Forward Deployed Engineer
Summary
Build and deploy AI agents for insurance agencies, integrating with messy legacy systems and traveling to customer sites to ensure live adoption.
About the Role
This is a seed-stage, Y Combinator-backed insurtech startup building AI agents that handle real operational work inside insurance agencies. As the first US Forward Deployed Engineer, you'll own customer deployments end to end — from uncovering messy, undocumented workflows to shipping production AI agents that run live inside agency operating systems.
This role sits at the intersection of engineering, product, and customer success. You'll be the person who discovers what an agency truly needs, builds the solution, gets it live, and makes sure it sticks. You'll work directly with agency owners and ops leads, and will travel to customer sites regularly.
This is an on-site role based in San Francisco, CA. US citizenship is required. No visa sponsorship is available.
What You'll Do
Own customer deployments from initial scoping through go-live, working directly with agency owners and operations leads to deeply understand how they work.
Build integrations into the systems agencies already use — whether they have clean APIs, outdated docs, or no documentation at all.
Extract tribal knowledge from agency owners, senior staff, and producers, then translate it into system designs and ship them.
Diagnose and resolve customer issues directly, shipping quick fixes and small customizations that make AI agents fit each agency's workflows.
Maintain a tight cadence with customers to surface expansion opportunities and spot patterns across deployments.
Identify failure patterns across accounts and feed fixes back into the core platform so the same problem doesn't get solved twice.
Travel to customer sites to ensure successful deployments and adoption.
What We're Looking For
Must-haves (dealbreakers):
2+ years shipping production code in Python.
At least one AI application deployed to real production users, with experience designing and iterating evals for real-world performance.
Proficiency with APIs, system integrations, and working across multiple interconnected systems.
US citizenship (no visa sponsorship available).
Required skills & experience:
Hands-on experience with LLMs, prompt engineering, and AI agent development.
Experience with voice or telephony stacks (Twilio or similar).
Proven ability to reverse-engineer undocumented systems, work with incomplete documentation, and integrate with legacy or poorly-documented APIs.
Track record of owning projects end to end — from discovery through production deployment and user adoption.
Experience working at an early-stage startup or taking full ownership of ambiguous projects without an established playbook.
Ability to translate domain-specific tribal knowledge and unwritten workflows into concrete technical system designs.
Strong communication skills — comfortable translating between technical and non-technical stakeholders without losing clarity.
Willingness to travel to customer sites.
Nice to have:
Experience fine-tuning models or building custom AI evaluations.
Experience with speech-to-text systems (e.g. Whisper API).
Domain knowledge in insurance, financial services, or B2B SaaS operations.
Experience building reusable connectors, configuration layers, or platform abstractions for multi-customer deployments.
Compensation & Benefits
Salary: $110,000 – $180,000 per year, depending on experience.
Early-stage equity opportunity at a well-funded seed-stage company.
Location
On-site in San Francisco, CA.
Regular travel to customer sites required.
US citizenship required; no visa sponsorship available.