Help Desk Technician Tier 2

Asteroid IT is seeking a full-time Help Desk Technician (Tier 2) to manage client support tickets end to end across multiple environments. In a hybrid remote setup based in the Phoenix metro, you will troubleshoot a wide range of Windows, Microsoft 365, identity, and networking issues, while also assisting with infrastructure and compliance-focused project work when tickets are not the immediate priority.

Key Responsibilities

• Own incoming client support tickets from intake through resolution across multiple client environments.
• Triaging and prioritizing issues by severity and SLA, while communicating progress and status directly with clients.
• Troubleshoot and resolve issues independently across Windows Server 2022-2025, Windows 10/11, Microsoft 365, and network connectivity.
• Administer Microsoft 365 and Entra ID, including accounts, licensing, permissions, MFA, and mail flow.
• Support and maintain onsite Windows Servers at client locations.
• Administer and respond to alerts in Huntress, and manage Sophos firewall and email security policies.
• Troubleshoot network issues involving HP switches, Ubiquiti equipment, VLANs, DNS, DHCP, and VPNs.
• Use ConnectWise Automate for monitoring, patching, and remote management across client environments.
• Maintain accurate ticket notes in ConnectWise Manage and documentation in IT Glue.
• Escalate problems with clear notes when deeper analysis or design work is required.
• Assist the Project Engineer on infrastructure initiatives, including server builds, upgrades, migrations, network deployments, firewall configuration, and security tooling rollouts.
• Take on defined project work pieces as assigned.
• Support client onboarding and offboarding, including workstation deployments and account provisioning.
• Assist with compliance remediation work such as encryption, access controls, audit logging, and documentation for clients with CMMC, HIPAA, and FTC Safeguards obligations.
• Build and maintain documentation and technical standards in IT Glue.

Required Qualifications

• 2+ years of hands-on experience in a multi-client MSP environment.
• Hands-on experience supporting and maintaining on-premises Windows Server, including Active Directory, Group Policy, DNS, and DHCP.
• Strong Microsoft 365 and Windows administration skills.
• Ability to work issues through to resolution independently, with good judgment on when escalation is necessary.
• Solid understanding of networking fundamentals including DNS, DHCP, VLANs, VPNs, and switch configuration.
• Working knowledge of ticketing systems, SLAs, and MSP workflows.
• Clear, professional communication with end users and client stakeholders, including non-technical audiences.
• Strong organization, reliability, and a documentation-focused approach.
• Genuine interest in continued growth in technical support.
• Working proficiency with, or demonstrated ability to quickly ramp up on: ConnectWise Manage, ConnectWise Automate, IT Glue, Huntress, Sophos firewalls and email protection, HP switches, and Ubiquiti.
• Reliable high-speed internet and a dedicated, quiet home workspace.
• U.S. citizenship is required due to Department of Defense contract requirements for personnel accessing client environments or facilities.
• Must be located in the Phoenix metro area.
• Valid driver’s license and reliable transportation for onsite client visits.
• Willingness to undergo a background check in accordance with applicable law.
• Willingness to take a pre-employment drug test in accordance with applicable law.

Technologies You Will Use

• Windows Server 2022-2025, Windows 10/11, Microsoft 365, Entra ID
• Huntress, Sophos firewalls, Sophos email security policies
• HP switches, Ubiquiti, VLANs, DNS, DHCP, VPNs
• ConnectWise Automate, ConnectWise Manage, IT Glue
• Active Directory, Group Policy, Hyper-V, Proxmox, VMware
• ThreatLocker, CrowdStrike, Wazuh, Duo, Fortigate
• CMMC, NIST 800-171, HIPAA, FTC Safeguards Rule, IRS Publication 4557
• CompTIA Security+, CompTIA Network+, Microsoft certifications, Sophos certifications
• SOC 2, CIS Controls, AI tools

Schedule and Work Environment

• Full-time position, Monday through Friday, 8:00 AM to 5:00 PM.
• Hybrid role: primarily remote with in-person support at client sites in the Phoenix metro; occasional out-of-state travel may be required.
• No sales or quoting responsibilities.

Compensation

USD 55,000 - 65,000 per year.

Benefits

• Paid time off: 40 hours per year for the first two years of continuous employment, increasing to 80 hours after two years (accrual begins after a 60-day waiting period).
• Paid sick time.
• Eight paid holidays per year: six fixed and two floating.
• Company-provided laptop and equipment.
• Vendor certification training.

Project Support Focus

• Assist with infrastructure work including server builds, upgrades, migrations, network deployments, firewall configuration, and security tooling rollouts.
• Support assigned portions of project work as directed.
• Help with client onboarding and offboarding, including workstation deployments and account provisioning.
• Support compliance remediation work involving encryption, access controls, audit logging, and documentation for CMMC, HIPAA, and FTC Safeguards obligations.
• Maintain documentation and technical standards in IT Glue.

Bonus Skills (Desired but Not Required)

• Server virtualization experience (Hyper-V, Proxmox, or VMware).
• Experience with ThreatLocker, CrowdStrike, Wazuh, Duo, or Fortigate.
• Server, domain, or email migration experience.
• Backup solution deployment and management.
• Experience supporting compliance-driven environments (CMMC, NIST 800-171, HIPAA, IRS Publication 4557, FTC Safeguards Rule).
• Familiarity with CPA, healthcare, legal, or other regulated industry clients.
• CompTIA Security+, Network+, Microsoft certifications, or Sophos certifications.
• Exposure to SOC 2 or CIS Controls frameworks.
• Experience using AI tools to work faster or troubleshoot more effectively.