About the Role

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.

Work environment: On-Site (Dearborn, MI)

What You'll Do

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.

What You'll Bring

Qualifications

• 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

• 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 60; 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. Occasional off-hours availability is required for scheduled maintenance windows, incident response, and DR testing.

This job description is intended to convey information essential to understanding the scope of the position. It is not an exhaustive list of responsibilities, duties, skills, or qualifications. Jackson Dawson reserves the right to modify this document at any time.