Staff AI Engineer at Fieldguide

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.

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