Head of Forward Deployed Engineering

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Ledgebrook

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2021

💸 Finance

💳 Fintech

🛡️ Insurance

💰 Series B on 2024-09

Finance • Fintech • Insurance

Ledgebrook is a tech-enabled E&S managing general agent (MGA) that provides wholesale brokers with a fast and efficient quoting experience. With a focus on speed and technology-driven underwriting solutions, Ledgebrook utilizes advanced modeling and analytics to deliver quotes rapidly and enhance broker submissions. The company offers various insurance products, including general liability, professional liability, and excess casualty coverage, ensuring tailored solutions for specific client needs.

📋 Description

• Lead the hands-on deployment, scaling, and adoption of production AI and agentic software across core business units • Lead a high-autonomy team of engineers embedding with operational leaders from underwriting to finance • Scope, prototype, and ship high-impact AI workflows alongside business leads • Develop internal prompt libraries, tool-integration patterns, and retrieval architecture • Divide embedded engineering assignments across teams and business priorities while remaining hands-on • Feed field learnings, data classification constraints, and operational realities into AI platform and tool-selection architecture • Define agentic coding quality standards, review/QA discipline, and CI/CD integration points • Design and execute technical and business training and follow-up office hours • Measure active adoption and business impact metrics by department and engineering team

🎯 Requirements

• 8+ years of production software engineering experience • Recent (last 1–2 years) deep, hands-on experience with modern agentic/LLM frameworks such as Claude Code, LangGraph, and CrewAI • Proven experience embedding with non-technical business teams to design, ship, and maintain production software solutions • Solid CI/CD and DevOps fundamentals • Ability to evaluate, build, and optimize software delivery pipelines • Strong business analysis skills translating ambiguous processes into well-scoped technical solutions • Demonstrated leadership and teaching capabilities • Experience leading small engineering teams in high-autonomy environments while remaining an active builder • High adaptability and business literacy • Ability to work as the most technical person among operational leaders and the most business-literate person among engineers • Candidates must be authorized to work in the United States without current or future employer-sponsored work authorization • Nice to have: prior insurance or insurtech domain exposure • Nice to have: high-growth startup experience • Nice to have: experience establishing data governance, classification, or compliance constraints

🏖️ Benefits

• Full remote flexibility and asynchronous work culture • Unlimited PTO and fully paid sick leave • Comprehensive health benefits, including medical, dental, and vision coverage • HSA and FSA options • 401(k) • Company-paid life insurance • Disability coverage • Equity incentive program