Staff AI Engineer, Fieldguide
$240-310k
Offers Equity
Software for assurance & advisory firms
Be an early applicant
Software for assurance & advisory firms
101-200 employees
Be an early applicant
$240-310k
Offers Equity
101-200 employees
Company mission
Fieldguide's mission is to increase trust in commerce and capital markets.
Role
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
- 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
What the job involves
- 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
- 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
- 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
- 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
- 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
Our take
Fieldguide offers a cloud-native collaboration and automation platform for accounting and advisory practices. The idea is to make workflow and collaboration more streamlined, and automate parts of it altogether, for teams working on cybersecurity, risk, and ESG audits.
Fieldguide has launched with a focus on three high-demand and high-growth areas of business. With cybersecurity and ESG in particular seeing increased corporate investment, thanks to the steep costs of error or regulatory non-compliance, demand for tech that can help manage this influx of auditing work is likely to grow fast. Indeed, Fieldguide received an impressive funding injection in 2024 that will help expand the kinds of audits its product applies to, as well as grow its team.
Fieldguide has already netted some key audit and advisory firms as clients, suggesting that the young company is onto something good. Internal productivity tools are booming across multiple industries, with automation also seeing a significant uptake for enterprise businesses. If Fieldguide can successfully manage its scale-up, it could become an important software player.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
55% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Feb 2026
$75m
SERIES C
Mar 2024
$30m
SERIES B
Total funding: $122.4m
Company benefits
- Health
- Dental
- PTO
Company HQ
Eureka Valley, San Francisco, CA
Leadership
Chris Szymansky
(Co-Founder & CTO)Previously co-founded live video streaming platform Vivo, before moving on to work in software development at Fireman Creative. Subsequently held various high level positions, including CTO at JazzHR, and VP of Engineering, Product, and Design at Atrium.
Jin Chang
(Co-Founder & CEO)Originally a Management Consultant at EY, before co-founding blockchain aggregation API company, Bitbutter. Moved on to serve as Chief of Staff at Atrium.
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