Windows Systems Engineer

• Administer Windows Servers across multiple customer environments, including DNS, DHCP, Group Policy, file and print services, and certificate services
• Plan and execute Active Directory work - domain controller upgrades, promotion and demotion, OS and functional-level upgrades, replication troubleshooting, and site and topology changes - from a documented plan
• Write, debug, and maintain PowerShell for provisioning, reporting, bulk changes, and remediation, converting repeat manual work into reusable, reviewed automation
• Administer Microsoft 365 and Entra ID: Exchange Online, mail flow and transport rules, licensing, mailbox moves and migrations, group and identity management, and Conditional Access policy
• Own patch cadence across servers and endpoints, maintain endpoint protection coverage, and remediate vulnerability scan findings against agreed timelines
• Support MFA and Conditional Access rollouts and maintain identity hygiene, including privileged account control, stale object cleanup, and access reviews
• Monitor backup and replication jobs, run and evidence test restores, and escalate failures against RPO and RTO commitments
• Build, standardize, and retire Windows servers across virtualization and cloud IaaS, including image standards and capacity planning
• Operate the VMware vSphere or Hyper-V estate: host and cluster health, VM lifecycle and sizing, snapshots, datastore capacity, and hypervisor patching within approved maintenance windows
• Act as the L3 escalation point for the service desk, drive root-cause analysis on recurring incidents, and feed fixes back into runbooks
• Follow change management for all infrastructure work: risk assessment, maintenance windows, rollback plans, and post-change validation
• Maintain runbooks, architecture and identity documentation, and configuration records, keeping customer-specific detail current
• Produce and maintain evidence for PCI and HIPAA reviews, including patch reports, restore tests, access reviews, and configuration baselines

• 5+ years hands-on with Windows Server and Active Directory, covering DNS, DHCP, and Group Policy administration
• Demonstrated ability to run a domain controller promotion or upgrade independently from a documented plan, including pre-checks, replication validation, and rollback
• Certificate management experience: AD CS or another internal PKI, public SSL/TLS certificate lifecycle, and the renewal and expiry discipline that keeps customer services from failing on an expired certificate
• PowerShell proficiency at the level of writing and debugging scripts, not only running scripts written by others - or equivalent automation depth in another tool (Python, Ansible, or Terraform) alongside working PowerShell
• Working command of security and patch hygiene: patch cadence, endpoint protection, MFA and Conditional Access concepts, and the ability to read a vulnerability scan and act on it
• Experience supporting PCI- and/or HIPAA-regulated customer environments and the change control and evidence discipline they require
• Microsoft 365 and Entra ID administration, including Exchange Online, mail flow, licensing, mailbox moves, and Conditional Access
• Backup and restore operations: job monitoring, test restores, and failure escalation - Cohesity or Veeam preferred, though the operational discipline matters more than the specific product
• Hands-on virtualization experience with VMware vSphere or Hyper-V, including host and cluster operations, VM provisioning, snapshots, and resource management
• Clear written communication and documentation habits suited to a multi-customer environment
• Bachelor’s degree in information technology, computer science, or equivalent experience

Preferred

• Experience in an MSP, MSSP, or multi-tenant hosting environment supporting several customers concurrently
• Azure IaaS or Azure Virtual Desktop experience alongside on-premises virtualization
• Endpoint and patch management platforms such as Intune, SCCM/MECM, or an RMM such as NinjaOne or Datto
• Vulnerability management tooling (Nessus, Qualys, or Rapid7) and Microsoft Defender for Endpoint or Defender for Office 365
• Experience with RMM, PSA, or ITSM platforms such as NinjaOne, ConnectWise, HaloPSA, Jira Service Management, or ServiceNow
• Hybrid identity experience including Entra Connect, tenant-to-tenant migrations, and Windows Server 2022/2025 upgrade cycles
• Familiarity or working knowledge of using AI coding tools such as Claude or OpenAI to accelerate scripting and troubleshooting
• Certifications such as AZ-104, MS-102, SC-300, AZ-800/801, CompTIA Security+, or MCSA/MCSE

• Health Coverage - Medical, Dental & Vision
• FSA Health and Dependent Care available
• 401(k) Plan
• Unlimited Paid Time Off (PTO)
• Observed Holidays Paid
• Cell Phone Allowance
• Collaborative, growth-driven culture