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Gusto

Runs payroll and HR software for small businesses

Staff Software Engineer - Gustie Assist

AI Application Engineering +1Confirmed live in the last 24 hours
Full-time

About the Job

Requirements

  • Typically 8+ years of software engineering experience, owning systems end-to-end.
  • Experience building and shipping LLM-powered or agentic systems in production, including tool-calling or agents, retrieval, or evaluations, and understanding their failure modes and reliability needs.
  • Strong full-stack range, with comfort moving between backend services, an LLM runtime, and customer-facing product, and adapting to the problem's 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 them.

Responsibilities

  • 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 through autonomous, tool-using actions with human-in-the-loop approval, built on a secure, auditable identity and permissions model.
  • Build the evaluation and observability systems, including LLM-as-judge and deterministic scorers, offline gates, and online production monitoring, to enable weekly production changes without regressing correctness or escalation behavior.
  • Work directly with LLMs, including prompting, tool/function design, retrieval, and feedback loops that improve Otto using real advocate interactions.
  • Partner with Product, Data, Design, and CX teams to turn advocate and customer pain into shipped capabilities.
  • Mentor engineers and set standards for building agentic systems responsibly and at scale.

Desired Qualifications

  • Experience with agent frameworks, evaluations/LLM-as-judge, retrieval, or MCP-style tool architectures.
  • Experience with Ruby on Rails and/or JavaScript/React, or the ability to ramp quickly.
  • Familiarity with GraphQL and federated backends.

About the Company

Gusto

Runs payroll and HR software for small businesses

Gusto runs payroll, benefits administration, and HR software for small and midsize businesses that want to manage their teams in one place. Its payroll system calculates wages and taxes, files required forms, and connects employee hours with pay runs. Employers use the same platform to enroll workers in health insurance and retirement plans, manage time off, and organize hiring paperwork, while staff access paystubs through personal accounts. Businesses pay monthly subscription fees based on their plan and workforce size, with extra charges for selected services and faster payment options. Gusto was founded in 2011 and is headquartered in San Francisco, California.

Company size
1,001-5,000
Company stage
Series E
Total funding
$706.2M
Headquarters
San Francisco, CA
Founded
2011

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