Director of Engineering

This is a fully remote position, open to applicants in United States, +1 more country.

📋 Description

• Lead, mentor, and cultivate the skills of Engineering Managers, Technical Leads, and senior individual contributors across various engineering teams.

• Take charge of organizational health, focusing on staffing, structure, technical delivery, capacity, performance, engagement, retention, and succession planning.

• Convert company strategy and priorities into technology roadmaps, investment decisions, and actionable delivery plans.

• Drive execution across multiple teams with defined ownership, milestones, dependencies, success metrics, and accountability.

• Manage technology strategy and ensure the long-term sustainability of systems and services, considering architecture, scalability, reliability, security, performance, and cost.

• Set technical direction, establish architecture standards, and promote engineering best practices.

• Assess designs and trade-offs, identify systemic risks, and guide major technology and architecture decisions.

• Balance product delivery with platform investment, technical debt reduction, reliability, security, compliance, and modernization efforts.

• Implement data-driven engineering practices across development, testing, CI/CD, observability, incident management, documentation, release management, and production support.

• Offer leadership during critical incidents, including escalation, communication, resolution, root-cause analysis, and preventative enhancements.

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

• Manage partnerships with strategic technology vendors and external partners, encompassing evaluations, renewals, integrations, and build-versus-buy decisions.

• Identify opportunities related to emerging technologies, AI, automation, and contemporary engineering practices.

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

• Collaborate with Product, Data, Infrastructure, Security, Finance, Operations, and business leaders to align technology roadmaps and execution strategies.

⛳️ Requirements

• Over 12 years of professional software engineering experience, including substantial experience leading engineering teams and managers.

• More than 5 years of engineering leadership experience, including managing Engineering Managers or overseeing multiple engineering teams.

• Proven success in building, scaling, and nurturing high-performing engineering organizations.

• Strong technical expertise in software architecture, distributed systems, APIs, cloud platforms, data-integrated applications, and production systems.

• Experience in steering architecture and technology strategy across various services, systems, or product areas.

• Demonstrated capacity to convert business strategy and product priorities into technology roadmaps and actionable engineering plans.

• Experience collaborating closely with Product, business stakeholders, and senior leadership on ambiguous and complex business challenges.

• Strong understanding of software development lifecycle practices, CI/CD, testing, observability, reliability, incident management, and operational excellence.

• Experience in designing and delivering scalable, production-grade systems in cloud environments, preferably AWS.

• Proven ability to manage cross-team dependencies, complex initiatives, and competing priorities in a high-growth environment.

• Demonstrated 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.

• Excellent communication skills, with the ability to articulate complex technical issues, risks, investments, and trade-offs to both technical and non-technical audiences.

• Strong sense of ownership and accountability for technology outcomes, from strategy and architecture through to delivery and production operations.

• Previous experience in startup or scale-up environments characterized by high growth and velocity.

• Experience in scaling engineering organizations during significant company growth.

• Background in insurance, fintech, financial services, or another highly regulated industry.

• Familiarity with underwriting, rating, policy administration, claims, financial, or insurance data systems.

• Experience with cloud-native architectures and platforms utilizing AWS, Terraform, Docker, ECS, or Kubernetes.

• Knowledge of modern CI/CD tools such as GitHub Actions, AWS CodePipeline, or Jenkins.

• Exposure to AI/ML systems, generative AI, LLM-driven workflows, and intelligent automation.

• Experience in developing engineering operating models, career frameworks, technical governance, or organizational maturity practices.

• Experience managing cloud, vendor, infrastructure, and technology investment costs.

• Familiarity with 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 plus meaningful equity ownership.

• 100% employer-paid health insurance.

• Fully remote work environment.

• Flexible working hours.

• Unlimited paid time off.

• Significant ownership, autonomy, and the opportunity to shape the engineering organization.

• Direct influence on technology strategy and company growth.