As a Cloud & Infrastructure Specialist, you will champion our commitment to operational excellence and play a key role in shaping the culture and capabilities of our emerging DevOps group. With strong technical acumen and sound judgment, you’ll be responsible for resolving complex infrastructure challenges and driving seamless integration, automation, and reliability across our environments. Your expertise will be especially critical in managing and optimizing systems built on Microsoft Windows Server, Microsoft Remote Desktop Services, Microsoft SQL Server, and PostgreSQL, alongside containerized and AWS-hosted infrastructure supporting our production SaaS environments, ensuring they operate securely, efficiently, and at scale to support our industry-leading dealership software solutions.

Requirements

Key Responsibilities

Infrastructure Provisioning & Management

• Design, build, and maintain secure, scalable Windows Server infrastructure across on-premises and cloud environments.
• Administer and optimize Remote Desktop Services (RDS) deployments, including Azure Virtual Desktop (AVD) environments.
• Manage and maintain Microsoft SQL Server and PostgreSQL database instances, including performance tuning, backups, and patching.
• Participate in upgrades and transitions of customer environments to newer technologies.

Cloud & Production Environment Support

• Provision, secure, and maintain infrastructure within AWS (e.g., EC2, VPC, IAM, S3, RDS, CloudWatch), applying cost-optimization and security best practices.
• Deploy, manage, and troubleshoot containerized workloads (e.g., Docker, Kubernetes/ECS) to support scalable, portable infrastructure.
• Contribute to and help maintain CI/CD deployment pipelines for each of our application environments, supporting reliable, repeatable releases.
• Support and maintain the underlying infrastructure for our production dealer software environments, ensuring uptime, performance, and reliability for our customers.
• Collaborate across Azure and AWS environments to standardize monitoring, automation, and deployment practices in a multi-cloud landscape.

Monitoring & Optimization

• Implement centralized monitoring and logging solutions.
• Set up automated alerts and conduct regular performance audits.
• Identify opportunities for automation and efficiency improvements.

Security & Compliance

• Develop and enforce security best practices across on-premises, Azure, and AWS environments.
• Continuously assess vulnerabilities and implement cybersecurity measures.
• Assist in patch management, system updates, and endpoint protection.

Collaboration & Support

• Provide escalation support for production infrastructure issues.
• Work closely with development teams to improve reliability and performance.
• Document procedures, configurations, and troubleshooting steps.
• Mentor and guide team members across the organization.
• Facilitate knowledge transfer and cross-training within the team
• Stay current with industry trends and emerging technologies to drive innovation and efficiency within the organization.
• Participate in on-call rotation, after-hours activities (weekends and evenings), and respond to incidents as needed.

The Kind of Candidate we are looking for:

3+ years of experience in a Windows support or administration role.

• Bachelor’s degree in Computer Science, Information Technology, or related field, or equivalent practical experience.
• Experience with Windows Remote Desktop Services required; familiarity with Azure Virtual Desktop (AVD) is an asset.
• Familiarity with Microsoft Azure (Entra ID, Networking, DevOps, Security) is an asset.
• Experience managing Microsoft SQL Server and/or PostgreSQL in production environments.
• Proficiency in Windows Server OS, Active Directory, Group Policy.
• Familiarity with virtualization technologies (VMware, Hyper-V).
• Experience with core AWS services (e.g., EC2, VPC, IAM, S3, RDS, CloudWatch) in a production environment.
• Experience with containerization technologies (e.g., Docker, Kubernetes) is an asset.
• Familiarity with CI/CD tools such as GitHub Actions is an asset.
• PowerShell scripting and automation experience.
• Excellent troubleshooting and problem-solving skills.
• Strong communication and collaboration abilities.
• Microsoft Azure certification (e.g., AZ-140) is an asset.
• AWS certification (e.g., AWS Certified SysOps Administrator – Associate or Solutions Architect – Associate) is an asset.

Benefits

Flexible work environment

Remote role