Staff AI Engineer

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

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

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

You’re a strong software engineer who’s built your skills for an AI-native world. 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 deliverables

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.)

Experience influencing technical direction across multiple teams or product areas

Track record mentoring senior engineers and growing engineering culture

Enterprise-grade reliability: Building systems professionals depend on

Human-in-the-loop design: Knowing when to automate vs. 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

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