Staff Software Engineer, Retirement AI

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.

About the Team:

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.

Here’s what you’ll do day-to-day:

• Design, build, and ship production features that use large language models to solve real customer problems.
• Implement and integrate LLMs (prompting, tool loops, evaluation, monitoring, etc).
• Make pragmatic architecture decisions, de-risk tricky areas, and keep the work unblocked.
• Partner with product and design to refine ideas, shape scope, and iterate quickly on end-to-end experiences.
• Collaborate with other engineering teams to integrate with existing systems and unblock dependencies.
• Write clear, reliable, well-tested code that ships quickly and scales well.

Software Engineering, Artificial Intelligence (AI), Insurance, Small Business, Business Growth, Philosophy, Artificial Intelligence (AI), Product Design, Modeling Languages, Team Building, * 7+ years of software engineering experience building and shipping production products or platforms

• Hands-on experience implementing LLM-powered features (e.g., RAG flows, agents, tool loops, workflow automation with language models, etc)
• Strong engineering skills (e.g., services, APIs, data flows); comfortable spending most of your time coding.
• Experience running or heavily contributing to a team’s execution: sprints, Jira, scoping, and cross-functional coordination.
• Bias to action: you default to trying things, iterating, and learning, rather than getting stuck in analysis or waiting for direction.
• Clear communicator who can work well with product, design, and other engineering teams without needing a formal management title.
• Experienced with Ruby on Rails (or any comparable language), React (or any comparable library).

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.

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto’s subsidiary, whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.

When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.

Reliable, consistent presence: We expect regular and predictable attendance, whether you’re working in-office, hybrid, or fully remote, so that you stay closely connected to your team, customers, and stakeholders in real time and ensure colleagues and customers receive the timely support and responsiveness they deserve.