Note: The job is a remote job and is open to candidates in USA. DeWinter Group is a mission-driven company dedicated to supporting educators and students, and they are seeking a hands-on, strategically minded CloudOps Engineer for a contract engagement. This role focuses on modernizing legacy infrastructure, stabilizing core development environments, and building workflows that empower engineering teams.

Responsibilities

• Drive the modernization of legacy infrastructure, specifically guiding the migration from Windows-based environments to AWS
• Build and evolve "paved paths" for service creation, deployment, and observability, improving the developer experience through CI/CD automation, repo templates, and container workflows
• Automate system patching, maintenance tasks, and infrastructure management (including identifying unused infrastructure)
• Implement and manage alerting systems for critical infrastructure issues (e.g., disk space, policy upgrades) and integrate observability tools like Datadog or New Relic
• Stabilize and enhance the Cloud Development Environment (CDE) for .NET Framework development while establishing patterns for scalable, reliable, and well-automated infrastructure
• Collaborate with the security team to implement secure defaults and guardrails without acting as a gatekeeper

Skills

• 8+ years of engineering experience, including 3+ years leading platform, cloud infrastructure, SRE, or DevOps initiatives
• Strong experience with AWS (Compute, Networking, IAM, Storage, Databases)
• Proficiency in Infrastructure as Code (Terraform, CloudFormation, or CDK)
• Deep understanding of containerized applications (Docker, ECS/EKS) and CI/CD pipelines (GitHub Actions)
• Practical experience with modern observability (metrics, logs, traces; CloudWatch, Datadog, or Grafana)
• A product mindset, with the ability to balance trade-offs between security, reliability, cost, and developer velocity
• Excellent communication skills, with a track record of mentoring team members, building trust, and navigating ambiguity within a collaborative engineering culture
• Direct experience migrating legacy workloads (specifically Windows) to AWS is highly preferred

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