Senior Staff Engineer, Expansion Experiences

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. Most small businesses on Gusto are only using a fraction of what could actually help them run their business: the right plan tier, the right benefit, the right feature at the right moment. We're investing in building more of that expertise directly into the product itself, through recommendations, nurture journeys, and self-serve conversion paths that work alongside the support our Sales team already provides. As a Senior Staff Software Engineer on Expansion Experiences, you'll own outcomes across that whole funnel, from the moment a customer's need surfaces through to the ongoing value of what they adopt. That means real autonomy: shaping the technical approach, partnering with Product, Design, and Data Science to decide what's worth building, calling the shots on what to test now versus later, and flagging the technical investments the team will need before they become urgent. If you want your work to move retained and expansion revenue for a company serving 500,000+ small businesses, this is the team. Here's what you'll do day-to-day: • Own outcomes across the full expansion funnel, not just a single surface or feature within it. • Shape the technical approach and architecture behind recommendations and conversion journeys so it holds up as a foundation other initiatives can build on. • Make sharp scoping calls under a time box: ship the simplest version that proves or disproves an idea, then iterate based on what you learn. • Design experiments and use ambiguous or noisy data to decide what's worth scaling versus cutting. • Partner independently with Product, Design, and Data Science to help shape the roadmap, not just execute it. • Raise the engineering bar through pragmatic technical direction, strong code review, and mentoring engineers around you, scoping out work and delegating it to other engineers on the team once it's ready to hand off. Here's what we're looking for: • Successful applicants typically have 10+ years of software development experience, including building and shipping full-stack, customer-facing products at scale. • A product-minded engineer who starts from the customer problem and the metric that matters, not just the ticket, and can operate independently across product, design, and data partners. • Experience in a growth, lifecycle, or conversion-focused context (onboarding, upsell flows, personalization, or recommendations) is ideal — or a demonstrated ability to think this way even without the exact domain background. • Demonstrated ability to move quickly and execute with high quality — someone who ships, measures, and iterates rather than waiting for perfect certainty. • Experience owning multi-quarter initiatives end to end, from early concept through measurable business impact. • Comfort navigating ambiguity and leading peers through influence, without relying on formal authorit