THE ROLE
As our Tier 1 Help Desk Technician, you''re the first voice our partners reach when something isn''t working. You''ll own incoming tickets, work through the standard playbook to resolve what you can and escalate cleanly when a problem belongs higher up the bench. You''ll work from home most days and drive to client sites across the San Antonio metro when the work needs hands on it: swapping hardware, walking a user through a new setup, or helping a team get back up after an outage. You report to our Service Manager who will set you up with the tools, the partners, and the work. This is a foundational seat at Lone Cypress and the right place to start an MSP career.
WHAT YOU''LL DO
• Own incoming Tier 1 tickets across our partner base: password resets, account lockouts, Microsoft 365 issues, printer and peripheral problems, basic network connectivity, and standard desktop support.
• Document every ticket clearly in Autotask: what was reported, what you did, what resolved it, and what the partner needs to know.
• Keep our partner documentation accurate and current in IT Glue as you discover new information in the field.
• Drive to client sites across the San Antonio metro when work requires hands-on attention: new user setups, hardware swaps, on-site troubleshooting, and project support alongside senior engineers.
• Escalate cleanly when a ticket belongs with Tier 2 or a senior engineer, meaning the next person to pick it up knows exactly where you left off.
• Participate in our after-hours on-call rotation, taking your turn to keep partners covered outside business hours.
• Communicate with partners the way we expect plainspoken, honest about what''s happening, and respectful of their time.
WHAT YOU BRING
• One or more years of help desk, IT support, or comparable hands-on technical experience. Strong candidates with formal training and a clear pattern of self-taught work will also be considered.
• Working knowledge of Windows 10/11, Microsoft 365 (Exchange Online, Teams, SharePoint, OneDrive), Active Directory or Entra ID, and basic networking fundamentals (DNS, DHCP, IP addressing, common troubleshooting).
• Comfort working in a ticketing system and discipline about documenting your work as you go.
• Clear written and verbal communication. You can explain a technical problem to a non-technical user without making them feel small.
• Reliable transportation, a valid driver''s license, and an acceptable driving record. Driving to partner sites across the San Antonio area is a regular part of the work.
• Willingness to take your turn in the after-hours on-call rotation. When you work billable hours after hours you earn a commission from each hour worked.
• Preferred (not required): CompTIA A+, Network+, or Microsoft 365 Fundamentals; prior MSP experience; familiarity with Autotask PSA, IT Glue, or any RMM platform (Datto, Kaseya, NinjaOne, ConnectWise Automate).
OUR STACK
You''ll work daily with Autotask PSA for ticketing and time entry, IT Glue for partner documentation, our RMM for monitoring and remote support, and the Microsoft 365 admin center for most user and mailbox work. Prior experience with these specific tools is a plus, but we''ll train the right person on the platform. What we can''t train is judgment, work ethic, and how you treat people.
WHY LONE CYPRESS
• A steady team, not a churn shop. Our techs stay because the work is interesting and the people around them are good.
• A real path forward. Tier 1 is the start, not the ceiling. We invest in certifications, training time, and a clear progression to Tier 2 and beyond.
• Partners, not accounts. We treat our partners like peers, and we expect our team to be treated the same way.
• South Texas roots. We''re based in San Antonio, we hire here, and our work is grown-up and specific, not flashy.
• Compensation and benefits package, paid time off, on-call compensation, mileage reimbursement for partner site visits, and a quality home-office setup and stipend for mobile phone & Internet for home office.
Never miss an opportunity! Create an alert based on the job you applied for.
