Head of Forward Deployed Engineering
About The Position
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.
Requirements
- 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.
Responsibilities
- Embed Across Core Business Units: Run an ongoing, flexible rotation through departments—scoping, prototyping, and shipping production-ready AI use cases alongside business leads rather than following a rigid cadence.
- Build Reusable Tooling & Accelerators: Develop internal prompt libraries, tool-integration patterns, and retrieval architecture to accelerate subsequent prototype delivery from weeks down to days.
- Lead a High-Autonomy Engineering Team: Build and guide a small team of engineers, strategically dividing embedded assignments across teams and business priorities while remaining hands-on.
- Bridge Field Reality and Platform Architecture: Feed key learnings, data classification constraints, and operational realities back into the broader AI platform and tool-selection architecture.
- Drive Agentic Coding Best Practices: Partner with engineering leads to define quality standards, review/QA discipline, and CI/CD integration points (automated testing, PR reviews, pipeline triage) for tools like Claude Code.
- Deliver Hands-On Technical & Business Training: Design and execute actionable training and follow-up office hours for engineers and business users that drive real behavior change and adoption.
- Track Metric-Driven Impact: Measure success through active adoption and business impact metrics per department and engineering team, steering clear of vanity usage stats.
Benefits
- Full remote flexibility and asynchronous work culture
- Unlimited PTO and fully paid sick leave
- Comprehensive health benefits, including medical, dental, and vision coverage, plus HSA and FSA options
- Additional financial protection and retirement benefits, including a 401(k), company-paid life insurance, and disability coverage
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
