Head of Forward Deployed Engineering

Ledgebrook is seeking a Head of Forward Deployed Engineering to lead the hands-on deployment, scaling, and adoption of production AI and agentic software across our core business units.

In this role, you will lead a high-autonomy team of engineers responsible for embedding directly with operational leaders—from underwriting to finance—to scope, prototype, and ship high-impact AI workflows that business teams actually use. You will serve as the crucial bridge between field reality and our core platform architecture, combining deep technical mastery of modern agentic frameworks (like Claude Code, LangGraph, and CrewAI) with executive business literacy. Exceptional leadership, a builder-first mindset, and a relentless focus on tangible adoption metrics rather than vanity demos are essential for success in this position.

Must Haves

• 8+ years of production software engineering experience, with recent (last 1–2 years) of deep, hands-on experience using modern agentic/LLM frameworks (e.g., Claude Code, LangGraph, CrewAI).

• Proven track record of embedding with non-technical business teams to design, ship, and maintain software solutions that teams continuously use in production.

• Solid CI/CD and DevOps fundamentals, with the ability to evaluate, build, and optimize software delivery pipelines.

• Strong business analysis skills, capable of translating messy, ambiguous processes (spreadsheets, manual workflows, tribal knowledge) into well-scoped technical solutions without hand-holding.

• Demonstrated leadership and teaching capabilities, including experience leading small engineering teams in high-autonomy environments while remaining an active builder.

• High adaptability and business literacy, comfortable operating as the most technical person in a room of operational leaders and the most business-literate person in a room of engineers on the same day.

Nice To Haves

• Prior insurance or insurtech domain exposure (e.g., familiarity with actuarial, underwriting, claims, or reinsurance workflows).

• Experience operating in high-growth startup environments with high tolerance for ambiguity and rapid context-switching.

• Direct experience establishing data governance, classification, or compliance constraints in production software environments.