Hybrid opportunity at
GustoStaff Software Engineer, Gustie Assist
Gusto is a company focused on strengthening the small business economy by providing essential services such as payroll, health insurance, 401(k) plans, and HR tools to…
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About This Role
Gusto is a company focused on strengthening the small business economy by providing essential services such as payroll, health insurance, 401(k) plans, and HR tools to over 500,000 customers nationwide. The organization is seeking a Staff Software Engineer to join the Gustie Assist team in San Francisco. This hybrid role involves working within a small platform unit that builds Otto, an artificial intelligence agent designed to assist support advocates in…
Job Description
Gusto is a company focused on strengthening the small business economy by providing essential services such as payroll, health insurance, 401(k) plans, and HR tools to over 500,000 customers nationwide. The organization is seeking a Staff Software Engineer to join the Gustie Assist team in San Francisco. This hybrid role involves working within a small platform unit that builds Otto, an artificial intelligence agent designed to assist support advocates in resolving complex compliance, payroll, and benefits challenges for small businesses.
This position requires an engineer who is comfortable handling broad, hands-on applied AI development. Responsibilities span across managing the large language model agent runtime, the surrounding full-stack architecture, tool layers, and evaluation mechanisms that ensure safe interactions with live accounts. The role suits an experienced technologist eager to move ideas into production rapidly while focusing heavily on user outcomes rather than model novelty.
Full-time employees at Gusto receive competitive base compensation, equity in the form of restricted stock units, and employee benefits. Candidates should expect to work on a hybrid schedule requiring attendance at the San Francisco office on designated days roughly two to three times per week.
Responsibilities
- Design and build components of the Otto platform, covering the runtime, agent graph, tool layer, Rails and GraphQL backend, and the advocate-facing frontend
- Expand autonomous agent capabilities safely through tool-using actions supported by human-in-the-loop approvals and secure identity models
- Construct evaluation and observability systems, including LLM-as-judge, deterministic scorers, offline gates, and online production monitoring
- Work directly with large language models on prompting, function design, retrieval systems, and feedback loops
- Partner closely with product, data, design, and customer experience teams to translate user pain points into production capabilities
- Mentor other engineers and establish high standards for building reliable, scalable agentic systems
Requirements
- Typically 8 or more years of software engineering experience owning end-to-end systems
- Demonstrated experience building and deploying production-grade large language model or agentic systems, including tool-calling, retrieval, or evaluations
- Strong full-stack capability ranging from backend services and LLM runtimes to customer-facing products
- Experience leading multi-quarter projects that deliver measurable scale and user impact
- Sound judgment regarding safety and blast radius when software executes actions on real accounts
- Ability to mentor peers and elevate technical standards
Qualifications
- Experience with agent frameworks, evaluations, LLM-as-judge methodologies, retrieval, or model context protocol style tool architectures
- Familiarity with Ruby on Rails or JavaScript and React
- Familiarity with GraphQL and federated backends
- Appreciation for collaborative, test-driven environments with high autonomy
Core Skills
Benefits
- Competitive base pay
- Equity in the form of restricted stock units
- Comprehensive employee benefits
Frequently Asked Questions
What is the employment type for this role?
This position is a full-time job.
Where is the job located and what is the remote policy?
The role is based in San Francisco with a hybrid remote status. Employees based in San Francisco are expected to work from the office approximately two to three days per week on designated days.
What is the salary for this position?
The job posting does not specify a salary amount, noting only that offer amounts depend on the role, level, and location.
What kind of experience is required?
The position typically requires 8 or more years of software engineering experience owning systems end-to-end, along with practical experience building and shipping LLM-powered or agentic systems in production.
Sample Interview Questions
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