L2 IT Helpdesk Engineer

Live Oak IT Partners is hiring a Systems Support Technician (L2 IT Helpdesk Engineer) in hybrid mode out of San Antonio, TX 78213. This role helps keep client environments running smoothly as tickets move beyond L1 triage, with direct collaboration alongside Senior Systems Engineers and the Projects team.

You’ll focus on system-level troubleshooting, proactive monitoring, and documentation that keeps teams aligned. If you enjoy owning escalations end to end, partnering with vendors when needed, and helping L1 technicians level up, this position is built for that.

What you’ll do

• Troubleshoot system-level issues across Active Directory, Microsoft Entra ID (Azure AD), Intune, Microsoft 365, Google Workspace, UniFi, and related technologies.
• Manage software installations, configuration changes, and patching across Windows and macOS endpoints.
• Respond to RMM alerts and maintain endpoint monitoring, including the on-site monitoring devices placed at client offices.
• Keep client runbooks current in IT Glue/Hudu, document fixes, and log clear, accurate notes in Halo PSA.
• Collaborate with Senior Systems Engineers and Projects on infrastructure work and major incidents.
• Mentor L1 technicians by answering questions, reviewing escalations, and supporting growth as they level up.
• Escalate to L3 or vendors when an issue is outside L2 scope, ensuring troubleshooting steps are already documented.

What you bring

• 4 years in IT support, with at least 1 year handling escalations or system administration (MSP experience strongly preferred).
• Hands-on administration of Microsoft 365 and Entra ID: users, licensing, groups, MFA, and conditional access basics.
• Working knowledge of on-premises Active Directory, Exchange, and Group Policy.
• Experience supporting both Windows and macOS in a business environment.
• Comfort using a ticketing system and an RMM platform, with a habit of documenting as you work.
• Comfort working with third-party vendors on behalf of clients.
• Clear, friendly communication with non-technical users by phone and in writing.
• A valid driver’s license and reliable transportation for occasional client site visits.

Tools and technologies

Active Directory, Microsoft Entra ID (Azure AD), Intune, Microsoft 365, Google Workspace, UniFi, Windows, macOS, RMM, IT Glue, Hudu, Halo PSA, Exchange, Group Policy.

Benefits

• 401(k) matching
• Health insurance, dental insurance, and vision insurance
• Life insurance
• Paid time off
• Parental leave
• Referral program
• Retirement plan
• Tuition reimbursement

Preferred experience

• Experience with the stack: Halo PSA, IT Glue/Hudu, NinjaOne, Addigy, Intune, Huntress, and UniFi networking.
• Google Workspace and Microsoft 365 administration.
• Networking fundamentals: DNS, DHCP, VLANs, firewalls, and site-to-site as well as client VPNs.
• Experience mentoring or training junior technicians.

Compensation: $60,000.00 - $85,000.00 per year

Work location: Hybrid remote in San Antonio, TX 78213