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

IT Systems Engineer (Level 2)

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*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, OneDrive) * 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? xhqgsiq * 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