Forward Deployed Engineer

Department: Engineering

Location: remote

Employment Type: FullTime

About the Role

This is a founding customer-facing engineering role at a Y Combinator–backed insurtech AI startup (seed stage, small team) building AI agents that handle real, production work inside insurance agencies. As the first US Forward Deployed Engineer, you'll own customer deployments end to end — from scoping and discovery through go-live and ongoing adoption. The role sits at the intersection of product, engineering, and customer success, and is ideal for someone who thrives in ambiguity, loves shipping things that work in the real world, and enjoys getting deep into customer operations.

This is an on-site / travel-required role. You must be a US citizen or have a valid US work visa. Visa sponsorship is not available.

What You'll Do

• Own customer deployments from initial scope through go-live, working directly with agency owners and operations leads to understand how they actually run their business.

• Build integrations into the systems agencies already use — whether those systems have clean APIs, outdated docs, or no documentation at all.

• Extract tribal knowledge from domain experts and senior staff, then translate it into system designs and ship them.

• Diagnose and resolve customer issues directly, shipping quick fixes and small customizations to make AI agents fit agency-specific workflows.

• Maintain a tight customer cadence to surface expansion opportunities and spot patterns across deployments.

• Feed recurring failure patterns back into the core platform so the same problem doesn't get solved twice.

• Travel to customer sites to drive successful deployments and adoption.

What We're Looking For

Must-haves:

• 2+ years shipping production code in Python.

• At least one AI application deployed to real users, including experience designing and iterating evals for real-world performance.

• Strong proficiency with APIs and system integrations across multiple interconnected systems.

• Experience with LLMs, prompt engineering, and AI agent development.

• Demonstrated ability to reverse-engineer undocumented systems and work with incomplete or legacy API documentation.

• Track record of owning projects end to end — from discovery through production deployment and adoption — without an established playbook.

• Experience working at an early-stage startup or taking ownership of genuinely ambiguous projects.

• Ability to translate domain-specific, unwritten workflows into technical system designs.

• Strong communication skills — equally comfortable with agency owners and fellow engineers.

• Willingness and ability to travel to customer sites.

• US citizenship or valid US work authorization required (no sponsorship available).

Strong pluses:

• Experience with voice or telephony stacks (e.g. Twilio or similar).

• Experience with speech-to-text systems or the Whisper API.

• Fine-tuning models or building custom AI evaluations.

• 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 (USD), depending on experience.

• Early-stage equity opportunity at a well-backed seed-stage company.

Location

Based in the United States. This is an on-site role with travel to customer sites required. Candidates should be comfortable being present at customer locations as part of regular work.