Staff AI Engineer

San Francisco, United StatesRemote

Requirements

ABOUT THE ROLE 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.
EXPERIENCE We care more about capability and trajectory than years on a resume, but most strong candidates have: - 8+ years shipping production software, with 3+ years leading complex AI/ML systems - Deep expertise in TypeScript, Python, and distributed system design - Proven track record shipping LLM-powered products at enterprise scale -
Experience defining evaluation infrastructure and reliability standards for AI systems - Mastery of retrieval architectures, RAG, vector databases, and embedding pipelines - Hands-on with cutting-edge LLM APIs and agent frameworks (OpenAI, Anthropic, Gemini, LangGraph, etc.) -
when to surface decisions - Nuanced evaluation: Audits require judgment, so feedback structures matter - Explainability: Making AI outputs and reasoning transparent and trustworthy - Complex domains: Navigating compliance and enterprise rigor while moving fast - Shipping daily value: Delivering agent experiences customers use every day

BENEFITS - Competitive compensation with equity - Comprehensive health and wellness
benefits - Flexible time off and work schedules - Technology reimbursements - 401(k) plan - Twice-yearly in-person offsites across the U.S. - Wellness

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.
These principles resonate with you: - Technical depth with organizational influence: You lead through expertise, not authority - Systems thinker: You see second-order effects and design for them - Strong product judgment: You prioritize ruthlessly and keep customer outcomes in focus - Multiplier: You make everyone around you more effective—you don't just ship solo - Principled pragmatism: You know when to push boundaries and when to ship what works - End-to-end ownership: You own outcomes, not just
Experience influencing technical direction across multiple teams or product areas - Track record mentoring senior engineers and growing engineering culture WHAT SHOULD EXCITE YOU - Enterprise-grade reliability: Building systems professionals depend on - Human-in-the-loop design: Knowing when to automate vs.
benefits starting on your first day OUR VALUES - Fearless — Inspire and break down seemingly impossible walls - Fast — Launch fast with excellence; iterate to perfection - Lovable — Deliver happiness and 11-star experiences - Owners — Execute and run the business with ownership - Win-win — Create mutual value and earn trust for life - Inclusive — Scale the best ideas with inclusive teams