Senior DevOps Engineer

Title: CloudOps Engineer
Job Type: Contract
Contract Length: TBD
Pay Range: $60 – $80/hr
Start Date: ASAP
Location: Remote (East Coast preference required; requires occasional travel to Boston)

About the Opportunity:

Our client, a mission-driven company dedicated to supporting educators and students, is 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 "paved path" workflows that empower engineering teams. We are looking for a senior-level individual contributor who thrives on building efficient, reliable systems and can balance immediate operational stability with long-term technical debt reduction.

Key Responsibilities & Deliverables:

This role is focused on the successful completion of specific tasks and deliverables. Your responsibilities will include:

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

Required Skills & Experience:

We are looking for someone with a proven track record of successful contract engagements. The ideal candidate will have:

• 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); direct experience migrating legacy workloads (specifically Windows) to AWS is highly preferred.
• 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.

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