AI Engineer

Fieldguide is redefining trust in global commerce by modernizing how cybersecurity, privacy, and financial audits are done. We build AI-powered software that empowers audit and advisory practitioners—automating and streamlining their work to deliver faster, higher-quality results.

We’re a remote-first company headquartered in San Francisco, CA, backed by top investors including Bessemer Venture Partners, 8VC, Y Combinator, Floodgate, Elad Gil, and more. Our team values diversity of backgrounds and experiences, and we’re deliberate about building an inclusive, humble, and high-performing culture.

We’re hiring AI Engineers across multiple levels to help design, build, and scale our intelligent document understanding, reasoning, and agentic systems. Depending on your experience and interests, you may contribute as a mid-level engineer, take on leadership within a team, or drive technical strategy across teams and systems. The final level will be determined during the interview process based on scope and demonstrated experience.

You’ll collaborate with engineers, and product managers to ship features powered by the latest advancements in LLM and retrieval-augmented generation (RAG). This is an opportunity to have outsized impact at a company with clear product-market fit and massive growth potential, taking on legacy audit and accounting tools that are decades old, widely disliked, and ripe for disruption.

• Design, build, and deliver AI-powered features that drive customer and business impact

• Develop and maintain LLM-based systems powering Fieldguide’s core product experiences

• Collaborate cross-functionally with engineers, PMs, and designers to turn complex problems into elegant, user-focused solutions

• Balance iteration speed with long-term maintainability and system health

• Continuously improve our AI stack, developer workflows, and evaluation practices

• Contribute to a supportive, growth-oriented engineering culture based on trust, learning, and excellence

• Strong software engineering fundamentals and experience shipping data-driven, LLM, or agentic systems to production

• Familiarity with foundational LLM APIs such as Anthropic or OpenAI.

• Writing maintainable, well-tested, and observable code for both experimentation and production environments

• Sound judgment around tradeoffs, reliability, and performance

• Ability to scope, prioritize, and deliver work that moves business outcomes

• Comfortable working across the lifecycle of AI features—from prototyping and evaluation to deployment and monitoring

• Clear and proactive communication around progress, risks, and decisions

• Ownership mindset—following work through from ideation to production and iteration

• Empathy for teammates and customers; contributes positively to team culture

• Open to feedback and committed to continuous improvement

• Works effectively across disciplines and functions to achieve shared goals

• Communicates clearly about complex technical concepts to nontechnical stakeholders

• Embodies Fieldguide’s values: Fearless, Fast, Lovable, Owners, Win-win, Inclusive

• Mentors and supports peers; contributes to hiring and onboarding processes

• Curious and self-driven in learning new skills, technologies, and domains

• Takes increasing ownership—from building models and infrastructure to shaping architecture and mentoring others—as you grow

• Lead the creation of complex LLM-powered systems, setting technical direction and ensuring long-term health

• Collaborate with PMs and designers to shape roadmaps and define architectural tradeoffs

• Serve as a domain expert within one or more technical areas (e.g., model evaluation, RAG architecture, or data systems)

• Mentor other engineers and help raise the technical bar across the team

• Drive company-level technical initiatives and influence cross-team AI architecture

• Set and champion engineering standards for scalability, security, and performance in AI systems

• Partner with engineering and product leadership to define long-term AI strategy

• Serve as a trusted advisor to leaders across Engineering, Product, and Design

• Represent Fieldguide externally through writing, speaking, and open-source contributions

• Experience or familiarity with audit, assurance, or risk management domains

• Working with RAG pipelines or multimodal document understanding

• Building evaluation pipelines and ground-truth datasets for generative systems

• Working with unstructured, domain-specific data (e.g., PDFs, images, spreadsheets)

• Experience with data labeling, annotation tooling, or active learning

• Shaping a new AI stack, product, or engineering org from the ground up

• Applying information security and compliance principles (SOC 2, FedRAMP, PCI)

• Competitive compensation packages with meaningful equity ownership

• Comprehensive health and wellness benefits, including free therapy sessions

• Flexible PTO and work schedules

• Technology & work-from-home reimbursements

• 401(k) plan

• Twice-yearly in-person offsites across the U.S.

Fearless — Inspire & break down seemingly impossible walls
Fast — Launch fast with excellence; iterate to perfection
Lovable — Deliver happiness & 11-star experiences
Owners — Execute & run the business with ownership
Win-win — Create mutual value & earn trust for life
Inclusive — Scale the best ideas with inclusive teams