Staff Software Engineer, Gustie Assist at Gusto in New York City, NY

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 ourTotal 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 Gusto's 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 customer's full context, answers in the moment, and increasingly takes real actions across Gusto's systems on the advocate's behalf to make the customer whole. We're a small platform team building an agent that reasons, acts, and has to get it right when the stakes are someone's payroll.
This is unusually broad, hands-on applied-AI work: you'll own an LLM agent runtime and the full stack around it, including the tool layer that lets it act over Gusto's 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.
Here's what you'll do day-to-day:
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
Here's what we're looking for:
Typically 8+ years of software engineering experience, owning systems end-to-end
You've 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
Also great to have:
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, 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.

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 it's 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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