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—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy . 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, fra ... (truncated, view full listing at source)