IT Help Desk Specialist (Windows, macOS & Endpoint Management) 

Position Title: IT Help Desk Specialist (Windows, macOS & Endpoint Management) 

Location: Washington, DC (On-site) with occasional travel within Northern Virginia 

Client: Federal Government Programs 

Employment Type: Full-Time | Contract 

Work Authorization: Candidates must be authorized to work in the United States. Candidates must be eligible to successfully complete required background screening and security requirements prior to onboarding. 

How to Apply 

📩 Email your resume: careers@wintrio.com 

Job Summary 

WINTrio LLC is seeking an experienced IT Help Desk Specialist to provide advanced technical support for Federal enterprise IT environments. This position is responsible for deploying, maintaining, troubleshooting, and supporting Windows, macOS, and mobile computing platforms while delivering exceptional customer service and ensuring compliance with enterprise security standards. 

The successful candidate will work closely with Service Desk, Network Operations, Cloud Services, Engineering, and Cybersecurity teams to support endpoint management, identity services, workstation lifecycle management, and secure enterprise computing environments. This role requires strong technical expertise in endpoint administration, Microsoft technologies, macOS management, and enterprise IT operations. 

Job Responsibilities 

• Deploy, configure, and support Windows desktops, macOS systems, laptops, and mobile devices. 

• Install, configure, troubleshoot, and maintain computer hardware, operating systems, software, peripherals, and firmware. 

• Configure and manage enterprise mobile devices, including iOS and Android platforms, authentication, Multi-Factor Authentication (MFA), and secure remote access. 

• Deploy software, operating system images, and configuration baselines using Microsoft Intune, JAMF, Ivanti Endpoint Manager (EPM), KACE, or equivalent endpoint management platforms. 

• Diagnose and resolve hardware, software, authentication, networking, operating system, and endpoint performance issues. 

• Perform workstation imaging, deployment, software installation, upgrades, patch management, and device refresh activities. 

• Administer Microsoft Entra ID (Azure AD) and Active Directory, including user provisioning, group management, password resets, and identity lifecycle support. 

• Support enterprise macOS environments, including device enrollment, configuration profiles, FileVault encryption, and authentication integration. 

• Analyze Windows Event Viewer and macOS Console logs to identify root causes and resolve technical issues. 

• Develop and maintain Standard Operating Procedures (SOPs), technical documentation, and knowledge base articles. 

• Mentor junior technical support staff and assist with escalated technical issues. 

• Coordinate with Service Desk, Network Operations, Cloud Services, Engineering, and Cybersecurity teams to ensure timely incident resolution. 

• Monitor service tickets, communicate status updates, and maintain excellent customer service throughout the incident lifecycle. 

• Replace defective hardware, maintain IT asset inventory records, and document configuration changes. 

• Identify recurring technical issues and recommend process improvements to improve operational efficiency. 

• Apply cybersecurity best practices, including Zero Trust principles, secure credential management, encryption, and endpoint security controls. 

• Perform secure hard drive sanitization, workstation cloning, data migration, backup, and recovery activities. 

Required Qualifications 

• Bachelor’s degree in Information Technology, Computer Science, or a related technical discipline; or equivalent professional experience. 

• Experience supporting enterprise Windows and macOS environments. 

• Experience administering endpoint management platforms such as Microsoft Intune, JAMF, Ivanti Endpoint Manager (EPM), KACE, or equivalent solutions. 

• Experience administering Microsoft Entra ID (Azure AD) and Active Directory. 

• Experience supporting Multi-Factor Authentication (MFA) and Identity & Access Management (IAM). 

• Experience troubleshooting endpoint hardware, operating systems, software, networking, authentication, and connectivity issues. 

• Experience performing workstation deployment, imaging, software installation, configuration management, and patch management. 

• Understanding of Zero Trust Architecture and enterprise endpoint security best practices. 

• Experience supporting cloud or hybrid enterprise IT environments. 

• Strong analytical, troubleshooting, documentation, communication, and customer service skills. 

• Ability to work effectively in a collaborative, fast-paced enterprise IT environment. 

Technical Areas 

Endpoint Management 

• Windows Administration 

• macOS Administration 

• Mobile Device Management (MDM) 

• Endpoint Deployment 

• Workstation Imaging 

• Patch Management 

• Device Lifecycle Management 

Identity & Access Management 

• Microsoft Entra ID (Azure AD) 

• Active Directory 

• Multi-Factor Authentication (MFA) 

• Identity Lifecycle Management 

• Authentication Services 

Enterprise Support 

• Desktop Support 

• Laptop Support 

• Mobile Device Support 

• Technical Troubleshooting 

• Hardware & Software Support 

• IT Asset Management 

Security & Compliance 

• Zero Trust Principles 

• Endpoint Security 

• Secure Credential Management 

• Encryption 

• Secure Device Configuration 

• Data Protection 

Tools & Platforms 

Endpoint Management 

• Microsoft Intune 

• JAMF 

• Ivanti Endpoint Manager (EPM) 

• KACE 

Microsoft Technologies 

• Windows 10/11 

• Microsoft Entra ID (Azure AD) 

• Active Directory 

• Microsoft 365 

Operating Systems 

• Windows 

• macOS 

• iOS 

• Android 

Enterprise Support Tools 

• Windows Event Viewer 

• macOS Console 

• Remote Support Tools 

• Ticketing Systems 

Cloud & Collaboration 

• Microsoft Azure 

• Microsoft Teams 

• Microsoft Outlook 

Preferred Certifications 

• CompTIA Security+ 

• Microsoft Certified: Endpoint Administrator Associate 

• Apple Certified IT Professional 

• AWS Certified Cloud Practitioner 

• AWS Certified SysOps Administrator – Associate 

• ITIL Foundation 

Preferred Qualifications 

• Experience supporting Federal Government agencies or regulated enterprise environments. 

• Experience supporting cloud-based or hybrid infrastructure environments. 

• Experience working with enterprise endpoint security and compliance initiatives. 

• Experience supporting large-scale workstation deployments and endpoint lifecycle management. 

• Experience working within ITIL-based service management environments. 

Work Environment 

• Full-time position. 

• On-site in Washington, DC. 

• Occasional support may be required at alternate locations within Northern Virginia. 

• Standard business hours Monday through Friday. 

• Occasional after-hours or emergency support may be required. 

WINTrio Benefits 

• Healthcare (Medical, Dental, and Vision) 

• Flexible Spending Account (FSA) and Health Savings Account (HSA) 

• 401(k) and Retirement Savings Plan 

• Annual Bonus and Profit Sharing Opportunities 

• Paid Time Off (PTO) and Vacation 

• Employee Assistance Program (EAP) 

• Life, Personal, and Voluntary Disability Insurance 

Growth Opportunities 

This position offers opportunities to work with modern endpoint management platforms, cloud technologies, enterprise cybersecurity, identity and access management, and Federal IT modernization initiatives. At WINTrio, we foster an employee-driven culture that values innovation, collaboration, technical excellence, and continuous professional development. 

Equal Opportunity Employer 

WINTrio LLC is an Equal Opportunity/Affirmative Action Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, gender identity, sexual orientation, national origin, age, disability, protected veteran status, or any other characteristic protected by applicable federal, state, or local law.