GovCIO’s Kearneysville hiring blitz for a Journeyman Windows System Administrator puts a familiar, high‑stakes mix of legacy Windows operations, enterprise virtualization, and DoD‑grade security squarely in the spotlight — a hybrid role that demands hands‑on Windows Server and VMware experience, active or transferable Secret clearance, and the kind of automation and compliance know‑how that large federal programs increasingly require.
Over the past five years federal contractors supporting DoD and U.S. Coast Guard (USCG) programs have leaned heavily on experienced Windows systems administrators who can combine day‑to‑day server ops with automation, stringent STIG/DoD hardening, and platform migration planning. GovCIO’s posting for a Journeyman Windows System Administrator reflects that reality: it lists core responsibilities such as installing and maintaining Windows Server 2016/2019+, managing VMware vSphere environments, deploying and securing Remote Desktop Services (RDS), and running patch/compliance automation with TrueSight Server Automation (TSSA). The role also stresses DoD‑specific security validation — alignment with DoD 8570/8140 baselines and support inside UNCLAS and other DoD network enclaves.
This job sits at the junction of operational continuity and modernization. Agencies still run mission‑critical workloads on supported but aging Windows Server branches, while program owners push for virtualization refreshes, hardened RDS access, and automated compliance workflows to reduce human error and audit risk.
Key technical implications for admins:
On certifications: historically the VCP‑DCV (VMware Certified Professional – Data Center Virtualization) has been the recognized credential for vSphere-centric administrators. VMware’s certification program has evolved, and employers tend to value either a current VCP track or demonstrable vSphere experience. Candidates should check the current VMware certification roadmap and note that Broadcom’s stewardship of VMware certification has led to changes in exam names and tracks — but practical, demonstrable vSphere experience remains the hiring currency.
Operational tips for virtualization work in DoD/USCG contexts:
Security and licensing considerations that commonly trip up programs:
Practical notes for administrators using TSSA in a DoD environment:
Administratively important points:
Essential best practices:
Employers should be mindful that pay bands must reflect both clearance premiums and the deep, cross‑platform operational experience the role requires; under‑compensating for the clearance/skill set risks longer vacancy times and operational risk during transitions.
For hiring managers, success will come from realistic scopes of work that reconcile Microsoft lifecycle realities, automation staffing, and the non‑trivial complexity of integrating RDS and patch orchestration into a STIG‑driven environment. For candidates, the path to being competitive is clear: document clear, verifiable operational wins, maintain required certifications and clearance status, and be ready to demonstrate both automation expertise and airtight documentation practices on day one.
Source: Dice https://www.dice.com/job-detail/5b3873bf-2771-4edc-8081-cc673a87bda4/
Background
Over the past five years federal contractors supporting DoD and U.S. Coast Guard (USCG) programs have leaned heavily on experienced Windows systems administrators who can combine day‑to‑day server ops with automation, stringent STIG/DoD hardening, and platform migration planning. GovCIO’s posting for a Journeyman Windows System Administrator reflects that reality: it lists core responsibilities such as installing and maintaining Windows Server 2016/2019+, managing VMware vSphere environments, deploying and securing Remote Desktop Services (RDS), and running patch/compliance automation with TrueSight Server Automation (TSSA). The role also stresses DoD‑specific security validation — alignment with DoD 8570/8140 baselines and support inside UNCLAS and other DoD network enclaves.This job sits at the junction of operational continuity and modernization. Agencies still run mission‑critical workloads on supported but aging Windows Server branches, while program owners push for virtualization refreshes, hardened RDS access, and automated compliance workflows to reduce human error and audit risk.
What the job tells us: responsibilities and immediate technical demands
The bulletin is a useful snapshot of what modern federal Windows admin roles now demand on a daily basis.- Install, configure and maintain Windows Server (2016, 2019, and newer) in enterprise environments.
- Administer VMware vSphere/ESXi/vCenter, including virtual networking and storage integration.
- Deploy, secure and troubleshoot Remote Desktop Services (RDS) infrastructures (Gateways, Licensing, Session Hosts).
- Use TrueSight Server Automation (TSSA) for patch automation, configuration enforcement and compliance jobs.
- Administer Active Directory (GPOs, DNS, DHCP) and perform domain health monitoring.
- Apply DoD/USCG hardening standards, STIGs, and vulnerability remediation practices.
- Operate in UNCLAS and secure DoD network environments with an Active Secret clearance required or eligible.
Why Windows Server versions matter right now
Windows Server 2016 and 2019 still power a massive number of government workloads, but product lifecycle timing matters for planning and risk management. Microsoft’s lifecycle documentation shows Windows Server 2016 enters extended support sunset windows through early 2027, while Windows Server 2019 enjoys extended servicing further into the decade. That reality forces contractors and program managers to balance immediate operational stability against migration risk. Administrators working on these stacks must therefore plan for staged upgrades, interim mitigations, and careful patch windows that align with both Microsoft’s lifecycle and agency modernization timelines.Key technical implications for admins:
- Patch cadence and ESUs: Understanding Microsoft’s support timeline and any Extended Security Update (ESU) programs is essential when justifying the cost/benefit of delaying an OS migration.
- Application compatibility: Legacy applications and third‑party integrations may constrain upgrade windows; test and compatibility scripts are non‑negotiable.
- STIG/hardening drift: Older OS builds require more aggressive STIG remediation and continuous monitoring to stay compliant.
Virtualization: VMware vSphere expectations and the certification landscape
Managing VMware vSphere environments is a core item in the posting — ESXi hosts, vCenter operations, VM lifecycle, and integrated storage/networking are all cited. Administrators must troubleshoot host failures, manage DRS/HA clusters, and coordinate firmware/driver compatibility across hardware stacks. Those responsibilities remain central to keeping mission workloads resilient.On certifications: historically the VCP‑DCV (VMware Certified Professional – Data Center Virtualization) has been the recognized credential for vSphere-centric administrators. VMware’s certification program has evolved, and employers tend to value either a current VCP track or demonstrable vSphere experience. Candidates should check the current VMware certification roadmap and note that Broadcom’s stewardship of VMware certification has led to changes in exam names and tracks — but practical, demonstrable vSphere experience remains the hiring currency.
Operational tips for virtualization work in DoD/USCG contexts:
- Keep host/firmware catalogs and compatibility matrices up to date.
- Treat vCenter and ESXi patching as staged, tested changes with rollback plans.
- Maintain configuration backups for hosts and vCenter, and document maintenance runbooks rigorously.
Remote Desktop Services at scale: security, licensing, and operational realities
RDS remains a common approach for delivering applications and desktops to dispersed users. The job’s emphasis on RDS — gateways, licensing, and session hosts — is practical: agencies need secure remote access paths that are both auditable and resilient. Microsoft’s RDS documentation outlines the core roles (RD Gateway, RD Connection Broker, RD Session Host, RD Licensing, RD Web Access) and provides deployment guidance that administrators in this role will need to follow. Proper certificate management, load balancing, and session broker high availability planning are essential for production RDS environments.Security and licensing considerations that commonly trip up programs:
- RD Gateway certificates and TLS configuration: RD Gateway commonly sits at the internet edge and must use certificates that match public FQDNs and adhere to modern TLS policies.
- RDS licensing compliance: Ensure RD CALs are tracked and properly assigned; licensing misconfigurations can threaten user access during audits.
- Hardened RDP surface: Lock down legacy RDP protocols and cipher suites; test STIGs against RDS role services to avoid service disruptions from overly strict hardening.
TrueSight Server Automation: automation at enterprise scale
GovCIO’s requirement for TrueSight Server Automation (TSSA) experience is notable; TSSA (formerly BladeLogic in many enterprises) remains a heavyweight tool for provisioning, patching, configuration management, and compliance reporting across heterogeneous estates. BMC’s documentation describes how TSSA centralizes jobs, enforces RBAC, and scales to manage large fleets — exactly the capabilities a DoD support contract needs when dealing with thousands of endpoints and strict compliance objectives. Industry product reviews also show that while TSSA is powerful, it requires experienced operators and careful integration planning.Practical notes for administrators using TSSA in a DoD environment:
- Maintain a strict role‑based access model inside TSSA to separate patching, provisioning, and remediation duties.
- Integrate TSSA with vulnerability scanners (e.g., Tenable or Qualys) and your security operations workflows to automate remediation tickets where possible.
- Test NSH/agent scripts in staging before broad rollout; automation mistakes at scale can cause system outages.
DoD security baselines, STIGs, and the certification floor: DoD 8570 / 8140 context
The job lists DoD 8570 IAT Level II equivalence (e.g., Security+ CE, CySA+) — a common contractual baseline for technician‑level IT security responsibilities. While DoD policy has evolved (DoD 8140 replaced some of the 8570 language), the underlying expectation holds: personnel with privileged access must hold an approved baseline certification. ISC2 and training providers reflect the matrix that maps job functions to acceptable certs. Candidates should verify the specific baseline required by the contract and be prepared to present certification documentation during onboarding and periodic audits.Administratively important points:
- Keep certification records current and traceable; many federal contracts will ask for contractor certification listings during audit windows.
- Understand the difference between baseline certification requirements and program‑specific credentials or training (e.g., sponsor‑provided STIG training).
- Employers may accept equivalent or higher credentials — a CISSP or CASP+ will typically exceed IAT Level II minimums.
Operational resilience: backup, recovery, documentation, and runbooks
The role’s call for backup and recovery testing, runbooks, SOPs, and diagrams is a reflection of mission‑critical uptime expectations. For USCG/DoD programs the paperwork is not mere bureaucracy — it’s the blueprint that lets teams recover quickly and demonstrate audit‑level readiness.Essential best practices:
- Maintain tested backup and recovery playbooks for AD, RDS collections, vCenter, and critical VMs.
- Keep Change Control and SACL/Audit logs centralized; tie them to incident response playbooks.
- Produce concise runbooks for common operational tasks (e.g., ESXi host remediation, RDS collection scale‑out, certificate rotation).
Hiring process, Clearances, and candidate realities
GovCIO’s posting outlines a multi‑stage screening: virtual interview (camera on), photo ID checks, enhanced biometrics verification, background checks covering the past seven years, and employment/education verification. The job also requires an Active Secret clearance — or the ability to hold one — which materially affects candidate timelines and mobility. For applicants, the clearance requirement means:- Expect a weeks‑to‑months onboarding timeline depending on clearance status and adjudication backlog.
- Keep employment and education records readily available; gaps or inconsistencies slow the process.
- Be prepared for enhanced identity verification (biometrics) as part of the contractor vetting process.
Compensation, market fit, and remote/hybrid realities
The Dice posting for this position lists a base range around USD $80,000–$100,000 per year for the Journeyman role, with senior roles in the same office commanding higher ranges. Comparable listings in the Kearneysville/Berkeley County market show variability based on experience and active clearance status. Candidates with strong VMware, AD, RDS, and TSSA experience — plus a valid DoD IAT Level II certification and an active Secret — will position themselves at the upper end of pay bands.Employers should be mindful that pay bands must reflect both clearance premiums and the deep, cross‑platform operational experience the role requires; under‑compensating for the clearance/skill set risks longer vacancy times and operational risk during transitions.
Risks, red flags, and mitigation for program managers
- Too many legacy dependencies: Heavy reliance on older Windows Server versions or bespoke integrations increases migration risk. Mitigation: schedule phased application testing windows and maintain isolated staging replicates of production.
- Single‑tool automation dependence: Overreliance on a single automation console (e.g., TSSA) without cross‑training creates a single‑person / single‑point‑of‑failure. Mitigation: cross‑train teams and maintain documented manual fallback steps.
- Misconfigured RDS hardening: Overzealous STIG application can break service dependencies; under‑hardening exposes the RDP surface. Mitigation: pair STIG runs with a service validation checklist and rollback plan.
- Certification and clearance gaps: Hiring without required baseline certs or an active clearance slows program readiness. Mitigation: prioritize cleared candidates or present a clear roadmap for certification and interim supervision.
Practical guidance for applicants
- Lead with your clearance and certs. Put Active Secret and IAT Level II / Security+ CE or CySA+ at the top of your resume if you have them.
- Quantify virtualization scale: list clusters, number of hosts, vCenter versions, typical maintenance windows, and major incident remediations.
- Describe RDS ownership: number of session hosts, average concurrent sessions, RD Gateway topology, licensing model.
- Show automation depth: include specific TSSA jobs or NSH scripts, number of nodes automated, and any integrations with vulnerability scanners.
- Bring documentation samples (redacted): runbook snippets, architecture diagrams, or a short post‑mortem summary that demonstrates process maturity.
Conclusion
GovCIO’s Journeyman Windows System Administrator opening is an archetype of contemporary federal IT work: a demanding hybrid role that balances legacy Windows estate stewardship with virtualization, remote‑access security, and enterprise‑scale automation. Candidates need solid hands‑on skills across Windows Server and VMware, practical RDS deployment experience, and operational exposure to TrueSight or equivalent server automation frameworks — layered over the non‑negotiable baseline of DoD‑aligned certifications and clearance eligibility.For hiring managers, success will come from realistic scopes of work that reconcile Microsoft lifecycle realities, automation staffing, and the non‑trivial complexity of integrating RDS and patch orchestration into a STIG‑driven environment. For candidates, the path to being competitive is clear: document clear, verifiable operational wins, maintain required certifications and clearance status, and be ready to demonstrate both automation expertise and airtight documentation practices on day one.
Source: Dice https://www.dice.com/job-detail/5b3873bf-2771-4edc-8081-cc673a87bda4/



