High Autonomy Jobs in Kentucky (NOW HIRING)

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.

What You’ll Do:

• 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.

We love working with people who are eager to learn constantly and genuinely excited about the chaotic, rewarding process of building a company from the ground up.

You’ll be a great fit if you bring:

• A Strong Moral Compass: You believe in doing the right thing, period. We have a strict zero-tolerance policy for toxic behaviors
• Customer-First Empathy: You are passionate about delivering an exceptional experience to everyone you work with, both inside and outside the company
• Intellectual Curiosity: You naturally question the status quo and love finding innovative ways to solve problems
• A Growth Mindset: You possess a hunger for continuous learning and want to constantly expand your skillset
• Urgency & Prioritization: You can pivot quickly and balance the need to get things right with the speed of getting them done right now
• A Solution-Oriented Outlook: When things go wrong, you don't look for blame—you immediately focus on how to fix it
• Transparent Communication: You value honesty, clarity, and open feedback
• Team-First Energy: You want to win together as a high-performing team and actively build connections across our remote locations

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.

• 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

• The base salary range for this position is $200,000-250,000 per year. This is a good-faith compensation range based on what Ledgebrook reasonably expects to pay for this position at the time of this posting. Actual compensation may vary based on a variety of relevant factors including but not limited to experience, qualifications and geographic location
• Employees in this position are eligible to participate in Ledgebrook’s equity incentive program

For Candidates Applying From The U.S.:

Please note: This position is open only to candidates who are authorized to work in the United States without the need for current or future employer-sponsored work authorization. We are unable to offer sponsorship at this time.

Ledgebrook may use Artificial Intelligence (“AI”) as part of the job application process, including to assist us in evaluating your application. AI is used as a support tool, and hiring decisions are made by human recruiters. By submitting your information, you acknowledge that the company may use AI tools as part of our evaluation. If you need a reasonable accommodation or alternative review process because of a disability or other legally protected basis, contact hiring@ledgebrook.com. Requesting an accommodation will not negatively affect your application.