Head of Forward Deployed Engineering at Ledgebrook

Job description

Description Ledgebrook is an AI-native specialty insurance platform. When a business needs coverage that is custom and complex, its broker comes to us, and our underwriters give them an answer, often in hours rather than weeks. We built our technology from scratch, with AI in it from the first line of code. The technology helps price the risk; the underwriter uses their judgment to decide. There are always two hands on the wheel. We are insurance industry insiders, and we eat our own cooking: Ledgebrook writes the policy and shares the risk through our own carrier, Ledgebrook Specialty, rated A- (Excellent) by AM Best. We work exclusively through wholesale brokers. Our vision: to make the wheels of insurance spin faster. At Ledgebrook, everything we do is driven by our culture: Care, Strive, Thrive Together. To succeed in modernizing the industry, we must first succeed in changing the way we do business. Talent density is our north star—fewer, better people working together as one. To that end we’ve replaced all individual incentives with generous equity packages—we play as a team, we win as a team. Everyone benefits handsomely from Ledgebrook’s success. About the Role 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. About you 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 Requirements 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. Benefits US 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 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. Compensation Compensation • 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

Requirements

Must-haves

Ledgebrook is an AI-native specialty insurance platform. When a business needs coverage that is custom and complex, its broker comes to us, and our underwriters give them an answer, often in hours rather than weeks.
We built our technology from scratch, with AI in it from the first line of code. The technology helps price the risk; the underwriter uses their judgment to decide. There are always two hands on the wheel.
Our vision: to make the wheels of insurance spin faster.
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.
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.
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
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).

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.

Application prep

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Keywords to mirror

aici/cdgollm

Platform: comeet
Effort: medium

Benefits

Benefits detected in the listing.

Dental

Vision

401(K)

Pto