Staff Software Engineer

Jobtailor; California (MO); On-site; USD 180,000 - 240,000; Full time

Job summary

Jobtailor seeks a senior engineer to design and ship LLM-powered systems across the Otto platform, including runtime and agent graphs, tool action layers, and Rails/GraphQL backends.

You will own end-to-end platform slices, extend agent capabilities with human-in-the-loop approvals, and build observability, evaluation and monitoring systems for production use.

Qualifications

• Typically 8+ years of software engineering experience owning systems end-to-end.

Responsibilities

• Own a meaningful slice of the Otto platform end-to-end.
• Expand autonomous, tool-using actions with human-in-the-loop approval.
• Mentor engineers and set standards for responsible, scalable agentic systems.
• Partner with Product, Data, Design, and CX teams to ship capabilities.

Skills

LLM-Powered Systems

Mentoring Engineers

Tool-Calling/Agents

Evaluations/LLM-As-Judge

Retrieval

Agent Frameworks

Production Monitoring

Multi-Quarter Project Management

Clear Communication

Collaborative Working Style

Sound Judgment

Data Collaboration

Product Management

Customer Experience (CX)

Ruby On Rails

JavaScript/React

Tools

Ruby on Rails

JavaScript/React

GraphQL

Observability Systems

Offline Gates

Online Production Monitoring

Tool-Calling/Agents

Retrieval

Agent Frameworks

MCP-style Tool Architectures

Job description

• Design and build across the Otto platform, including the runtime and agent graph, tool/action layer, Rails/GraphQL backend, and advocate-facing experience
• Own a meaningful slice of the platform end-to-end
• Expand autonomous, tool-using actions with human-in-the-loop approval using secure, auditable identity and permissions
• Build evaluation and observability systems, including LLM-as-judge, deterministic scorers, offline gates, and online production monitoring
• Work with LLMs on prompting, tool/function design, retrieval, and feedback loops
• Partner with Product, Data, Design, and CX teams to turn advocate and customer pain into shipped capabilities
• Mentor engineers and set standards for responsible, scalable agentic systems

Requirements

• Typically 8+ years of software engineering experience owning systems end-to-end
• Production experience building and shipping LLM-powered or agentic systems, including tool-calling/agents, retrieval, or evaluations
• Strong full-stack range across backend services, an LLM runtime, and customer-facing products
• Experience owning multi-quarter projects with measurable user impact at scale
• Sound judgment about safety and blast radius when software takes real actions on real accounts
• Ability to mentor engineers
• Experience with agent frameworks, evaluations/LLM-as-judge, retrieval, or MCP-style tool architectures is advantageous
• Experience with Ruby on Rails and/or JavaScript/React, or ability to ramp quickly
• Familiarity with GraphQL and federated backends
• Collaborative, test-driven, high-autonomy working style and clear communication with engineering and business stakeholders

Core Competencies

Demonstrates extensive experience in building and shipping LLM-powered systems, with a strong full-stack capability across backend services and customer-facing products. Proven ability to mentor engineers and lead multi-quarter projects that deliver measurable user impact at scale.

Highest-signal resume keywords

• LLM-Powered Systems
• Ruby On Rails
• JavaScript/React
• GraphQL
• Mentoring Engineers

ATS Optimization Keywords

Hard Skills

• Software Engineering
• Full-Stack Development
• Tool-Calling/Agents
• Evaluations/LLM-As-Judge
• Retrieval
• Agent Frameworks
• Production Monitoring
• Test-Driven Development
• Scalable Agentic Systems
• Multi-Quarter Project Management

Soft Skills

• Clear Communication
• Collaborative Working Style
• Sound Judgment

Industry Keywords

• Human-In-The-Loop Approval
• Auditable Identity
• Permissions
• Customer Experience (CX)
• Product Management
• Data Collaboration

Tools & Technologies

• Otto Platform
• Agent Graph
• Runtime
• Action Layer
• Observability Systems
• Deterministic Scorers
• Offline Gates
• Online Production Monitoring