Director of Engineering

Ledgebrook

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

Posted 10/23/2026full-timeRemote • United States, CanadaLeadWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive experience in leading engineering teams and developing high-performing organizations, with a strong technical background in software architecture, cloud platforms, and modern engineering practices. Proven ability to translate business strategies into actionable technology roadmaps while ensuring operational excellence and compliance in regulated environments.

Highest-signal resume keywords

Engineering LeadershipSoftware ArchitectureCloud Platforms (AWS)CI/CD PracticesStakeholder Collaboration

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Software EngineeringDistributed SystemsAPIsData-Integrated ApplicationsProduction SystemsCloud-Native ArchitecturesTechnical GovernanceIncident ManagementCapacity PlanningOrganizational Design

Soft Skills

Strong CommunicationCoaching and MentoringOwnership and Accountability

Tools & Technologies

AWSTerraformDockerECSKubernetesGitHub ActionsAWS CodePipelineJenkins

Industry Keywords

InsuranceFintechFinancial ServicesRegulated Technology EnvironmentsSOC 2 Compliance

Tech Stack

Tools & technologies

AWSCloudDistributed SystemsDockerJenkinsKubernetesTerraform

About the role

Key responsibilities & impact

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

What you’ll need

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

Comp & perks

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