Staff Software Engineer, Gustie Assist

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

Additional information

At Gusto, we don't use titles the traditional way, as a signal of rank or hierarchy. Instead, our titles describe two things at once - your craft (what you do, e.g. Engineering, Design) and your scope of ownership (what you're accountable for) - which is why you'll see something like "Head of X" instead of a rank word like "Director" that tells you neither.

Because of this, the title on this posting may look different from what you'd expect based on the scope and seniority of the role, and from how similar roles are typically titled elsewhere. If you have questions about how this role compares to your current title or level, your recruiter can help translate.

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.

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.

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