Director of Engineering

Location: Remote - US or Canada

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 Youll 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 than assigning blame.
• Transparent Communication: You value honesty, clarity, direct feedback, and early communication of risks and trade-offs.
• Team-First Energy: You want to win together as a high-performing team and actively build strong connections across teams, functions, and remote locations.
• Organizational Thinking: You look beyond individual teams and identify patterns, bottlenecks, and opportunities that improve the broader engineering organization.

Requirements

Must haves

• 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.

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 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.

The Tech Stack for this role:

• Languages: Python, TypeScript
• Frontend: React
• Backend: Python, Node.js, FastAPI and related frameworks
• Data Stack: PostgreSQL, MySQL, Kinesis
• Cloud Infrastructure: AWS, Terraform
• DevOps: GitHub Actions, Docker, CI/CD automation
• Tools: GitHub, Jira, Confluence, Jellyfish, Slack
• Emerging Technologies: AI/ML, LLM-enabled workflows, intelligent automation

Benefits

US & Canada Benefits

• Competitive salary + meaningful equity ownership
• 100% employer-paid health insurance
• 100% remote work, 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

For Candidates Applying From The U.S. and Canada:

Please note: This position is open only to candidates who are authorized to work in the United States or Canada 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