Staff AI Engineer

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

Who You Are

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

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.)
• 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. 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 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