces where work naturally happens third-party connectors, messaging channels, and AI clients and decide what earns priority against the depth we have in the app • Partner with engineering and data teams on technical trade-offs: how we expose Gusto's capabilities to agents through our API and MCP layer, how the assistant embeds into our first-party surfaces, and where we take on debt to move faster • Partner with design and UXR to understand how customers actually feel about AI acting on their behalf, and use that to shape how we build • Move fast. Speed is our top priority, and you'll set a pace that reflects it shipping narrow slices that get customers value early rather than waiting on the complete build Here’s what we're looking for: • 10+ years building as a product manager, with experience owning meaningful scope and driving broad product or platform-level decisions • You're comfortable in a high-visibility role engaging directly with Gusto leadership and product leaders across the company, and driving decisions that stick • You believe in what AI can do for small businesses, and you're excited to build it. • You understand what it takes to build trusted AI products: writing evals, holding a real point of view on AI quality, and assuming the responsibility of a product customers rely on day-to-day • You're hands-on and you'd rather build than delegate — and you thrive in a culture that expects it • You’re comfortable spanning both platform thinking and UX/experience judgment within the same role • You develop sharp perspectives on the systems AI products need — RAG, ontology, and a scalable API strategy for agent-accessible systems • You’re comfortable with a fluid, expanding charter. This isn't a role with a static roadmap, given how fast AI development and the competitive landscape are moving. Our cash compensation amount for this role is $179,000/yr to $220,000/yr in Denver & most major metro locations, and $210,000/yr to $260,000/yr for San Francisco, Seattle & New York. Final offer amounts are determined by multiple factors, including candidate location, 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. 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