Director of Engineering

Job not on LinkedIn

🕒 Yesterday

🌐 United States, Canada – Remote

🇺🇸 United States – Remote 🇨🇦 Canada – Remote

⏰ Full Time

🔴 Lead

🖥 Software Engineer

👻 Ghost score 10%

What it means: how likely this posting is sitting open without active hiring.How to read it: 60% or higher means we think this is a ghost. Lower scores are less of a worry.How we score it: age, reposts, open roles vs team size, how fast jobs close, and whether pay is listed.Fine print: an estimate from public data, not a judgment of the company. Real jobs can score high, so treat it as a hint, not a fact.

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Ledgebrook

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2021

🛡️ Insurance

🤝 B2B

💸 Finance

💰 $65M Series C on 2025-07

Insurance • B2B • Finance

<Ledgebrook> is a tech-enabled Excess & Surplus (E&S) managing general agent (MGA) that provides fast, data-driven quoting and underwriting services to wholesale brokers. Ledgebrook combines a next-generation tech stack, modeling and analytics, and experienced underwriters to deliver rapid, streamlined submissions and casualty products such as general liability and professional liability.

📋 Description

• Lead, coach, and develop Engineering Managers, Technical Leads, and senior individual contributors across multiple engineering teams • Own organizational health, including staffing, structure, technical delivery, capacity, performance, engagement, retention, and succession planning • Translate company strategy and priorities into technology roadmaps, investment decisions, and executable delivery plans • Drive execution across multiple teams with clear ownership, milestones, dependencies, success measures, and accountability • Own technology strategy and the long-term health of systems and services, including architecture, scalability, reliability, security, performance, and cost • Establish technical direction, architecture standards, and engineering best practices • Evaluate designs and trade-offs, identify systemic risks, and guide significant technology and architecture decisions • Balance product delivery with platform investment, technical debt reduction, reliability, security, compliance, and modernization • Establish data-driven engineering practices across development, testing, CI/CD, observability, incident management, documentation, release management, and production support • Provide leadership during critical incidents, including escalation, communication, resolution, root-cause analysis, and preventative improvements • Lead quarterly and annual technology planning, roadmap prioritization, capacity planning, organizational design, and headcount projections • Manage relationships with strategic technology vendors and external partners, including evaluations, renewals, integrations, and build-versus-buy decisions • Identify opportunities involving emerging technologies, AI, automation, and modern engineering practices • Represent Engineering in leadership discussions, planning forums, operating reviews, and cross-functional initiatives • Partner with Product, Data, Infrastructure, Security, Finance, Operations, and business leaders to align technology roadmaps and execution plans

🎯 Requirements

• 12+ years of professional software engineering experience, including significant experience leading engineering teams and managers • 5+ years of engineering leadership experience, including experience managing Engineering Managers or leading multiple engineering teams • Demonstrated success building, scaling, and developing high-performing engineering organizations • Strong technical background in software architecture, distributed systems, APIs, cloud platforms, data-integrated applications, and production systems • Experience leading architecture and technology strategy across multiple services, systems, or product areas • Demonstrated ability to translate business strategy and product priorities into technology roadmaps and executable engineering plans • Experience partnering closely with Product, business stakeholders, and senior leadership on ambiguous and complex business problems • Strong understanding of software development lifecycle practices, CI/CD, testing, observability, reliability, incident management, and operational excellence • Experience designing and delivering scalable, production-grade systems in cloud environments, preferably AWS • Proven experience managing cross-team dependencies, complex initiatives, and competing priorities in a high-growth environment • Proven ability to recruit, coach, mentor, and develop Engineering Managers, senior engineers, and technical leaders • Experience with workforce planning, organizational design, capacity planning, and headcount prioritization • Strong communication, with the ability to explain complex technical issues, risks, investments, and trade-offs to technical and non-technical audiences • Strong sense of ownership and accountability for technology outcomes from strategy and architecture through delivery and production operations • Prior startup or scale-up experience in a high-growth, high-velocity environment • Experience scaling engineering organizations through significant company growth • Experience with insurance, fintech, financial services, or another highly regulated industry • Experience with underwriting, rating, policy administration, claims, financial, or insurance data systems • Experience with cloud-native architectures and platforms using AWS, Terraform, Docker, ECS, or Kubernetes • Experience with modern CI/CD tooling such as GitHub Actions, AWS CodePipeline, or Jenkins • Exposure to AI/ML systems, generative AI, LLM-driven workflows, and intelligent automation • Experience developing engineering operating models, career frameworks, technical governance, or organizational maturity practices • Experience managing cloud, vendor, infrastructure, and technology investment costs • Experience supporting SOC 2, security, compliance, or other regulated technology environments • Candidates must be authorized to work in the United States or Canada without current or future employer-sponsored work authorization

🏖️ Benefits

• Competitive salary + meaningful equity ownership • 100% employer-paid health insurance • 100% remote work • Flexible hours • Unlimited paid time off • Significant ownership, autonomy, and opportunity to shape the engineering organization • Direct influence on technology strategy and company growth