Head of Product, New Customer Experience

gusto· 35 open roles

Location TBD On-siteFull-timeYesterday

Salary

Undisclosed

Experience

Mid

Job Type

Full-time

Posted

Yesterday

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About This RoleAI processing…

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.

Key Responsibilities

1
Ownership: You will own the end-to-end new customer experience, including determining the best way to natively include AI throughout to assist customers. Set and evangelize a strategy for how small businesses discover, evaluate, and start using Gusto, including how we show up in AI assistants and agentic surfaces, where a prospective customer may never visit our website at all.
2
North Star: Create a best-in-class new customer experience which grows the number of small businesses who choose Gusto and get successfully set up - increasing acquisition volume, optimizing onboarding conversion, and establishing Gusto as the default small business partner solution.
3
Collaborate: You'll work closely with every function: Engineering, Design, Data, Marketing, Sales, and Finance to bring your vision to life. You’ll rally cross-functional teams and leaders around a shared onboarding platform strategy.
4
Empowerment: Directly coach and lead a talented team of senior product managers. You will raise the bar on craft, customer understanding, and execution velocity.

Requirements

10+ years of direct Product Management experience, including 4+ years leading and managing product managers.
A track record owning a growth, acquisition, or onboarding funnel with direct accountability for a conversion or revenue number, not just shipping features. You know your funnel numbers cold.
Hands-on experience shipping AI-powered customer experiences. You have a real point of view on what acquisition looks like when the front door is an AI assistant rather than a website, you know how to evaluate whether an AI experience actually beats the flow it replaced, and you treat latency and cost as product constraints. You use AI in your own work to research, synthesize, and prototype.
Experience in selling to SMBs, and experience in a multi-product company with shared platforms and real cross-team dependencies
Experience owning a public web surface (e.g. marketing site, CMS) a plus.
Strong experimentation instincts and the judgment to know when a flat result means iterate and when it means stop. You are a builder who stays close to the work
Experience partnering closely with Marketing, Sales, and Finance, with direct accountability to a revenue target or P&L

Perks & Benefits

We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers.

All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success.