Head of Product, New Customer Experience

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: • 500,000+ small businesses served nationwide • Named #1 best software for small business by G2 • 2,700+ employees in the United States, Canada, and Mexico, and growing • Over $1B 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 Role: Gusto is looking for an experienced Product leader for our New Customer Experience team. Gusto is known as the trusted payroll solution for hundreds of thousands of SMBs. As we expand as the trusted small business partner with new multi-product offerings, we need to ensure new customers can clearly see, and choose, the Gusto that’s right for their business. As Head of Product, New Customer Experience, you will be responsible for the entire product experience a small business takes from potentially never having heard of Gusto, to activating the Gusto products that help them start, run, and grow. Every new Gusto customer comes through the surfaces your team owns, which makes this one of the highest-leverage product roles at the company. About the Team: New Customer Experience is part of Gusto's Growth organization and covers four areas: our top-of-funnel web experience, onboarding, activation, and the shared onboarding platform that other Gusto product teams build on. You will lead a team of product managers and partner daily with Engineering, Design, Data, Marketing, Sales, and Finance. Onboarding is genuinely hard for SMBs: tax IDs, bank verification, signatories, prior payroll history. Our job is to make that feel less like paperwork and more like being guided through it by a small business expert. Here’s what you’ll do day-to-day: • 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. • 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. • 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. • Empowerment: Directly coach and lead a talented team of senior product managers. You will raise the bar on craft, customer understanding, and execution velocity. Here’s what we're looking for: • 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 instin