Staff AI Engineer
About UsFieldguide 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 RoleFieldguide 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 OwnDefine and Drive Technical DirectionSet the architectural direction for Fieldguide's agentic systems and intelligence layerIdentify and resolve systemic gaps that limit reliability, scalability, or product velocityMake high-leverage technical bets and drive them to completion across the organizationEstablish evaluation standards, observability infrastructure, and reliability frameworks at scaleBuild and Ship High-Impact SystemsOwn the most complex, cross-cutting product areas end-to-endDesign agent orchestration and retrieval systems that handle enterprise-grade complexityLead the evolution of Fieldguide's LLM infrastructure: models, prompts, guardrails, and feedback loopsPrototype, validate, and harden novel approaches before sharing with the broader teamDrive Organizational LeveragePartner with Engineering leadership, Product, and Design to shape the AI roadmapCreate reusable platforms, patterns, and tooling that multiply team velocity across the orgIdentify and develop the next generation of senior engineersTranslate long-term product vision into concrete technical strategiesRepresent and Advance the FieldStay at the frontier of LLM and agent research; rapidly evaluate and adopt what mattersBuild internal knowledge and shared understanding of AI system designContribute to Fieldguide's reputation as a technical leader in vertical AIWho You AreYou’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 authoritySystems thinker: You see second-order effects and design for themStrong product judgment: You prioritize ruthlessly and keep customer outcomes in focusMultiplier: You make everyone around you more effective—you don't just ship soloPrincipled pragmatism: You know when to push boundaries and when to ship what worksEnd-to-end ownership: You own outcomes, not just deliverablesExperienceWe 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 systemsDeep expertise in TypeScript, Python, and distributed system designProven track record shipping LLM-powered products at enterprise scaleExperience defining evaluation infrastructure and reliability standards for AI systemsMastery of retrieval architectures, RAG, vector databases, and embedding pipelinesHands-on with cutting-edge LLM APIs and agent frameworks (OpenAI, Anthropic, Gemini, LangGraph, etc.)Experience influencing technical direction across multiple teams or product areasTrack record mentoring senior engineers and growing engineering cultureWhat Should Excite YouEnterprise-grade reliability: Building systems professionals depend onHuman-in-the-loop design: Knowing when to automate vs. when to surface decisionsNuanced evaluation: Audits require judgment, so feedback structures matterExplainability: Making AI outputs and reasoning transparent and trustworthyComplex domains: Navigating compliance and enterprise rigor while moving fastShipping daily value: Delivering agent experiences customers use every dayBenefitsCompetitive compensation with equityComprehensive health and wellness benefitsFlexible time off and work schedulesTechnology reimbursements401(k) planTwice-yearly in-person offsites across the U.S.Wellness benefits starting on your first dayOur ValuesFearless — Inspire and break down seemingly impossible wallsFast — Launch fast with excellence; iterate to perfectionLovable — Deliver happiness and 11-star experiencesOwners — Execute and run the business with ownershipWin-win — Create mutual value and earn trust for lifeInclusive — Scale the best ideas with inclusive teamsCompensation Range: $240K - $310K