Software Engineer building scalable Java and Spring Boot applications for Newfold Digital’s global web technology products. Designing REST APIs, optimizing databases, and supporting cloud operations.
About the role
- Director of Engineering scaling teams and technology for Ledgebrook’s excess and surplus insurance platform. Shaping architecture, reliability, and engineering strategy across underwriting and operational systems.
Responsibilities
- 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
- 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
- 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
Job title
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Degree requirement
No Education Requirement
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