Principal Product Manager - HR Experiences

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 Team:

HR Experiences (HRX) builds the products that help small businesses hire, onboard, develop, and stay compliant: hiring and I-9s, performance, handbooks, training, labor law posters, and the tools our HR Partners use to serve their clients. Most of our customers are a department of one, an owner or office manager making consequential people decisions with no HR team to check their work.

Today we serve those customers mostly through software built in the GUI era: prescribed workflows and screens that customers have to learn, with human HR experts and advisory experiences for a growing set of them. For a meaningful segment, learning our workflows is not a must-have, and a GUI can never cover the long tail of needs that hundreds of thousands of businesses have. The opportunity ahead of us is to rebuild how HR gets delivered so that the product does the work and carries the judgment of an expert, and to make it AI-native from the start rather than a chat box bolted onto a GUI.

As Principal Product Manager, you'll be a senior individual contributor who owns the People Page experience and sets the experience direction for the HR Suite. You'll also own Training, which is where you'll build and learn quickly. You'll work hand in hand with the PM who owns the other verticals (Hiring, Onboarding, and Performance).

Here’s what you’ll do day-to-day:

• Ownership: You will own the People Page experience and how it evolves: new entry points, interactive patterns, and the experience principles that apply to every vertical in the HR Suite (hiring, onboarding, performance, and training). Today those verticals are built as prescribed workflows, and the team is bringing them to market parity. Working with the PM who owns each vertical, you'll shape what they become when the product does the work for the customer, whether that is conversational, embedded, agentic, or something else entirely, and where a GUI still earns its place. Changes to Hiring, Onboarding, and Performance happen in partnership with the PM who owns them, once each vertical meets its parity floor, and verticals adopt your principles at a pace that PM sets. You'll also own the Training vertical end to end, using it to build, ship, and learn quickly before those patterns spread to the rest of the suite.
• 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.

Here’s what we're looking for:

• 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.

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.

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.