IT Help Desk Specialis

Custom Software Systems, Inc. (CSS) is seeking an experienced IT Help Desk Specialist to support our client in Washington, DC. This is an excellent opportunity for a customer-focused IT professional with strong Windows, macOS, and enterprise endpoint support experience to join a high-performing team supporting a secure federal environment. The ideal candidate will have expertise in desktop deployment, imaging, Active Directory/Entra , mobile device management, troubleshooting complex technical issues, and delivering exceptional end-user support.

If you're passionate about technology, enjoy solving challenging problems, and thrive in a collaborative, mission-driven environment, we'd love to hear from you.

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• Inspect computer equipment and prepare systems for deployment based on onboarding documentation and division-specific requirements, ensuring proper imaging, configuration, and inventory registration prior to delivery.
• Deploy and configure Windows desktops, macOS systems, and mobile devices following the imaging process, ensuring each device is properly inventoried, validated against security baselines, and ready for end-user delivery in accordance with division-specific requirements and IRM standards.
• Install, configure, troubleshoot, and maintain employee hardware, software, and peripheral components across Windows and macOS environments, including upgrades, patches, firmware updates, and approved security configurations to maintain compliance with Zero Trust and Defense-in-Depth standards.
• Register and configure mobile devices (iOS, Android) within enterprise mobile device management (MDM) platforms; provide users with training and troubleshooting on authentication, MFA, and secure remote connectivity.
• Load and verify software packages and configuration baselines through automated imaging and patching tools such as Ivanti EPM, KACE, or equivalent, ensuring accuracy and adherence to approved division templates.
• Execute system verification tests by entering administrative commands and monitoring log output to validate image integrity, patch levels, and compliance with endpoint security policies; confirm logs are being received in accordance with guidance from Sentinel, VSOC, and other monitoring platforms.
• Diagnose and resolve complex system issues, including multi-factor authentication failures, identity anomalies, network connectivity problems, and endpoint irregularities, applying independent judgment to identify root causes and implementing corrective actions while protecting sensitive data.
• Support Tier I personnel by enforcing best practices, creating and validating SOPs, reviewing escalations, and collaborating on issue resolution. Leverage JAMF and Microsoft Intune for endpoint automation and configuration management. Apply system administration expertise to analyze Windows Event Viewer and macOS Console logs, identify error patterns, and develop evidence-based solutions to prevent recurrence.
• Instruct users on the effective use of equipment, collaboration software, cloud services, and self-service resources; contribute to end-user documentation and knowledge base updates.
• Coordinate activities with the Service Desk, Network Operations, Cloud Services, and Cybersecurity teams to ensure timely issue resolution and alignment with IRM standards.
• Provide clear and timely communication on ticket status, updates, and resolutions through the official tracking system, voicemail, email, or direct user interaction in accordance with customer service performance metrics.
• Replace defective or obsolete hardware and software components, document all changes, and verify asset records in accordance with CBO asset management procedures.
• Identify and analyze recurring problem trends, develop mitigation strategies, and present findings and improvement recommendations to IRM management.
• Ensure rigorous application of information security and information assurance principles in all aspects of customer support, including encryption, data loss prevention, and secure credential handling.
• Administer Microsoft Entra  / Active Directory environments, including user account provisioning, group policy…