Principal Product Manager, HR Experiences

About Gusto, Inc. Gusto has been growing the small business economy with technology and heart for more than a decade. Launched in 2012 as ZenPayroll, today Gusto serves more than 500,000 businesses nationwide. Each year we process tens of billions of dollars of payroll and provide employee benefits—like health insurance and 401(k) accounts—while helping companies create incredible work places. Through one refreshingly easy, integrated platform, we automate and simplify your payroll, benefits, and HR, all while providing expert support. You and your employees will get the peace of mind you need to do your best work. We offer: ▪️ Automated Tax Filing ▪️ Comprehensive HR & Benefits ▪️ Contractor Support ▪️ Integrations & Employee Self-Service ▪️ And so much more We started Gusto with a simple belief: small businesses are the backbone of the American economy. And they deserve a partner that is committed to making their life better.

Gusto, Inc.

Growing the small business economy with technology and heart 🧡⚡️

compliancepayrollhuman resourcesbenefitsand small business

G

gusto.com

1,001-5,000 employees

Software Development

San Francisco, California

2011

Privately Held

168k LinkedIn followers

Raised $746.1M

• 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)
• 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.
• 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.

• 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.
• 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.

• Competitive base pay
• Equity
• RSUs
• Health insurance
• 401(k)