Job Title

Job DescriptionROLE OVERVIEW We are seeking a highly skilled, execution-focused Tactical Engineer to accelerate remediation of technology debt across our Microsoft and Azure environments. This contractor will work directly with the VP, Systems Engineering, and partner teams to deliver rapid, high-impact improvements. The ideal candidate is a hands-on expert who thrives in fast-paced, transformation-driven environments and can deliver results with minimal oversight. Key Priorities & Responsibilities ¥ Decommission Active Directory Certificate Services o Plan and execute the safe retirement of legacy AD CS infrastructure. o Ensure all dependencies are identified and remediated. ¥ Implement and Migrate to Entra Domain Services o Architect and lead migration from legacy Active Directory to Microsoft Entra Domain Services. o Support hybrid scenarios and ensure seamless integration with existing workloads. ¥ Implement Intune Client Broker for Autopatch Devices o Deploy and configure Intune client broker to enable Windows Autopatch for eligible devices. o Optimize device enrollment and compliance policies. ¥ Plan for Group Policy Objects (GPO) in Entra Domain Services o Design and implement GPO strategies compatible with Entra Domain Services. o Migrate or refactor existing GPOs as needed. ¥ Migrate from Entra Connect Sync to Entra Cloud Sync o Lead migration planning and execution from legacy Entra Connect Sync to Entra Cloud Sync. o Ensure minimal disruption and full data integrity. ¥ Enhance Windows AutoPilot o Improve and automate Windows AutoPilot provisioning and lifecycle management. o Troubleshoot and resolve deployment issues. ¥ General Tactical Engineering o Automate repetitive tasks using PowerShell and Intune scripts. o Collaborate with Cloud, Security, and Application teams to resolve incidents and implement changes. o Document all technical procedures, changes, and incidents for knowledge management. Performance Metrics ¥ Project Completion Rate: Timely remediation of prioritized tech debt items, including: o Decommissioning Active Directory Certificate Services. o Migration to Entra Domain Services and Entra Cloud Sync. o Implementation of Intune client broker for Autopatch devices. o Enhancement of Windows AutoPilot and GPO planning in Entra. ¥ Migration Success: Successful migration with minimal disruption and zero critical issues. ¥ Automation Impact: Number of manual processes replaced by automated workflows (e.g., PowerShell, Intune scripts). ¥ System Reliability: Reduction in incidents or outages related to legacy systems and improved compliance/security posture. ¥ Documentation Quality: Delivery of clear, comprehensive documentation for all technical changes and procedures. Expectations ¥ Tactical Execution: Deliver rapid, high-quality remediation of tech debt items with minimal oversight. ¥ Communication: Provide regular status updates, early flag risks, and collaborate effectively with cross-functional teams. ¥ Quality & Security: Ensure all migrations and implementations meet organizational security and compliance standards. ¥ Documentation: Maintain clear, concise documentation for all technical changes and procedures. ¥ Adaptability: Respond quickly to changing priorities and emerging issues. Work Structure ¥ Reporting: VP, System Engineer. ¥ Engagement Model: Contract-based, focused on deliverables rather than hours. ¥ Cadence: Weekly check-ins for progress review and reprioritization. ¥ Collaboration: Work closely with Cloud, Security, and Application teams; attend relevant project meetings. ¥ Tools: Use Microsoft Teams, SharePoint, and project management platforms for communication and tracking. ¥ Deliverables: Each tech debt item will have a defined scope, timeline, and acceptance criteria. Required Skills & Experience ¥ Proven experience in rapid remediation of tech debt in Microsoft/Azure environments. ¥ Deep expertise in Active Directory, Entra Domain Services, Intune, Windows Autopatch, GPO, and AutoPilot. ¥ Advanced PowerShell scripting and automation skills. ¥ Experience with migration projects and legacy system decommissioning. ¥ Strong troubleshooting and incident response capabilities. ¥ Excellent documentation and communication skills. ¥ Ability to work independently and deliver results on aggressive timelines. Success Metrics ¥ Number of legacy systems/services decommissioned. ¥ Successful migration to modern platforms (Entra, Intune, Cloud Sync). ¥ Reduction in manual processes and tech debt backlog. ¥ Improved reliability and automation of device management and provisioning