L2 Helpdesk Technician
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Summary
Second-tier helpdesk technician at an IT services company supporting US-based clients from Chile: you own escalated tickets end-to-end, remediate remotely via Datto RMM and Autotask, administer Microsoft 365/Entra ID and Intune-managed endpoints, and triage security alerts on a fixed shift starting 2 PM CST.
We’re looking for a L2 Helpdesk Technician. You'll be the second tier of our service desk: the escalation point for issues L1 can't resolve, the hands on remote infrastructure via our RMM platform, and a frontline checkpoint for security and compliance. This is not a security analyst role, but in our environment, every technician is expected to recognize when a request is out of policy, out of compliance, or out of pattern, and route it accordingly rather than just "making it work."
This role supports clients based in US in real time. The shift tracks 2pm onwards CST.
What You’ll Do
- Own escalated tickets end-to-end: troubleshoot, resolve, document, and close with clear client communication at every step.
- Work daily in our RMM and PSA platforms (Datto RMM, Autotask) — remote remediation, scripted fixes, patch and agent health, monitoring response.
- Administer Microsoft 365 and Entra ID: user lifecycle, Exchange Online, SharePoint/OneDrive permissions, Conditional Access basics, Intune-managed endpoints.
- Support endpoints in a zero-trust application control environment (ThreatLocker): evaluate elevation and application approval requests, distinguish legitimate business need from policy bypass, and escalate exceptions through the proper channel.
- Recognize and flag out-of-compliance requests — local admin asks, unapproved software, data handling that conflicts with client compliance frameworks — rather than fulfilling them quietly
- Respond to alerts from our security stack (EDR/MDR, email security, identity threat detection) at the triage level: gather context, contain where runbooks allow, escalate cleanly
- Write documentation other technicians can actually follow: ticket notes, KB articles, client-facing summaries
- Hand off cleanly to US-based team members at the end of your shift
What We’re Looking For
- 2+ years in an MSP or multi-client IT support environment, with at least 1 year at an L2/escalation level.
- Strong working knowledge of Windows 10/11 administration, Microsoft 365 / Entra ID, Active Directory, DNS, DHCP, and core networking (VLANs, VPN, firewall concepts).
- Hands-on experience with an RMM/PSA toolset (Datto RMM and Autotask preferred; ConnectWise, NinjaOne, or similar acceptable)
- A genuine working understanding of security concepts: least privilege, application allowlisting, phishing and identity attack patterns, why compliance frameworks restrict what they restrict
- Exceptional written and spoken English. You will communicate directly with US clients daily. This is a hard requirement and will be assessed live during interviews.
- Demonstrated reliability on a fixed late schedule. Punctuality at 2 PM (CST) is non-negotiable.
Remote/Early-Shift Requirements
- Dedicated, quiet home workspace for early-shift hours
- Reliable fibre internet (50 Mbps+) with mobile failover.
Benefits
- Fun team activities every month to build strong bonds.
- We're located in a great area, with plenty to enjoy nearby (El Golf, Las Condes).
- Snacks and drinks are always stocked in the office.
- Weekly team lunches to recharge and connect.
- You’ll work closely with high-caliber US-based companies.
- Comprehensive health and dental insurance to keep you covered.
- Wellness activities reimbursement.