Lead DevOps Engineer

Logistics:

Type: Contract-to-hire (or extend)

Location: close to the Cities of Boston, Mass. St. Louis, Missouri , Tampa, Fla or Newark, New Jersey

Interview Process: 1 maybe 2

GC or Citizen only, may convert

For this lead DevOps Engineer position candidates should have experience in both the stack we’re moving from (to help optimize current workloads until we’re in the cloud) as well as having heavy experience in AWS and ideally several certifications.

For these interviews, I want to do the initial screen of 45 minutes and then choose to progress them or not. The team they will be working with is one of the most constrained teams in the company and I need to be very sensitive of their time.

Senior Cloud DevOps Engineer (Modernization)

Role Summary

We are seeking a Senior Cloud DevOps Engineer to support our migration of on-premises Windows, .NET, and SQL Server workloads to AWS. You will collaborate with architects, security, and development teams to design and deliver secure, automated, and observable cloud solutions, while providing technical guidance to fellow engineers.

Key Responsibilities

• Design and implement Infrastructure as Code using AWS CDK to enable automated, repeatable cloud provisioning.
• Build and maintain CI/CD pipelines using GitHub Actions, YAML, and PowerShell.
• Manage GitHub repositories, branching strategies, pull requests, and release workflows.
• Administer and integrate JFrog Artifactory for artifact management and container image storage.
• Automate provisioning, configuration management, and deployments using Ansible.
• Deploy and optimize workloads across AWS and Azure, including Windows Services and .NET applications.
• Support current Windows Server, IIS, and SQL Server environments, including database creation, backups, restores, and queries.
• Implement cloud security best practices, including secure networking, IAM, secret management, and compliance controls.
• Integrate security scanning tools such as Veracode into CI/CD pipelines.
• Contribute to architecture discussions, design reviews, and migration planning alongside architecture team members, helping reach well-reasoned, collaborative decisions.
• Support modernization efforts, including moving Windows and IIS workloads toward containers and managed services where appropriate.
• Help establish reusable patterns, such as shared CDK constructs, reusable workflows, and standardized Ansible roles.
• Mentor team members through code reviews, pairing, and knowledge sharing.
• Use AI-assisted tools such as ChatGPT and Cursor to improve productivity and delivery.

Required Skills & Experience

• 7+ years of relevant experience, including experience in a senior or technical lead capacity.
• Strong hands-on experience with AWS core services, including EKS, IAM, VPC, EC2, and related managed services.
• Proven experience with container technologies (Docker, Kubernetes) in production environments.
• Expertise in CDK workflows, CI/CD pipeline engineering using GitHub Actions or similar tools.
• Experience with GitHub repository management, branching strategies, and DevOps workflows.
• Hands-on experience with JFrog Artifactory for artifact lifecycle management and container registries.
• Strong experience with Ansible for infrastructure automation and configuration management.
• Solid scripting skills in PowerShell and experience authoring YAML-based workflows.
• Experience deploying and supporting Windows-based and .NET workloads in cloud environments.
• Strong understanding of DevSecOps principles, including automated security scanning and compliance.
• Experience using AI-assisted engineering tools such as ChatGPT, GitHub Copilot, and similar platforms to improve productivity and operational efficiency.
• Ability to work cross-functionally and contribute to continuous improvement initiatives.

Technical Skills

• Infrastructure as code: AWS CDK v2 (TypeScript), CloudFormation, and CDK CLI preferred.
• Programming and scripting: TypeScript, Node.js/npm, Python, PowerShell, Bash, and AWS CLI preferred.
• Configuration management: Ansible for Windows (roles, playbooks, YAML/Jinja templates) and AWS Systems Manager Session Manager connections preferred.
• Windows administration: Windows Server, Windows Services, IIS application pools, sites, virtual directories, and network shares.
• CI/CD platforms: GitHub Actions workflows (including reusable workflows and AWS OIDC role assumption), AWS CodePipeline, CodeBuild, and CodeConnections preferred.
• IaC test framework: Jest (including AWS CDK assertions) or similar; TypeScript compilation, ESLint, and Prettier preferred.
• IaC security scanning: Wiz preferred (replacing Checkov for CloudFormation in our pipelines); Semgrep and Trivy or similar.
• Container build, registry, and orchestration: Docker, Buildx for CI-built Ansible runner images, Amazon ECR, and ECS/Fargate preferred.
• Cloud networking and ingress: AWS VPCs, subnets, security groups, ALB, NLB, AWS WAF, Route 53, ACM/TLS, and Global Accelerator preferred.
• Cloud identity, secrets, and encryption: AWS IAM and permissions boundaries, GitHub OIDC, KMS, Secrets Manager, Systems Manager Parameter Store, and CyberArk credential integration preferred.
• Databases and data pipelines: Aurora PostgreSQL/RDS, Microsoft SQL Server on EC2, Amazon Keyspaces for Apache Cassandra, S3 for shared/artifact storage, and AWS Glue preferred.
• SQL Server administration and querying: Database creation, backups, restores, and SQL querying expected.
• Event-driven services: EventBridge/Scheduler, SNS/SQS, and Lambda preferred.
• Observability: CloudWatch logs, metrics, alarms, and dashboards; AWS Systems Manager OpsCenter alarm actions; New Relic; and Splunk Universal Forwarder preferred.

Nice to Have

• Multi-cloud experience (AWS and Azure)
• Exposure to AI/ML platform services
• Experience with internal developer platforms or self-service provisioning
• Strong troubleshooting and performance optimization skills

Certifications

• Highly Desired: AWS Certified Solutions Architect – Associate or Professional
• AWS Certified DevOps Engineer – Professional
• Nice to Have: Additional role-related certifications