Director of Engineering

About this role

Description
At Ledgebrook, we are building an Excess & Surplus (E&S) lines insurance company that combines deep underwriting and pricing expertise with a modern technology platform fit for the future of insurance — truly a best-of-both-worlds approach. Our speed and service underpin every decision we make, and our rapidly growing team is a testament to our value proposition resonating with the market.
You bring the passion, leadership, and entrepreneurial spirit, and we’ll provide the opportunity to unleash the very best of your talents and skills. Apply now to advance your career at Ledgebrook.
About the Role
We’re looking for an experienced Director of Engineering to lead and scale multiple engineering teams responsible for the technology powering Ledgebrook’s underwriting, policy, rating, data, and operational systems.
The ideal candidate combines strong technical judgment, organizational leadership, and business acumen. You are someone who can develop Engineering Managers and senior technical leaders, shape technology strategy and architecture, create operating discipline across teams, and ensure engineering investments translate into meaningful business outcomes.
You will be accountable not only for what engineering delivers, but also for building the organization, systems, processes, and leadership capability that allow teams to execute predictably and scale as Ledgebrook grows.
You’ll partner 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 our technology platform.
What You'll Do:

• Lead, coach, and develop Engineering Managers, Technical Leads, and senior individual contributors across multiple engineering teams.

• Own organizational health across your 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, ensuring initiatives have clear ownership, milestones, dependencies, success measures, and accountability.

• Own the technology strategy and long-term health of systems and services within your domain, 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 strong data-driven engineering operating practices across development, testing, CI/CD, observability, incident management, documentation, release management, and production support.

• Provide leadership during critical incidents, ensuring effective escalation, communication, resolution, root-cause analysis, and follow-through on preventative improvements.

• Lead quarterly and annual technology planning, including roadmap prioritization, capacity planning, organizational design, and headcount projections.

• Maintain productive relationships with strategic technology vendors and external partners, including involvement in evaluations, renewals, integrations, and build-versus-buy decisions.

• Identify opportunities to leverage emerging technologies, AI, automation, and modern engineering practices to create meaningful business or operational advantage.

• Represent Engineering in leadership discussions, planning forums, operating reviews, and cross-functional initiatives.

About you
We love working with people who are eager to learn constantly and genuinely excited about the chaotic, rewarding process of building and scaling a company from the ground up.
As a Director, you are comfortable operating at multiple levels. You can discuss architecture with senior engineers, coach an Engineering Manager through an organizational challenge, work with Product on roadmap trade-offs, and explain technology investments and risks clearly to business and executive leaders.
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.

• Leadership Through Others: You understand that your impact as a Director comes from building strong leaders, teams, systems, and organizational capability rather than personally owning every decision.

• Business Acumen: You connect engineering decisions to business outcomes and understand how technology investments affect customers, operations, cost, growth, and risk.

• Technical Judgment: You can operate comfortably in architectural and technical discussions, ask the right questions, understand trade-offs, and provide direction without becoming a bottleneck.

• 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 actively seek ways to improve yourself, your leaders, and the organization.

• Urgency & Prioritization: You can make thoughtful decisions quickly and balance long-term technology health with the realities of a fast-moving business.

• A Solution-Oriented Outlook: When things go wrong, you focus on solving the problem, understanding the root cause, and improving the system rather…