Azure Systems Administrator

About PrePass

PrePass® is North America's most trusted weigh station bypass and toll management platform. We’re transforming how the transportation industry operates—creating solutions that keep trucks moving safely, efficiently, and compliantly. This means making bold decisions and building systems that support not only fleets but the broader economy. It all starts with enabling commercial vehicles to keep rolling with seamless toll management, weigh station bypass, and safety solutions. It’s what we do best, and we do it to meet the demands of the road every day.

That’s why people join us: our solutions are implemented in real-time, on highways and interstates across the nation, helping fleets go farther, faster. This work challenges and rewards, presenting complex problems that need ambitious answers. We hire bold thinkers with a heart for impact, a passion for progress, and the optimism to shape the future of transportation.

About the role

We’re looking for an Azure Systems Administrator to support and improve our Azure-first infrastructure, centered on Windows Server virtual machines (IaaS), Active Directory Domain Services (AD DS) running on Azure VMs, and identity synchronization using Azure AD Connect. This role owns provisioning, configuration, patching, monitoring, backup/recovery, security posture management, and incident response for systems that support business‑critical services. You’ll partner with engineering, security, and IT operations to keep environments reliable, secure, and scalable.

Essential Responsibilities

Azure IaaS – Windows Server VM administration

• Provision, configure, and maintain Windows Server VMs in Azure, including sizing, performance tuning, disk/storage management, and availability planning
• Perform daily operational health checks (OS integrity, service availability, CPU/memory/disk trends, scheduled task/job success, and event log review)
• Troubleshoot Windows platform issues (services, certificates, networking, DNS, authentication, resource constraints) and coordinate resolution with stakeholders

Patch management & updates (Azure Update Manager)

• Own VM patching operations using Azure Update Manager (maintenance windows, classification-based patching, phased rollouts, restart coordination)
• Monitor patch compliance and remediate failed deployments and “no update data” scenarios
• Communicate scheduled maintenance to stakeholders and execute updates in a controlled, auditable manner

Backup & recovery (Azure Backup)

• Implement and operate Azure Backup for Azure VMs (policy configuration, monitoring, retention governance)
• Perform and document periodic restore tests and recovery procedures to ensure operational readiness

Identity & directory services (AD DS + Azure AD Connect)

• Administer AD DS hosted on Azure VMs (domain controllers): users/groups, OUs, Group Policy (GPO), security groups, and delegated access
• Maintain domain controller health and dependencies (DNS, replication health, time synchronization, patching coordination, operational runbooks)
• Operate and maintain Azure AD Connect (hosted on a Windows VM in Azure): monitor sync health, troubleshoot sync failures, manage scope/filtering, and support upgrades/maintenance
• Maintain documentation/runbooks for configuration, troubleshooting, and recovery procedures

Web and file services (IIS + File Servers)

• Administer and troubleshoot IIS (site/app configuration, bindings/certs, app pools, logging, performance troubleshooting)
• Administer and support Windows File Servers (SMB shares, NTFS/share permissions, access controls, troubleshooting access/performance issues)

Security posture & vulnerability management (Defender for Cloud)

• Use Microsoft Defender for Cloud to monitor security posture, address recommendations, and remediate vulnerabilities
• Contribute to baseline hardening and security improvements aligned to organizational standards

Monitoring, incident response & continuous improvement

• Participate in an on-call rotation; support incident response, service restoration, root cause analysis, and preventative improvements
• Automate repeatable administrative work using PowerShell and Azure-native tooling
• Create and maintain operational documentation (runbooks/SOPs/diagrams/inventories)

Requirements:
Requirements (Must have)

• 3+ years administering Windows Server in production, including Windows Server VMs in Azure
• Hands-on experience with Azure VM operations (provisioning, troubleshooting, performance tuning, lifecycle management)
• Hands-on experience with Azure Update Manager (maintenance windows, phased patching, compliance tracking)
• Hands-on experience with Azure Backup (policy setup, monitoring, restores, retention)
• Hands-on experience with Microsoft Defender for Cloud (recommendations, vulnerability remediation, posture management)
• Hands-on experience administering AD DS (users/groups/OUs, GPO, permissions) on domain controllers running on Azure VMs
• Hands-on experience with Azure AD Connect (monitoring, troubleshooting sync issues, scope/filtering, maintenance/upgrades)
• Hands-on experience administering and troubleshooting IIS
• Hands-on experience administering Windows File Servers (SMB shares + permissions)
• Strong documentation and communication skills; ability to collaborate across IT, engineering, and security teams

Nice to have

• Load balancing experience (design/support/troubleshooting)
• Microsoft Failover Clustering experience (design/support/troubleshooting)
• Azure PaaS experience (e.g., App Services, Functions, Storage, Key Vault, managed databases, etc.)
• Infrastructure as Code experience (Terraform/Bicep/ARM)
• CI/CD operational support experience
• Endpoint/device management tooling experience (Intune / ConfigMgr)
• Certificate lifecycle management and secrets management practices
• Relevant certifications (optional): AZ‑104, Windows/Identity certifications, security-focused certifications

Benefits:
How We Will Take Care of You

• Robust benefit package that includes medical, dental, and vision that start on date of hire.
• Paid Time Off, to include vacation, sick, holidays, and floating holidays.
• 401(k) plan with employer match.
• Company-funded “lifestyle account” upon date of hire for you to apply toward your physical and mental well-being (i.e., ski passes, retreats, gym memberships).
• Tuition Reimbursement Program.
• Voluntary benefits, to include but not limited to Legal and Pet Discounts.
• Employee Assistance Program (available at no cost to you).
• Company-sponsored and funded “Culture Team” that focuses on the Physical, Mental, and Professional well-being of employees.
• Community Give-Back initiatives.
• Culture that focuses on employee development initiatives.

Join Us

At PrePass, our mission drives us.

We invest in relationships. We challenge ourselves to innovate and improve. We win together. Simply put, we live our Core Values.

Ready to help move the transportation industry forward? Join us and let’s drive progress—together.