Principal Product Manager, HR Experiences

Required

• North Star: Move Gusto from the GUI era to an AI-native one. Our 550K businesses have needs that differ by state, size, industry, and risk tolerance, and we can't build a separate solution for each. Your goal is to deliver far more value across that long tail, so each customer gets what they specifically need: their context imported, a confident and compliant recommendation instead of a menu of options, and the work done for them. You'll prove it by moving adoption and outcomes, not feature counts.
• Collaborate: You'll work closely with design, engineering, data, compliance, legal, product marketing, the PM who owns hiring, onboarding, and performance and the actions behind them, and our advisory teams (HR Partners and Ask an Expert), whose work shows where customers need judgment the product doesn't give today, to deliver outcomes no single team owns. Time with SMB HR operators is a regular part of the job.
• Build, not just specify. Prototype with AI tools, work with engineering to take prototypes to production, instrument what matters, and iterate on what customers do. The goal is to build beyond today's GUIs once each vertical is at baseline, not to re-skin them. Conversation is one pattern among several, so you'll design the interactive patterns that fit each job. Where a conversational, embedded, or agentic model delivers more value than a prescribed workflow, you'll make that case and ship it.
• Shape how the HR Suite shows up where customers already work, including Claude, ChatGPT, and other assistants, through MCP and integrations, in partnership with the PM who owns the action catalog, so a customer asking an AI assistant an HR question gets an answer grounded in their own Gusto data and can act on it without leaving the conversation.
• 8+ years of direct Product Management experience, with a track record of owning a significant product surface end-to-end and shipping products that moved the business.
• Real HR domain experience. You've lived these problems as a People/HR leader or founder who made these decisions firsthand, or you've built products in the HR, people, or compliance space. You know how an SMB HR operator thinks.
• Fluency in AI product patterns: conversational and agentic interfaces, interaction patterns beyond chat, LLM capabilities and limits, and how to design experiences people can trust. You've shipped products where AI does the work rather than guiding a user through a workflow, or you're clearly hungry to. You build working prototypes yourself rather than waiting for a handoff.
• A strong, opinionated point of view on where HR software is heading, and the judgment to tell a big swing from a distraction. You can set multi-year direction and still work through the details of a shipping feature, and you're comfortable getting a product to a competitive baseline first and building toward something bigger from there.
• Comfort with ambiguity and complexity, especially where the hard problem is experience design and product formulation, and where compliance, privacy, and multi-tenant trust are design constraints to solve.
• Exceptional written and verbal communication. You can make a sharp argument, rally a team around a direction, and bring skeptical stakeholders along.
• A bias for customer truth over internal opinion, and the discipline to validate with real users.
• Bonus: experience in HR, compliance, fintech, or another high-trust regulated domain; experience reimagining a mature, workflow-heavy product for AI, or converting an expert services motion into scaled software.