Principal Product Manager, Customer Onboarding

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 Team:

The Growth & Commerce team is responsible for the shared surfaces and platforms that power Gusto’s growth & primary revenue generating experiences. This includes being responsible for the acquisition flows, cross-sell & pricing experiences, as well as the infrastructure that powers pricing, invoicing and revenue communications. The team is responsible for a meaningful portion of Gusto’s overall revenue goals, and has central, shared responsibility for driving traffic to Gusto’s wide range of small business products.

We are seeking a seasoned Product Manager with a creative mindset to drive growth through innovative customer onboarding strategies. This role involves developing an AI agent to escort the customer through Gusto’s complex onboarding experience. The ideal candidate will excel in creating AI experiences to help customers navigate the issues important to them.

Here’s what you’ll do day-to-day:

• Ownership: Own Gusto onboarding customer experiences related to driving conversion, especially experiences that assist customers navigate the complexities of Gusto payroll and expansion onboarding.
• North Star: Increase conversion of Gusto onboarding experience through experiences that simplify and clarify the overall and component specific onboarding process
• Collaborate: Tight collaboration will include the Gusto core experiences team, other growth teams and the various product teams associated with the onboarding - especially payroll, employee onboarding, state and federal tax registration

Here’s what we're looking for:

• 8+ years of Product Management experience with a proven track record of shipping successful products

• Hands-on experience building and launching AI-powered customer experiences

  • Vision for how AI can fundamentally transform digital experience design and user interaction paradigms

• Deep understanding of small business challenges, with the ability to identify, frame, and articulate SMB pain points effectively

• Demonstrated ability to craft compelling, action-oriented messaging that resonates with small business audiences

• Proven ability to work effectively across cross-functional teams including engineering, design, marketing, and sales

• Strong design partnership skills with the ability to collaborate with designers to push creative boundaries

• Excellent analytical and problem-solving capabilities with a data-informed approach to decision-making

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 $224,000/yr in Denver & most major metro locations, and $210,000/yr to $263,000/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.

Where do PMs at Gusto work?

We have offices in Denver, San Francisco, and New York and have remote team members across the US and Canada. We are actively hiring for this role in San Francisco. Our open roles will specify on the careers page and in the job description where the position is eligible for work.

(1) Business Applications with Planned Wages ( )

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.

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.

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