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Head of Product, New Customer Experience

Gusto - San Francisco, CA, USA - Hybrid - posted 2026-09-18

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Salary: USD 243,000 - 292,000 / annual

Gusto is seeking an experienced Product leader to head the New Customer Experience team. This is a high-leverage role responsible for the entire product journey from awareness through activation—every new Gusto customer passes through surfaces owned by this team. Gusto serves 500,000+ small businesses with payroll, health insurance, 401(k)s, and HR solutions. The company has $1B+ in annual revenue and is expanding its multi-product offerings, requiring a best-in-class new customer experience that helps SMBs discover, evaluate, and successfully onboard onto Gusto. The New Customer Experience team is part of Gusto's Growth organization and covers four areas: top-of-funnel web experience, onboarding, activation, and a shared onboarding platform. You will lead a team of product managers and partner daily with Engineering, Design, Data, Marketing, Sales, and Finance. Day-to-day responsibilities include: - Owning the end-to-end new customer experience, determining how to natively integrate AI throughout to assist customers - Setting strategy for how small businesses discover, evaluate, and start using Gusto, including presence in AI assistants and agentic surfaces - Creating a best-in-class experience that grows acquisition volume, optimizes onboarding conversion, and establishes Gusto as the default SMB partner - Collaborating across all functions to bring vision to life and rally teams around a shared onboarding platform strategy - Directly coaching and leading a talented team of senior product managers, raising the bar on craft, customer understanding, and execution velocity Gusto's product culture emphasizes lean, empowered teams that move quickly; boundaryless builders who do whatever it takes to deliver outcomes; and comfort with change and ambiguity. AI is fundamental to how work gets done—all team members are expected to actively engage with AI tools relevant to their role. The company has physical offices in Denver, San Francisco, and New York City. Hybrid employees in these locations are expected to work from the office 2-3 days per week (or more depending on role). REQUIREMENTS: - 10+ years of direct Product Management experience, including 4+ years leading and managing product managers - Track record owning a growth, acquisition, or onboarding funnel with direct accountability for conversion or revenue metrics; must know funnel numbers cold - Hands-on experience shipping AI-powered customer experiences; real point of view on acquisition when the front door is an AI assistant rather than a website; ability to evaluate whether AI experiences beat replaced flows; treats latency and cost as product constraints; uses AI in own work for research, synthesis, and prototyping - Experience selling to SMBs and working in multi-product companies with shared platforms and cross-team dependencies - Experience owning a public web surface (e.g., marketing site, CMS) is a plus - Strong experimentation instincts and judgment to know when to iterate vs. stop; builder who stays close to the work - Experience partnering closely with Marketing, Sales, and Finance with direct accountability to revenue target or P&L

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