It Helpdesk Associate Jobs in Silver Spring, MD (NOW HIRING)

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 ID administration, 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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Responsibilities

• 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 ID / Active Directory environments, including user account provisioning, group policy adjustments, and identity lifecycle management, in coordination with IAM governance.
• Support macOS and iOS administration, including device enrollment, configuration profile deployment, FileVault management, and integration with enterprise authentication and compliance frameworks.
• Perform secure drive sanitization and destruction using BitRaser or other approved tools, maintaining required documentation and certificates of destruction.
• Use approved hard drive cloning devices and software to support workstation deployments, refreshes, data migrations, and recovery operations.

Citizenship

U.S. citizens, or lawful permanent residents.

Required Qualifications

• Must be able to provide enterprise-level administration and support for macOS and Windows operating systems, including imaging, deployment, configuration management, and adherence to organizational security baselines.
• Experience utilizing and supporting endpoint management and automation platforms such as Ivanti, KACE, Microsoft Intune, and JAMF to deploy software, manage devices, enforce policies, and streamline routine tasks.

Knowledge, Skills & Abilities

• The ability to manage and troubleshoot identity and access management services, including Microsoft Entra ID/Active Directory, multi-factor authentication (MFA), role-based access controls, and AWS-integrated identity solutions.
• The ability to diagnose and resolve authentication, connectivity, and endpoint performance issues by analyzing system logs, Event Viewer data, macOS Console diagnostics, and other relevant monitoring tools.
• The ability to coordinate cross-team incident response activities by working closely with the Service Desk, Network Operations, and Cybersecurity teams to ensure timely investigation, escalation, and remediation of technical issues
• A strong understanding of advanced system administration including patch management, baseline configuration, automated imaging processes, and the ability to troubleshoot and improve endpoint deployment workflows.
• A strong understanding of cloud and hybrid environment management, with specific experience supporting AWS-hosted resources, identity services, and integrations between on-premises and cloud-based infrastructures.
• A strong understanding of Zero Trust security principles, ensuring all endpoint, user, and network interactions follow the organization's security, compliance, and configuration standards.
• Clear and effective communication, including the ability to document technical procedures, create user-friendly guides, and mentor Level I technicians to enhance overall Service Desk capability.
• Must have excellent customer service and problem-solving skills and the ability to prioritize tasks to meet tight deadlines while maintaining professionalism and responsiveness.

Education

• Bachelor's degree in information technology, Computer Science, or a closely related field.

Preferred Qualifications

• CompTIA Security+
• Microsoft Certified: Endpoint Administrator Associate (or equivalent)
• Apple Certified IT Professional
• AWS Certified Cloud Practitioner (or higher-level AWS certification)
• ITIL Foundation or equivalent certification in service management
• Certified SysOps Administrator - Associate

Compensation & Benefits[1][2]

• Wage Range: Negotiable
• General Benefits: Custom Software Systems, Inc. offers our employees a competitive benefits package that may include:

• Health insurance plans
• Health Savings Account (HSA)
• Dental
• Vision
• Long-term disability
• Short-term disability
• Basic term life insurance
• Supplemental term life insurance for employees, spouses, and dependents
• Simple IRA
• Parking/Commuting expense reimbursement
• Training/Education

[1] Compensation range must be coordinated with and approved by the CSS Chief Operating Officer (COO).

[2] Compensation & Benefits information is required for all Maryland Employers effective October 1, 2024.