IT Help Desk Technician (Junior) - Hybrid, Ocala FL

We're hiring a Junior IT Help Desk Technician to serve as the first line of defense and support for our clients. You'll start by learning our internal systems, tools, and processes, and shadowing team members on client site visits to understand each customer's environment. Once onboarded, you'll handle remote support tickets, work through alert queues, perform system maintenance, and help continually improve the IT support and cybersecurity experience we deliver to every client. Expect regular dispatch to client sites for hands-on support, onboarding, and project work.

This is a hybrid role - primarily work-from-home with regular onsite dispatch across our service area.

What You'll Do

• Serve as the first point of contact for client support requests via phone, email, and ticketing system
• Triage, troubleshoot, and resolve Tier 1 issues remotely; escalate appropriately when needed
• Work through system alerts, monitoring notifications, and proactive maintenance tickets
• Shadow senior technicians on client visits during onboarding to learn each client's environment
• Travel onsite to client locations for support calls, hardware installs, and IT projects
• Assist with IT implementation projects (workstation deployments, network installs, migrations, etc.)
• Document work clearly in our PSA/ticketing system and contribute to client knowledge bases
• Help identify opportunities to improve client cybersecurity posture and overall IT experience
• Maintain professional, courteous communication with clients at all times

Technical Environment You'll Work In

• Endpoints: Windows and macOS computers; Android and Apple mobile devices and tablets
• Cloud/Productivity: Microsoft 365 for identity, file sharing, email, and Teams collaboration
• Networking: Wired and wireless networks, VLANs, routing, firewall policies, and VPNs
• Servers: Some clients still run local Windows Server environments with on-prem Active Directory
• Additional services we support: Business phone systems, security camera systems, AI for business solutions, cloud solutions, and keyless access control systems

• 1-3 years of IT support, help desk, or MSP experience
• Solid working knowledge of Windows and macOS troubleshooting
• Basic networking skills - able to troubleshoot wired/wireless issues, understand VLANs, routing, firewalls, and VPNs at a working level
• Comfortable supporting Microsoft 365 end-user issues (email, OneDrive, Teams, SharePoint)
• Professional written and verbal communication skills
• Strong customer service mindset - patient, courteous, and clear with non-technical users
• Valid Florida driver's license and reliable personal transportation
• Must live in Marion County or an immediately adjacent county (Alachua, Lake, Citrus, or Levy). Applicants outside this area will not be considered.
• Ability to pass a background check

Preferred Experience (Not Required)

• Prior experience working at an MSP (Managed Service Provider)
• Microsoft 365 admin experience: Exchange, SharePoint, Teams, OneDrive, and Entra ID (Azure AD)
• Local Active Directory management on Windows Server
• Experience with PSA/RMM platforms (SuperOps, ConnectWise, Datto, NinjaOne, etc.)
• Familiarity with backup platforms, endpoint security, and email security tools
• Exposure to VoIP phone systems, IP camera systems, or access control platforms

Preferred Certifications (Not Required)

• CompTIA A+
• CompTIA Network+
• CompTIA Security+
• Microsoft MS-900 (Microsoft 365 Fundamentals)
• Microsoft MD-102 (Endpoint Administrator)
• Microsoft AZ-900 (Azure Fundamentals)

• Flexible schedule
• Paid time off

Simply IT is a veteran-owned managed IT and cybersecurity services provider based in Ocala, Florida. We support small and mid-sized businesses across Marion and surrounding counties, with a focus on medical, dental, legal, accounting, veterinary, trades, and church clients. Our mission is to deliver enterprise-grade IT and cybersecurity to businesses that don't have an in-house IT department - with the personal touch of a local partner.