Staff AI Engineer
About Us
Fieldguide is establishing a new state of trust for global commerce and capital markets by automating and streamlining the work of assurance and audit practitioners—specifically in cybersecurity, privacy, and financial audits. We build software for the people who enable trust between businesses.
We're based in San Francisco, CA, and built remote-first. We're backed by Goldman Sachs Alternatives, Bessemer Venture Partners, 8VC, Floodgate, Y Combinator, and more. Over 50 of the top 100 accounting and consulting firms trust Fieldguide to power mission-critical work.
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.
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.
What You’ll Own
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
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.
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