Lead Server Administrator

Jackson Dawson is looking for a Lead Server Administrator to own the design, deployment, and day-to-day health of our hybrid server environment. You'll be the senior technical voice on the Infrastructure team — bridging on-premises Windows Server with Microsoft Azure IaaS across multiple sites, and serving as the go-to escalation point for anything server-related. This is a hands-on, deeply technical role for someone who enjoys running the platform, mentoring the team around them, and partnering closely with IT Security, Development, and PMO to keep the business running.

Responsibilities

• Windows Server & Virtualization
  • Deploy, configure, and manage Windows Server 2016/2019/2022 across on-premises and Azure IaaS (with light AWS support).
  • Administer VMware vSphere 9 (ESXi hosts and vCenter): VM provisioning, snapshots, resource allocation, DRS/HA cluster health, and host maintenance.
  • Own the server lifecycle end-to-end: patching (BatchPatch), firmware updates (Dell OpenManage), hardware maintenance, and decommissioning.
  • Maintain server build standards, CIS baseline hardening, and clean configuration documentation.
• Active Directory & Identity
  • Administer Active Directory Domain Services — domain controllers, sites and services, replication, and schema.
  • Design, deploy, and troubleshoot Group Policy Objects with a regular review cadence for compliance.
  • Manage DNS (AD-integrated zones, conditional forwarders, reverse lookup, split-brain DNS) and DHCP (scopes, reservations, failover).
  • Run Entra ID (Azure AD) hybrid identity: Entra Connect sync, hybrid join, and Conditional Access in partnership with IT Security.
  • Enforce least-privilege access across on-prem and Azure AD user, group, and OU structure.
• Microsoft Azure IaaS
  • Manage Azure IaaS resources: Virtual Machines, Virtual Networks, NSGs, Load Balancers, Azure Bastion, and Storage.
  • Administer Resource Groups, subscription cost management, and tagging governance.
  • Configure and maintain Azure Site Recovery for DR across HQ and the secondary site.
  • Manage Azure DNS zones, Private Endpoints, and VNet peering for hybrid connectivity.
  • Support hybrid connectivity via VPN Gateway and/or ExpressRoute alongside the on-premises networking team.
• IIS & Web Server Administration
  • Install, configure, and maintain IIS for internal and externally-facing web applications.
  • Manage application pools, bindings, SSL/TLS certificates (including renewal workflows), and HTTPS configuration.
  • Troubleshoot IIS performance, failed request tracing, event log analysis, and HTTP errors.
  • Apply IIS hardening standards: remove unnecessary modules, configure request filtering, manage app permissions.
  • Partner with Development on deployment configurations, dependencies, and dev/staging/prod parity.
• SQL Server Infrastructure
  • Administer SQL Server at the OS and infrastructure layer: installation, patching, service accounts, and Windows-level performance.
  • Configure and maintain HA/DR infrastructure — Always On Availability Groups, Failover Cluster Instances, and witness/quorum.
  • Manage SQL Server network configuration, SQL Browser, firewall rules, and named instance connectivity.
  • Partner with DBAs on storage provisioning, tempdb placement, I/O configuration, and server-level resource governance.
  • Monitor Windows Event and SQL Error logs for infrastructure issues; escalate database-layer issues to the DBA team.

  Note: This role owns SQL Server infrastructure. Database administration (schema, query tuning, backup jobs, agent jobs) is handled by the DBA function.

• Backup, DR & Business Continuity
  • Own and operate the enterprise backup platform (Veeam Backup & Replication or equivalent) — job scheduling, retention, and media management.
  • Run and document regular backup verification and test restores; maintain RTO/RPO logs.
  • Design and maintain DR runbooks for all critical workloads across HQ and the AA2 secondary site.
  • Administer Azure Site Recovery replication, failover testing, and failback procedures.
  • Coordinate DR tabletop exercises with IT leadership and produce post-exercise remediation plans.
• Monitoring, Observability & Log Management
  • Own our monitoring stack: Grafana, GrayLog, and VMware Tools (vSphere 9).
  • Deploy monitoring agents and data collectors across every managed endpoint — physical servers, VMs, and desktop workstations.
  • Build and maintain Grafana dashboards covering CPU, memory, disk I/O, network throughput, and service availability across physical, virtual, and Azure IaaS workloads.
  • Configure Grafana alerting rules, notification channels, and escalation policies so the right people hear about the right thresholds.
  • Administer GrayLog for centralized log ingestion, parsing, and storage — inputs, extractors, streams, and pipelines for Windows Event, IIS, application, and syslog sources.
  • Partner with IT Security on GrayLog retention and SIEM integration.
  • Manage VMware Tools across all guest VMs; feed guest performance metrics into Grafana.
  • Maintain a complete monitoring-coverage inventory: every managed device must have a confirmed agent and active check-in.
  • Establish and document performance baselines by device class; use them to spot drift, capacity trends, and pre-failure indicators.
  • Respond to monitoring-triggered incidents; document RCA and remediation for all P1/P2 events.
  • Produce monthly infrastructure health and coverage reports for IT leadership.
• Automation & Scripting
  • Build and maintain PowerShell scripts for provisioning, patch reporting, compliance checking, DNS auditing, and account management.
  • Maintain a version-controlled, documented script library and contribute to the IT automation roadmap.
  • Support CI/CD pipeline infrastructure in coordination with Development (Azure DevOps) where provisioning intersects with pipeline needs.
• Security & Compliance
  • Apply and maintain CIS benchmark hardening on all managed servers; support IT Security with vulnerability remediation.
  • Manage server-level firewall rules, Windows Defender configuration, and local security policy in line with IT Security standards.
  • Support audit and compliance requests — inventory, access reports, patch compliance, and log exports.
• Documentation & Technical Leadership
  • Keep infrastructure documentation accurate and current: network/server diagrams, IP/DNS inventory, runbooks, change records, and SOPs.
  • Mentor junior Infrastructure and Help Desk staff on server and systems topics.
  • Lead infrastructure projects end-to-end: scoping, design, implementation planning, and post-implementation review.
  • Participate in IT governance and change management under IT leadership.

Requirements

• 8+ years of progressively responsible Windows server and systems administration in enterprise environments.
• Demonstrated experience administering hybrid environments spanning on-premises Windows Server and Microsoft Azure IaaS.
• Strong hands-on expertise in Active Directory, DNS, DHCP, and Group Policy in multi-site environments.
• Proven IIS administration experience, including SSL/TLS certificate management and web application server configuration.
• Practical experience with enterprise backup platforms (Veeam strongly preferred) and documented DR processes including test restores.
• SQL Server infrastructure experience: installation, patching, Always On Availability Groups, and Failover Clustering.
• Proficiency in PowerShell scripting for administration and automation.
• Experience providing technical mentorship or informal leadership to junior team members.

Preferred Qualifications

• Microsoft certifications: AZ-800 (Hybrid Infrastructure), AZ-104 (Azure Administrator), MCSA/MCSE Windows Server, or equivalent.
• Experience with Azure DevOps in an infrastructure context (pipelines, infrastructure-as-code coordination).
• Familiarity with IT governance, change management, and ITIL-aligned service management.
• Experiential marketing or agency environment experience is a plus.

What Success Looks Like — First-Year OKRs

• Q1 Foundation & Assessment
  • Establish a complete, accurate inventory of all managed server assets (on-prem and Azure) with documented configuration baselines.
  • 100% of production servers documented in CMDB/asset system within 60 days.
  • Server hardening audit completed against CIS benchmarks; remediation backlog created and prioritized.
  • All backup jobs validated with documented test restores for Tier 1 workloads.
• Q2 Reliability & Automation
  • Reduce manual administrative burden and improve platform consistency through automation.
  • PowerShell automation deployed for patch compliance reporting, DNS auditing, and AD user account review.
  • Server patch compliance rate ≥ 95%, reported monthly to IT leadership.
  • IIS SSL certificate renewal automated or formally tracked with zero expiry events.
• Q3–Q4 DR Maturity & Hybrid Optimization
  • Validate and mature disaster recovery posture across both sites.
  • Full DR tabletop exercise completed for HQ and AA2 failover scenarios; gaps documented.
  • Azure Site Recovery replication verified for all Tier 1 workloads with documented RTO/RPO targets.
  • SQL Server Always On AG health verified and failover test executed with documented results.

Work Environment

Jackson Dawson is an experiential marketing agency operating in a fast-paced, project-driven environment. This role supports IT operations across multiple physical sites and involves managing competing priorities. On-site in Dearborn, MI. Occasional off-hours availability is required for