Staff Artificial Intelligence Engineer

• Fieldguide is building AI agents for the most complex audit and advisory workflows. As a Staff AI Engineer, you’ll shape the technical direction of our intelligence layer—defining the architecture, standards, and roadmap that enable Fieldguide to build the most reliable AI agents in the enterprise
• This role is for experienced engineers who combine deep technical judgment with strong product instincts and organizational influence. You’ll operate across the engineering organization to drive impact that compounds over time
• Define and Drive Technical Direction
• Set the architectural direction for Fieldguide’s agentic systems and intelligence layer
• Identify and resolve systemic gaps that limit reliability, scalability, or product velocity
• Make high-leverage technical bets and drive them to completion across the organization
• Establish evaluation standards, observability infrastructure, and reliability frameworks at scale
• Build and Ship High-Impact Systems
• Own the most complex, cross-cutting product areas end-to-end
• Design agent orchestration and retrieval systems that handle enterprise-grade complexity
• Lead the evolution of Fieldguide’s LLM infrastructure: models, prompts, guardrails, and feedback loops
• Prototype, validate, and harden novel approaches before sharing with the broader team
• Drive Organizational Leverage
• Partner with Engineering leadership, Product, and Design to shape the AI roadmap
• Create reusable platforms, patterns, and tooling that multiply team velocity across the org
• Identify and develop the next generation of senior engineers
• Translate long-term product vision into concrete technical strategies
• Represent and Advance the Field
• Stay at the frontier of LLM and agent research; rapidly evaluate and adopt what matters
• Build internal knowledge and shared understanding of AI system design
• Contribute to Fieldguide’s reputation as a technical leader in vertical AI

Benefits

• Health
• Dental
• PTO- Shipping daily value: Delivering agent experiences customers use every day
• Hands-on with cutting-edge LLM APIs and agent frameworks (OpenAI, Anthropic, Gemini, LangGraph, etc.)
• What Should Excite You
• Multiplier: You make everyone around you more effective—you don’t just ship solo
• Complex domains: Navigating compliance and enterprise rigor while moving fast
• 8+ years shipping production software, with 3+ years leading complex AI/ML systems
• Strong product judgment: You prioritize ruthlessly and keep customer outcomes in focus
• Experience defining evaluation infrastructure and reliability standards for AI systems
• End-to-end ownership: You own outcomes, not just deliverables
• Deep expertise in TypeScript, Python, and distributed system design
• Human-in-the-loop design: Knowing when to automate vs. when to surface decisions
• Track record mentoring senior engineers and growing engineering culture
• Technical depth with organizational influence: You lead through expertise, not authority
• Systems thinker: You see second-order effects and design for them
• Proven track record shipping LLM-powered products at enterprise scale
• Experience influencing technical direction across multiple teams or product areas
• Experience
• Nuanced evaluation: Audits require judgment, so feedback structures matter
• Mastery of retrieval architectures, RAG, vector databases, and embedding pipelines
• Enterprise-grade reliability: Building systems professionals depend on
• You’re a strong software engineer who’s built your skills for an AI-native world. These principles resonate with you:
• Explainability: Making AI outputs and reasoning transparent and trustworthy
• Principled pragmatism: You know when to push boundaries and when to ship what works
• We care more about capability and trajectory than years on a resume, but most strong candidates have: