Senior Desktop Support Specialist - Windows & MDT Expert

Bridgehead IT; San Antonio (TX); Hybrid; USD 70,000 - 90,000; Full time

Job summary

Bridgehead IT is seeking a Desktop Support Specialist III to act as a senior technical resource, delivering advanced troubleshooting and mentoring to junior staff. The role focuses on resolving complex issues, handling escalations, and supporting desktop infrastructure deployments, with on-call and after-hours support as needed.

Responsibilities include leading workstation deployments, building system images, remote and on-site support, and cross-functional collaboration with Network, Server,

Qualifications

• 5–7+ years in desktop or technical support.
• Strong Windows 10/11 and Microsoft 365 expertise.
• Proficient in Active Directory, DNS/DHCP, and Group Policy.
• MD-102 or AZ-104 certifications preferred.

Responsibilities

• Provide expert-level desktop support for hardware, software, OS, and peripherals.
• Serve as escalation point for junior Desktop Support Specialists I & II.
• Troubleshoot Windows, Office 365, VPN, and endpoint security issues.
• Lead and participate in workstation deployments and refreshes.
• Build and maintain system images and deployment processes.
• Support client environments remotely and on-site with minimal downtime.
• Manage tickets with thorough documentation and time entries.
• Assist in documenting procedures and knowledge base content.
• Coordinate cross-functional tickets with Network, Server, Cloud, and Security teams.
• Assist in onboarding and offboarding and in provisioning equipment.
• Support endpoint compliance, patch management, and antivirus/EDR.

Skills

Desktop support

Troubleshooting

Customer service

Windows 10/11

Microsoft 365

Mentoring

Documentation

Education

MD-102

AZ-104

Tools

MDT

Autopilot

Job description

Description

Company Overview:

Bridgehead IT is a leading provider of innovative technology solutions dedicated to guaranteed outcomes that bring peace of mind and improve its clients’ bottom line. With a commitment to operational excellence and client satisfaction, Bridgehead IT delivers tailored solutions that drive business success.

Position Summary:

The Desktop Support Specialist III acts as a senior technical resource within the support team, delivering advanced troubleshooting and mentoring to junior staff. This role is responsible for resolving complex technical issues, handling escalated tickets, and supporting desktop infrastructure deployments. The position operates primarily within a ticketing system and includes participation in an on-call rotation and after-hours support as needed.

Duties/Responsibilities:

• Provide expert-level desktop support for issues involving hardware, software, operating systems, and peripheral equipment.
• Serve as a technical escalation point for Desktop Support Specialists I and II.
• Support advanced troubleshooting of issues related to Microsoft Windows, Office 365, remote access (VPN), and endpoint security tools.
• Lead and participate in workstation deployments, refreshes, and small-scale implementations.
• Build and maintain system images and deployment processes using company-approved tools.
• Maintain and support client environments both remotely and on-site, ensuring minimal disruption to end users.
• Manage service tickets within the ticketing system, ensuring complete documentation, accurate time entries, and timely resolution.
• Assist in developing and improving documentation, procedures, and knowledge base content.
• Coordinate with other teams (Network, Server, Cloud, Security) on cross-functional tickets or projects.
• Participate in onboarding and offboarding processes, including provisioning, recovery, and configuration of equipment.
• Support and enforce endpoint compliance policies, patch management, and antivirus/EDR effectiveness.
• Participate in an on-call rotation and respond to after-hours issues when necessary.
• Perform additional tasks as assigned.

Education and Experience:

• 5–7+ years of experience in desktop or technical support roles, preferably within an enterprise or MSP environment.
• Strong expertise in Windows 10/11, Microsoft 365, and desktop management tools.
• Working knowledge of Active Directory, Group Policy, DNS/DHCP, and basic networking.
• Proficiency with remote support tools and ticketing systems.
• Experience with deployment tools such as MDT, Autopilot, or equivalent.
• Excellent troubleshooting, communication, and customer service skills.
• Ability to lift and move equipment (up to 50 lbs) and travel to client sites when required.
• Industry certifications such as Microsoft MD-102 or Microsoft AZ-104 are preferred.
• Demonstrated ability to lead by example, support junior team members, and take ownership of complex issues.

Why Join Bridgehead IT?

• Serve as a trusted advisor for a diverse portfolio of SMB and Major Accounts.
• Influence technology strategy and business outcomes.
• Work alongside highly skilled engineers, architects, and technology leaders.
• Gain exposure to a wide range of industries and technologies.
• Enjoy a high-impact role with significant visibility and growth opportunities.
• Be part of a team that values ownership, innovation, accountability, and exceptional client service.

Disclaimer:

The duties and responsibilities described in this job description are not a comprehensive list and additional tasks may be assigned to the employee from time to time. This job description in no way states or implies that these are the only duties to be performed by the employee(s) in this position. Employees will be required to follow any other job-related instructions and to perform any other job-related duties requested by any person authorized to give instructions or assignments. All duties and responsibilities are essential functions and requirements and are subject to possible modification to reasonably accommodate individuals with disabilities. To perform this job successfully, the employees will possess the skills, aptitudes, and abilities to perform each duty proficiently. The requirements listed in this document are the minimum levels of knowledge, skills, or abilities.