Staff AI Engineer
AI summary of the role
Fieldguide is hiring a Staff AI Engineer to define the technical direction of its AI agent layer for audit and advisory workflows.
What you’ll do
- Set the architectural direction for Fieldguide's agentic systems and intelligence layer
- 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
- Establish evaluation standards, observability infrastructure, and reliability frameworks at scale
What you’ll bring
- 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
- Mastery of retrieval architectures, RAG, vector databases, and embedding pipelines
Technologies
TypeScript · Python · LLM · RAG · vector databases · embedding pipelines · OpenAI · Anthropic · Gemini · LangGraph
About Fieldguide
AI-native engagement platform for audit and advisory firms that combines practitioner workflows, client collaboration, and domain-specific agents across regulated assurance work.
Series C · 100–200 people
Source and classification
Internal deployment & tooling · Evidence for this classification:
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.
More from the job description
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 a [... source excerpt omitted ...] nfluence: 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 distribut [... source excerpt omitted ...] utputs 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 bus
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