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. 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