Systems Support Specialist (MSP)

About Safebox Technology Safebox Technology is a fast-growing Managed IT Services Provider supporting businesses across Southwest Florida. We work with companies in construction, healthcare, manufacturing, and professional services. This is not a repetitive helpdesk role. Our technicians work directly inside client environments solving real-world problems across desktops, networks, Microsoft 365, servers, WiFi, security, onboarding, and infrastructure projects. One day may involve troubleshooting a Microsoft 365 issue remotely. The next could involve deploying a UniFi network, replacing a firewall, onboarding a new client, or handling onsite support during a business outage. If you like variety, autonomy, and solving problems independently, you will do well here. About The Role We are looking for a strong Systems Support Specialist who can operate independently, communicate professionally with clients, and handle a wide variety of technical situations without constant direction. This role is ideal for someone with prior MSP or broad IT support experience who enjoys hands-on work, learning quickly, and taking ownership of problems from start to finish. You do not need to know everything but you do need to be resourceful, adaptable, accountable, and capable of figuring things out. This position is for local candidates in the Southwest Florida area only. Daily onsite and client-facing work is required. What You'll Be Doing Troubleshoot and resolve support requests across desktops, Microsoft 365, networking, servers, and business applications Perform onsite and remote technical support for client environments Deploy and support workstations, firewalls, wireless systems, switches, and related infrastructure Participate in client onboarding projects and environment improvements Handle escalations and work through issues independently before escalating further Maintain accurate ticket notes, documentation, and time entries Identify recurring issues and recommend long-term improvements Represent Safebox professionally during all client interactions Adapt quickly to changing priorities and field situations throughout the day

Technical Experience We're Looking For:

Strong Working Knowledge Of:

Windows 10/11 Microsoft 365 administration and troubleshooting Active Directory and user management Networking fundamentals (DNS, DHCP, VPN, WiFi, firewalls) Remote support and troubleshooting End-user hardware and printer support

Experience With Any Of The Following Is A Strong Plus:

Windows Server Azure / Entra SonicWall, Fortinet, or UniFi Backup and disaster recovery systems QuickBooks or line-of-business applications macOS support Prior MSP experience Working within MSP ticketing, documentation, and RMM platforms What Makes Someone Successful Here You take ownership of problems instead of waiting for instructions You stay calm under pressure and adapt quickly You communicate well with both clients and teammates You can manage multiple priorities without constant supervision You enjoy variety and hands-on technical work You are organized, dependable, and accountable You leave environments better than you found them This role is NOT a fit for someone looking for a highly structured corporate IT environment or repetitive helpdesk-only work. Requirements 3+ years of hands-on IT support experience Prior MSP or field support experience preferred Strong troubleshooting ability across systems and networks Professional communication and client-facing skills Valid driver's license and reliable transportation Ability to lift and move standard IT equipment when needed Must currently reside within reasonable commuting distance of Naples, FL. Compensation & Benefits $60,000

• $75,000 depending on experience Health, Dental, Vision, and Life Insurance Paid Time Off (10 days) + Holidays (8 days) Mileage reimbursement Ongoing technical growth and exposure to real-world environments Direct access to leadership and decision-making Opportunity to grow rapidly within a fast-moving

MSP Pay:

$60,000.00

• $75,000.

00 per year

Benefits:

Dental insurance Health insurance Life insurance Paid time off Vision insurance

Work Location:

In person Systems Support Specialist (MSP) Naples, FL 34116 $60,000

• $75,000 a year
• Full-time $60,000
• $75,000 a year
• Full-time About Safebox Technology Safebox Technology is a fast-growing Managed IT Services Provider supporting businesses across Southwest Florida.

We work with companies in construction, healthcare, manufacturing, and professional services. This is not a repetitive helpdesk role. Our technicians work directly inside client environments solving real-world problems across desktops, networks, Microsoft 365, servers, WiFi, security, onboarding, and infrastructure projects. One day may involve troubleshooting a Microsoft 365 issue remotely. The next could involve deploying a UniFi network, replacing a firewall, onboarding a new client, or handling onsite support during a business outage. If you like variety, autonomy, and solving problems independently, you will do well here. About The Role We are looking for a strong Systems Support Specialist who can operate independently, communicate professionally with clients, and handle a wide variety of technical situations without constant direction. This role is ideal for someone with prior MSP or broad IT support experience who enjoys hands-on work, learning quickly, and taking ownership of problems from start to finish. You do not need to know everything but you do need to be resourceful, adaptable, accountable, and capable of figuring things out. This position is for local candidates in the Southwest Florida area only. Daily onsite and client-facing work is required. What You'll Be Doing Troubleshoot and resolve support requests across desktops, Microsoft 365, networking, servers, and business applications Perform onsite and remote technical support for client environments Deploy and support workstations, firewalls, wireless systems, switches, and related infrastructure Participate in client onboarding projects and environment improvements Handle escalations and work through issues independently before escalating further Maintain accurate ticket notes, documentation, and time entries Identify recurring issues and recommend long-term improvements Represent Safebox professionally during all client interactions Adapt quickly to changing priorities and field situations throughout the day

Technical Experience We're Looking For:

Strong Working Knowledge Of:

Windows 10/11 Microsoft 365 administration and troubleshooting Active Directory and user management Networking fundamentals (DNS, DHCP, VPN, WiFi, firewalls) Remote support and troubleshooting End-user hardware and printer support

Experience With Any Of The Following Is A Strong Plus:

Windows Server Azure / Entra SonicWall, Fortinet, or UniFi Backup and disaster recovery systems QuickBooks or line-of-business applications macOS support Prior MSP experience Working within MSP ticketing, documentation, and RMM platforms What Makes Someone Successful Here You take ownership of problems instead of waiting for instructions You stay calm under pressure and adapt quickly You communicate well with both clients and teammates You can manage multiple priorities without constant supervision You enjoy variety and hands-on technical work You are organized, dependable, and accountable You leave environments better than you found them This role is NOT a fit for someone looking for a highly structured corporate IT environment or repetitive helpdesk-only work. Requirements 3+ years of hands-on IT support experience Prior MSP or field support experience preferred Strong troubleshooting ability across systems and networks Professional communication and client-facing skills Valid driver's license and reliable transportation Ability to lift and move standard IT equipment when needed Must currently reside within reasonable commuting distance of Naples, FL. Compensation & Benefits $60,000

• $75,000 depending on experience Health, Dental, Vision, and Life Insurance Paid Time Off (10 days) + Holidays (8 days) Mileage reimbursement Ongoing technical growth and exposure to real-world environments Direct access to leadership and decision-making Opportunity to grow rapidly within a fast-moving

MSP Pay:

$60,000.00

• $75,000.

00 per year

Benefits:

Dental insurance Health insurance Life insurance Paid time off Vision insurance

Work Location:

In person