Staff Software Engineer, Gustie Assist

About Gusto

At Gusto were 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 500000 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.

Gustie Assist builds Otto the AI agent that Gustos support advocates rely on to solve customers hardest payroll benefits and compliance problems. When a small business hits a wall and reaches out the advocate turns to Otto: it reasons over the customers full context answers in the moment and increasingly takes real actions across Gustos systems on the advocates behalf to make the customer whole. Were a small platform team building an agent that reasons acts and has to get it right when the stakes are someones payroll.

This is unusually broad hands-on applied-AI work: youll own an LLM agent runtime and the full stack around it including the tool layer that lets it act over Gustos systems the Rails/GraphQL backend the advocate-facing frontend and the eval system that keeps it trustworthy while it touches live customer accounts. We keep the path from idea to production short and measure ourselves on customer outcomes not model novelty.

• Design and build across the Otto platform including the runtime and agent graph the tool/action layer the Rails/GraphQL backend and the advocate-facing experience owning a meaningful slice end-to-end
• Expand what the agent can safely do: autonomous tool-using actions with human-in-the-loop approval built on a secure auditable identity and permissions model
• Build the eval and observability systems (LLM-as-judge deterministic scorers offline gates and online production monitoring) that let us change the agent in production weekly without regressing correctness or escalation behavior
• Work directly with LLMs including prompting tool/function design retrieval and the feedback loops that turn real advocate interactions into a better Otto
• Partner closely with Product Data Design and our CX teams to turn advocate and customer pain into shipped capabilities
• Mentor engineers and set the bar for how we build agentic systems responsibly and at scale

• Typically 8 years of software engineering experience owning systems end-to-end
• Youve built and shipped LLM-powered or agentic systems in production including tool-calling/agents retrieval or evals and you know where they break and how to make them reliable
• Strong full-stack range. Must be comfortable moving between backend services an LLM runtime and customer-facing product and picking up whatever the problem needs
• Experience owning multi-quarter projects that make measurable user impact at scale
• Sound judgment about safety and blast radius when software takes real actions on real accounts
• Ability to mentor engineers and raise the bar around you

• Experience with agent frameworks evals/LLM-as-judge retrieval or MCP-style tool architectures
• Experience with Ruby on Rails and/or JavaScript/React (our stack) or the ability to ramp quickly
• Familiarity with GraphQL and federated backends
• Appreciation for a collaborative test-driven high-autonomy environment and clear communication with engineering and business stakeholders

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 Gustos 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.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds not just because its the right thing to do but because it makes our company stronger. If you share our values and our enthusiasm for small businesses you will find a home at Gusto.

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race color religion national origin age sex (including pregnancy childbirth or related medical conditions) marital status ancestry physical or mental disability genetic information veteran status gender identity or expression sexual orientation or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories consistent with applicable federal state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey please fill out this form and a member of our team will get in touch with you.

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