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Principal Product Manager, Customer Onboarding

Gusto - San Francisco, CA, United States - In-office - posted 2026-07-30

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Gusto is a mission-driven HR and payroll platform serving over 500,000 small businesses. The Growth & Commerce team owns acquisition flows, cross-sell experiences, and revenue-generating platforms. You'll lead the customer onboarding product strategy, focusing on simplifying and clarifying Gusto's complex onboarding experience—particularly for payroll and expansion flows. In this role, you'll own onboarding conversion experiences end-to-end, with a specific focus on developing AI-powered solutions (including an AI agent) to guide customers through Gusto's multi-step setup process. Your north star is increasing conversion by reducing friction and complexity in onboarding. Day-to-day responsibilities include: defining and owning the onboarding product roadmap; collaborating tightly with core experiences, growth, payroll, employee onboarding, and tax registration teams; prototyping and shipping AI-native experiences; and using data and customer research to drive iteration. You'll work in a lean, empowered product organization where PMs move fast, wear multiple hats (design, prototype, ship), and leverage AI as a co-builder. Gusto values mission-driven builders who thrive in ambiguity, combine sharp product judgment with AI fluency, and care deeply about lifting up small business owners. The company has 2,700+ employees across the US, Canada, Mexico, and Turkey, with over $500M in annual revenue and strong market recognition (G2 #1 best software for small business, 2024). All full-time employees receive competitive base pay, benefits, and equity (RSUs). The role is based in San Francisco with teams also in Denver and New York.

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