Retirement AI Senior Staff Engineer

<div class="content-intro"><p style="line-height: 1.2;"> </p> <hr> <p><strong>About Gusto</strong></p> <p><span style="font-weight: 400;">At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our </span><a href="https://gusto.com/about/careers/total-rewards"><span style="font-weight: 400;">Total Rewards philosophy</span></a><span style="font-weight: 400;">. </span></p></div><p><strong>About the Role:</strong></p> <p>You’ll be a key engineer helping us ship real, user-facing AI at Gusto Retirement. This role is all about bias to action: owning problems end-to-end, getting working software in front of customers, and iterating quickly. You’ll work closely with a small, senior team to implement language-model-powered experiences. If you like being hands-on, making pragmatic technical decisions, working closely with product & design partners, and turning ideas into production features, you’ll be a great fit.</p> <p> </p> <p><strong>About the Team:</strong></p> <p>We’re a small, focused AI product team building practical, high-impact experiences to help people save for retirement at Gusto Retirement. The team is senior, collaborative, and very execution-focused—PMs bring strong ideas, and we own the execution fully. We work closely with product, design, and partner engineering teams, but keep tight ownership of our priorities and roadmap.</p> <p> </p> <p><strong>Here’s what you’ll do day-to-day:</strong></p> <ul> <li>Design, build, and ship production features that use large language models to solve real customer problems.</li> <li>Implement and integrate LLMs (prompting, tool loops, evaluation, monitoring, etc).</li> <li>Make pragmatic architecture decisions, de-risk tricky areas, and keep the work unblocked.</li> <li>Partner with product and design to refine ideas, shape scope, and iterate quickly on end-to-end experiences.</li> <li>Collaborate with other engineering teams to integrate with existing systems and unblock dependencies.</li> <li>Write clear, reliable, well-tested code that ships quickly and scales well.</li> </ul> <p> </p> <p><strong>Here’s what we're looking for:</strong></p> <ul> <li>10+ years of software engineering experience building and shipping production products or platforms</li> <li>Hands-on experience implementing LLM-powered features (e.g., RAG flows, agents, tool loops, workflow automation with language models, etc)</li> <li>Strong engineering skills (e.g., services, APIs, data flows); comfortable spending most of your time coding.</li> <li>Experience running or heavily contributing to a team’s execution: sprints, Jira, scoping, and cross-functional coordination.</li> <li>Bias to action: you default to trying things, iterating, and learning, rather than getting stuck in analysis or waiting for direction.</li> <li>Clear communicator who can work well with product, design, and other engineering teams without needing a formal management title.</li> <li>Experienced with Ruby on Rails (or any comparable language), React (or any comparable library).</li> </ul> <p><strong>Please no ... (truncated, view full listing at source)