Help Desk Technician Level II
Lone Cypress Technology \| San Antonio, TX \| Hybrid \| $55K–$60K
Includes: $200 monthly health insurance stipend
About Us
Lone Cypress Technology is a growing MSP in San Antonio delivering enterprise\-grade IT with a personal touch. We’re built on ownership, reliability, and real teamwork. If you love solving problems for people and want to be part of something that’s scaling fast, keep reading.
The Role
This is a hybrid position : 50% remote, 50% on\-site at client locations across San Antonio. You’ll handle escalated support tickets, manage M365 environments, troubleshoot servers and networking, and serve as the go\-to tech for our clients. This is not entry\-level. We need someone with real MSP experience who can own the client relationship.
What You’ll Do
- Resolve escalated hardware, software, and connectivity issues via phone, remote session, and on\-site visits
- Administer Microsoft 365 (Exchange, Teams, SharePoint, Intune, Entra ID)
- Support Windows Server environments (AD, Group Policy, DNS, DHCP)
- Troubleshoot networking at an intermediate level (routers, switches, firewalls, VLANs, VPNs)
- Manage tickets and documentation in Autotask PSA, Datto RMM, and IT Glue
- Monitor and respond to security alerts (Barracuda XDR, SentinelOne MDR)
- Travel to client sites in the San Antonio metro area as needed
- Participate in on\-call rotation for after\-hours support
- Expert\-level: Windows 10/11, macOS, M365 admin (Exchange, Teams, Intune, Entra ID, MFA, Conditional Access)
- Intermediate: Windows Server (AD, GPO, DNS, DHCP), networking (TCP/IP, VLANs, VPN, firewalls)
- Experience with PSA/RMM tools (Autotask, Datto RMM or equivalent)
- Strong documentation habits and clear communication skills
- Valid driver’s license and reliable transportation
- Must pass an FBI background check (we support local government clients)
- CompTIA A\+, Network\+, Security\+ or Microsoft certs (MS\-900, MD\-102, AZ\-900\)
- Experience with Kaseya 365Ops suite, Barracuda XDR, or SentinelOne MDR
- 401(k) matching
- Dental insurance
- Paid time off
- Professional development assistance
- Vision insurance
Requirements
* 5\+ years in an MSP environment : this is a firm requirement
Nice to Have
We value hands\-on MSP experience over formal education and certifications.
Pay: $55,000\.00 \- $60,000\.00 per year
Benefits:
Work Location: Hybrid remote in San Antonio, TX 78216