Head of Forward Deployed Engineering

Ledgebrook Insurance, LLC (dba Ledgebrook Insurance Agency); United States; On-site; USD 180,000 - 280,000; Full time

Job summary

Ledgebrook Insurance, LLC (dba Ledgebrook Insurance Agency) seeks a remote Head of Forward Deployed Engineering to lead a high-autonomy team. You will manage hands-on deployment, scaling, and adoption of production AI workflows across core business units, ensuring alignment between technical solutions and operational needs.

You will embed across units to scope, prototype, and ship AI use cases, build reusable tooling, and promote best practices through hands-on training for both engineering and

Qualifications

• 8+ years of production software engineering experience with hands-on work in agentic/LLM frameworks.
• Experience collaborating with non-technical business teams to design and maintain software solutions.
• Strong understanding of CI/CD and DevOps for optimizing delivery pipelines.
• Proven leadership in high-autonomy environments while actively building systems.

Responsibilities

• Embed across core business units to scope, prototype, and ship production-ready AI use cases.
• Build reusable tooling and accelerators to streamline prototype delivery and internal processes.
• Deliver hands-on technical and business training to promote adoption and effective usage.

Skills

LLM frameworks

CI/CD

DevOps fundamentals

Leadership

Business analysis

Job description

Leading a high-autonomy team, the remote Head of Forward Deployed Engineering will manage the hands-on deployment, scaling, and adoption of production AI workflows across core business units, ensuring alignment between technical solutions and operational needs.

Key responsibilities

• Embed across core business units to scope, prototype, and ship production-ready AI use cases alongside business leads
• Build reusable tooling and accelerators to streamline prototype delivery and enhance internal processes
• Drive agentic coding best practices and deliver hands‑on technical and business training to promote adoption and effective usage

Required qualifications

• 8+ years of production software engineering experience with recent hands‑on work using modern agentic/LLM frameworks
• Proven track record of collaborating with non‑technical business teams to design and maintain software solutions
• Solid understanding of CI/CD and DevOps fundamentals for optimizing software delivery pipelines
• Strong business analysis skills to translate ambiguous processes into well‑scoped technical solutions
• Demonstrated leadership abilities in high‑autonomy environments while remaining an active builder