IT Service Desk Technician - Level 2 at CIO… · Tampa

About CIO Tech

CIO Technology Solutions is a Tampa-based Managed Services Provider focused on responsive support, strong communication, and operational consistency.

We hire people that take ownership. People that follow through. People that document what they touched and communicate clearly with customers and teammates.

This is not an environment where tickets disappear into queues for days or where someone else cleans up the details afterward.

We promote from within and give people room to grow if they can handle responsibility.

Role

We are looking for a Level 2 Service Technician to handle escalated support issues across Microsoft 365, servers, networking, firewalls, and line-of-business systems across multiple client environments.

This role is a mix of remote support, onsite work, troubleshooting, customer communication, and operational discipline. You’ll work closely with Level 1 technicians, Professional Services, and Account Management to keep client environments stable and issues moving.

What you’ll do

• Handle escalated support tickets and work issues through resolution
• Troubleshoot desktops, servers, Microsoft 365, networking, VPN, and firewall issues
• Support Windows Server environments, Active Directory, Entra ID, DNS, DHCP, Group Policy
• Administer Microsoft 365 including Exchange Online, Teams, SharePoint, and OneDrive
• Support and troubleshoot VLANs, switches, wireless, VPN connectivity, and basic routing
• Configure and support firewall changes and security policies within defined standards
• Maintain clear ticket notes, documentation, and time entries in ConnectWise Manage
• Document client environments, recurring fixes, and procedures in IT Glue
• Communicate directly with end users, vendors, and internal teams
• Assist with onboarding, workstation deployments, and technical projects when needed
• Participate in the on-call rotation and escalation process
• Help mentor and support Level 1 technicians

What matters in this role

• You finish what you start
• You communicate early when something is blocked or going sideways
• You don’t close tickets without verifying the issue is actually resolved
• You can explain technical issues to non-technical users without sounding condescending
• You manage your workload without needing constant follow-up
• You keep documentation and time entries current instead of trying to remember everything later

Requirements

• 3+ years in an MSP or multi-client IT support environment
• Strong troubleshooting skills across Windows, Microsoft 365, networking, and endpoint support
• Experience with Active Directory, Entra ID, Group Policy, DNS, DHCP, VPNs
• Practical firewall and network troubleshooting experience
• Experience supporting Windows Server environments
• Ability to prioritize and manage multiple active issues at once
• Reliable documentation habits and same-day time entry
• Valid driver’s license for occasional onsite work

Nice to have

• ConnectWise Manage, NinjaOne, IT Glue, Liongard, AutoElevate
• Proxmox, VMware, or Hyper-V
• Veeam or other backup platforms
• Huntress, SentinelOne, DNSFilter, or similar security platforms
• Basic PowerShell scripting and automation experience

Benefits

• 15 days PTO in your first year plus paid holidays
• IRA with a company match
• Medical, dental, vision, life, and ancillary insurance options
• Company events, team lunches, referral bonuses
• Paid volunteer time
• Business casual environment