Windows Administrator V

Summary

Join a company with Extraordinary People and Exceptional Performance! Chenega Professional Technical Services, LLC., a Chenega Professional Services company, is looking for an expert level Windows Administrator V, to perform enterprise identity and Active Directory (AD) migration to Entra ID and domain consolidation for a Federal Government customer.

A successful candidate must demonstrate expert level knowledge and experience in planning and executing AD to Entra ID migrations and consolidation activities and provide expert technical operations and maintenance (O&M) for the supported environment. 

Responsibilities

Work in coordination with the Project Manager and stakeholder to perform enterprise directory services, migration wave planning and communications, application owner engagement and compatibility testing, cutover execution with next-day support, and foundational operations & maintenance (O&M) of supported Windows-based services.

Perform AD to Entra ID technical migration and identity management

• Configure Entra ID (Azure AD) identity synchronization and validate directory health as required to support migration.
• Deploy automation pipelines; execute pilot migrations (~200 test users) prior to full-scale cutover.
• Conduct controlled nightly batches Monday–Thursday (≤150 users per night) with pre/post validation.
• Implement Kerberos/SSO.
• Perform workstation/domain re-joins.
• Design and Execute PowerShell automation.
• Provide Tier 3 escalation for permissions, Access Control List (ACL) remediation, Kerberos/SSO issues, and workstation/domain re-joins.
• Perform PowerShell automation for bulk updates and monitoring.
• Execute identity cutovers and deliver next-day support to resolve authentication, profile, and application access issues including PIV certificate login troubleshooting.
• Monitor event/system logs and performance; maintain OS and software patching baselines (WSUS or equivalent).
• Assist in infrastructure planning, design, and implementation; develop project plans for transition, administration, and ongoing operations.
• Prepare authoritative runbooks for Tier 1 and Tier2 helpdesk support.

Perform Foundational O&M

• Performance monitoring
• OS patching
• Backup/restore
• Configuration Management and Change Control
• Disaster Recovery testing
• Documentation and Training
• Daily status updates shall be provided before 12:00 PM MT, with urgent items escalated to PDA within one hour of identification.

1. Other duties as assigned

Qualifications

• A Bachelor’s Degree in a technology field
• 12 years of experience designing, configuring, and supporting Microsoft Windows system environments
• Expertise with Active Directory, Active Directory Federated Services, and Azure AD and Entra ID
• Kerberos/SSO
• PowerShell automation
• Large Enterprise experience
• Strict Change Control

Desirable Qualifications:

• Microsoft Certified: Windows Server Administrator Associate
• Microsoft Certified: Identity and Access Administrator Associate (SC-300)
• Azure Administrator Associate (AZ-104)
• Experience with DNS, DCHP
• Experience with ACL
• Experience with Group Policy, AGPM
• Experience with SCCM
• Experience with SCOM
• Experience with WSUS

Knowledge, Skills and Abilities:

• Authorized to work in the U.S. without sponsorship
• Must be able to pass the Public Trust Government background investigation
• Strong communication skills (both written and oral)
• Strong troubleshooting skills
• Ability to work closely with a small team
• Ability to work in a high stress environment

Teleworking Permitted?
Yes
Teleworking Details
100% remote, onsite travel as required
Estimated Salary/Wage
Up to USD $50.00/Hr.

Work in coordination with the Project Manager and stakeholder to perform enterprise directory services, migration wave planning and communications, application owner engagement and compatibility testing, cutover execution with next-day support, and foundational operations & maintenance (O&M) of supported Windows-based services.

Perform AD to Entra ID technical migration and identity management

• Configure Entra ID (Azure AD) identity synchronization and validate directory health as required to support migration.
• Deploy automation pipelines; execute pilot migrations (~200 test users) prior to full-scale cutover.
• Conduct controlled nightly batches Monday–Thursday (≤150 users per night) with pre/post validation.
• Implement Kerberos/SSO.
• Perform workstation/domain re-joins.
• Design and Execute PowerShell automation.
• Provide Tier 3 escalation for permissions, Access Control List (ACL) remediation, Kerberos/SSO issues, and workstation/domain re-joins.
• Perform PowerShell automation for bulk updates and monitoring.
• Execute identity cutovers and deliver next-day support to resolve authentication, profile, and application access issues including PIV certificate login troubleshooting.
• Monitor event/system logs and performance; maintain OS and software patching baselines (WSUS or equivalent).
• Assist in infrastructure planning, design, and implementation; develop project plans for transition, administration, and ongoing operations.
• Prepare authoritative runbooks for Tier 1 and Tier2 helpdesk support.

Perform Foundational O&M

• Performance monitoring
• OS patching
• Backup/restore
• Configuration Management and Change Control
• Disaster Recovery testing
• Documentation and Training
• Daily status updates shall be provided before 12:00 PM MT, with urgent items escalated to PDA within one hour of identification.

1. Other duties as assigned

• A Bachelor’s Degree in a technology field
• 12 years of experience designing, configuring, and supporting Microsoft Windows system environments
• Expertise with Active Directory, Active Directory Federated Services, and Azure AD and Entra ID
• Kerberos/SSO
• PowerShell automation
• Large Enterprise experience
• Strict Change Control

Desirable Qualifications:

• Microsoft Certified: Windows Server Administrator Associate
• Microsoft Certified: Identity and Access Administrator Associate (SC-300)
• Azure Administrator Associate (AZ-104)
• Experience with DNS, DCHP
• Experience with ACL
• Experience with Group Policy, AGPM
• Experience with SCCM
• Experience with SCOM
• Experience with WSUS

Knowledge, Skills and Abilities:

• Authorized to work in the U.S. without sponsorship
• Must be able to pass the Public Trust Government background investigation
• Strong communication skills (both written and oral)
• Strong troubleshooting skills
• Ability to work closely with a small team
• Ability to work in a high stress environment