Director of Engineering

Ledgebrook

9d • Remote

About The Position

Ledgebrook is building an Excess & Surplus lines insurance company that combines underwriting and pricing expertise with a modern technology platform. The Director of Engineering will lead and scale multiple engineering teams responsible for technology supporting underwriting, policy, rating, data, and operational systems.

This role combines technical judgment, organizational leadership, and business acumen. The Director will develop Engineering Managers and senior technical leaders, shape technology strategy and architecture, establish disciplined operating practices, and ensure engineering investments deliver meaningful business outcomes. The role is accountable for engineering delivery as well as building the organization, systems, processes, and leadership capability required to execute predictably as the company grows.

The Director will work closely with Product, Data, Infrastructure, Security, Finance, Operations, and business leaders to translate company priorities into technology roadmaps and execution plans while maintaining the reliability, scalability, security, and long-term health of the technology platform. The position is 100% remote with flexible hours and is open to candidates authorized to work in the United States or Canada without current or future employer-sponsored work authorization.

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.
• 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; AWS is preferred.
• Experience managing cross-team dependencies, complex initiatives, and competing priorities in a high-growth environment.
• 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 skills, including the ability to explain complex technical issues, risks, investments, and trade-offs to technical and non-technical audiences.
• Strong ownership and accountability for technology outcomes from strategy and architecture through delivery and production operations.

Nice To Haves

• Prior startup or scale-up experience in a high-growth, high-velocity environment.
• Experience scaling engineering organizations through significant company growth.
• Experience in 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.

Responsibilities

• Lead, coach, and develop Engineering Managers, Technical Leads, and senior individual contributors across multiple engineering teams.
• Own organizational health across the engineering domain, including staffing, structure, technical delivery, capacity, performance, team engagement, retention, and succession planning.
• Partner with Product and business leaders to translate company strategy and priorities into technology roadmaps, investment decisions, and executable delivery plans.
• Drive execution across multiple teams by establishing clear ownership, milestones, dependencies, success measures, and accountability.
• Own technology strategy and the long-term health of systems and services, including architecture integrations, scalability, reliability, security, performance, and cost.
• Partner with Principal Engineers, Architects, Engineering Managers, and Technical Leads to establish technical direction, architecture standards, and engineering best practices.
• Maintain sufficient technical depth to challenge designs, evaluate 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 operating 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, including roadmap prioritization, capacity planning, organizational design, and headcount projections.
• Maintain relationships with strategic technology vendors and external partners, participating in evaluations, renewals, integrations, and build-versus-buy decisions.
• Identify opportunities to use emerging technologies, AI, automation, and modern engineering practices to create business or operational advantages.
• Represent Engineering in leadership discussions, planning forums, operating reviews, and cross-functional initiatives.

Benefits

• Competitive salary and meaningful equity ownership.
• 100% employer-paid health insurance.
• 100% remote work and flexible hours.
• Unlimited paid time off.
• Work with an ambitious, smart, fun team to transform a $1T global industry.
• Significant ownership, autonomy, and opportunity to shape the engineering organization.
• Direct influence on technology strategy and company growth.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed