Senior IT Technician (L2)

About the Role

Safebox Technology is a Managed IT Services provider based in Naples, Florida. We support established businesses across Southwest Florida: construction, medical, legal, manufacturing, and professional services with a focus on ownership, responsiveness, and accountability.

We are looking for a Senior IT Technician (L2) who can operate independently, take full ownership of client issues, and work directly with end users and business leadership in a fast-moving environment.

This is not a ticket-queue role. You will own problems end-to-end: From initial troubleshooting through resolution, communication, and documentation across multiple client environments. Priorities shift, issues do not always resolve on a schedule, and we expect you to stay engaged until the work is done and communicated properly.

What You Will Be Responsible For

• Own and resolve support tickets from start to finish across multiple client environments
• Troubleshoot issues across endpoints, networks, Microsoft 365, and business applications
• Work directly with end users and client leadership and communicate clearly with both
• Support remote and onsite requests depending on client needs
• Maintain accurate, timely documentation of work performed and resolutions
• Identify recurring issues and contribute to long-term fixes, not just quick resolutions
• Collaborate with the team when needed, but operate independently day-to-day
• Participate in client onboardings, installations, and environment improvements

Core Technical Capabilities

• Strong troubleshooting across Windows environments (Windows 10/11)
• Microsoft 365 user management, Exchange, basic tenant troubleshooting
• Networking fundamentals: DNS, DHCP, routing, VPNs, firewall basics
• End-user device support: Laptops, desktops, printers, mobile devices
• Proficient with remote support tools
• Active Directory and identity/access management basics

Additional Experience – strong plus:

• Windows Server administration
• Azure / Entra exposure
• Backup and recovery systems
• Firewall troubleshooting (SonicWall, UniFi, Fortinet)
• QuickBooks or line-of-business application support
• macOS troubleshooting

What We Expect From You

• You take ownership, you do not pass tickets without context or follow-through
• You manage multiple priorities without constant oversight
• You communicate clearly with technical and non-technical users alike
• You are comfortable working in environments that are not always perfectly documented
• You focus on solving problems, not just closing tickets
• You are accountable for your work and your outcomes
• Occasional after-hours or urgent support may be required. We do not abuse this, but it happens
• Before you call it a day your tickets are up to date.
• You understand documentation as you go is part of the job.

Qualifications

• Minimum 3 years of hands-on IT support experience
• MSP experience strongly preferred
• Strong troubleshooting ability across systems, networks, and applications
• Professional, client-facing communication skills
• Understanding of security best practices and data protection fundamentals
• Valid Florida driver's license and clean driving record
• Ability to lift and move standard IT equipment; occasional team lifts for heavier items
• You are a team player and you enjoy a fast paced and growing environment

This role is based in Naples, FL. You will split time between our office and client sites across Southwest Florida. A reliable, presentable vehicle is required for field visits.

What We Offer

• Competitive salary: 55K to 65K
• Health benefits (Health, Dental, Vision, Life)
• Paid time off and company holidays
• Being part of an exciting startup
• Direct access to leadership, you will not be lost in a large org
• Real ownership of your work across a diverse client base
• A clear path to grow into senior technical or client-facing leadership roles

Pay: $55,000.00 - $65,000.00 per year

Benefits:

• Dental insurance
• Employee discount
• Health insurance
• Life insurance
• Paid time off
• Vision insurance

Experience:

• Hands-on L2 IT: 3 years (Required)

Location:

• Naples, FL 34116 (Preferred)

Ability to Commute:

• Naples, FL 34116 (Required)

Work Location: In person