IT Systems Engineer; L2 | MSP or relative IT req'd

Position: IT Systems Engineer (L2) | 2 yr MSP or relative IT experience req'd
Location: Freeport

IT Systems Engineer (Level
2)

Check all associated application documentation thoroughly before clicking on the apply button at the bottom of this description.

* Proactive Data – Destin / Freeport, FL (Hybrid: Remote + Onsite as needed)
* Proactive Data is a growing managed IT services provider based in Northwest Florida. We’re looking for a
* Level 2 Systems Engineer
* who enjoys solving real technical problems, taking ownership of escalated issues, and working directly with clients in a professional, low-drama environment.

This role is ideal for someone who has moved beyond basic help desk work and is ready to operate with more autonomy and responsibility.

What You’ll Do

* Handle
* escalated support tickets
* from Level 1 technicians

* Troubleshoot and resolve issues involving:

* Windows 10/11 workstations

* Microsoft 365 (Exchange, Teams, One Drive)

* Active Directory, DNS/DHCP, Group Policy

* VPNs, networking, and connectivity issues

* Provide
* remote support
* and occasional
* onsite support
* when needed

* Own tickets end-to-end: troubleshoot, communicate, document, and close

* Assist with small to mid-size projects such as:

* Workstation rollouts

* Server or cloud migrations

* Firewall and network upgrades

* Document work clearly so issues don’t repeat

* Communicate professionally with non-technical users and set expectations clearly

* Identify recurring issues and recommend long-term fixes, not just quick patches

What We’re Looking For

* 2+ years of IT support experience (MSP experience strongly preferred)

* Strong Windows and Microsoft 365 troubleshooting skills

* Working knowledge of:

* Active Directory and user management

* Basic networking (LAN/WAN, Wi-Fi, VPN)

* Comfortable managing multiple tickets and priorities

* Good communication skills — you can explain technical issues without jargon

* Willingness to ask for help when needed and help others when you can

Nice to Have (Not Required)

* Experience with firewalls, servers, or virtualization

* Familiarity with RMM or PSA tools

* IT certifications (CompTIA, Microsoft, etc.)

Compensation & Benefits

* * Starting salary: $55,000+*, depending on experience

* No sales quotas or commission pressure

_(Hardware sales commission exists but is not a core part of compensation)_

* Health benefits (note: no traditional group health insurance)

* CWO and wellness-related benefits

* Paid time off (up front in full after 90 days)

* Company-provided polos and professional tools

* Stable work environment focused on quality, not burnout

Why Proactive Data

* Small team where your work actually matters

* Clear expectations and minimal bureaucracy

* Opportunity to grow into senior technical or leadership roles

* Local clients, real relationships, and practical IT work

Job Type: Full-time

Pay: $50,000.00 - $65,000.00 per year

Benefits:

* Employee discount

* Flexible schedule

* Life insurance

* Paid time off

Application Question(s):

* In the last 18 months, have you independently resolved escalated tickets from a Level 1 technician?

* Do your currently have any IT certifications?

* Have you administered Active Directory beyond password resets (e.g., groups, permissions, OUs, access issues)?

* Have you diagnosed and resolved DHCP, IP addressing, or subnetting issues in a business network?

* Have you troubleshot business VPN connectivity using logs or diagnostic tools? xrlwcon

* Have you participated in small to mid sized IT projects where you owned deliverables and documentation?

Education:

* High school or equivalent (Required)

Experience:

* Active Directory: 2 years (Required)

* Windows Server OS: 1 year (Required)

* Office 365 Setup or Email Migration to 365: 2 years (Required)

Work Location:

In person