IT Systems Support Specialist II at K2 Insurance Services, LLC – Harrisburg, Pennsylvania

IT Systems Support Specialist II

K2 Insurance Services is seeking a full-time IT Systems Support Specialist II to join its IT team. This position is available in Harrisburg, PA, primarily onsite with occasional remote flexibility.

K2 Insurance, through its affiliated insurance companies and agencies, continues to expand its product offerings and distribution by developing new insurance programs and increasing the number and geographic diversity of its marketing, sales, underwriting, and support staff.

The IT Systems Support Specialist II provides Tier 2 technical support and plays a key role in maintaining secure, stable, and compliant IT systems. This position supports Microsoft enterprise technologies, escalated infrastructure issues, automation initiatives, and mentors Tier I staff.

K2 Insurance offers the opportunity to join an established company in growth mode. Our pay and benefits program includes competitive salary; bonus plan; medical, dental, and vision insurance; paid time-off in year of hire; and 401(k) with employer match.

Pay range: $30.00–$32.00 hourly, USD (based on experience)

IT Systems Support Specialist II Responsibilities Include:

• Provide advanced (Tier 2) on-site and remote technical support for Windows 10/11 endpoints, Microsoft 365, printers, peripherals, and mobile devices
• Troubleshoot escalated issues involving Active Directory, Microsoft Entra ID, DNS, DHCP, VPN, and network connectivity
• Support Microsoft 365 services including Exchange Online, Teams, SharePoint, and OneDrive
• Administer user accounts, permissions, and licensing in Active Directory and Entra ID
• Manage endpoint configuration and compliance through Microsoft Intune (MDM)
• Support Conditional Access policies and multi-factor authentication
• Participate in Windows 11 upgrade planning and deployment initiatives
• Monitor and remediate systems using NinjaOne RMM
• Deploy and maintain PowerShell-based automation (Windows PowerShell 5.1 compatible)
• Assist with patch management, endpoint security hardening, and vulnerability remediation
• Support backup and disaster recovery solutions
• Maintain accurate documentation of system changes and ticket resolutions
• Mentor Tier I support staff by reviewing escalations, reinforcing troubleshooting methodology, and promoting documentation standards
• Participate in after-hours upgrades, troubleshooting, and on-call rotation as needed
• Other duties as assigned

The Ideal Candidate Will Have:

• 3–5+ years of systems support experience
• Strong experience with:
  • Windows 10/11 administration
  • Microsoft 365 administration
  • Active Directory & Entra ID
  • Networking fundamentals (DNS, DHCP, TCP/IP, VPN)
• Experience with Microsoft Intune and endpoint management
• Working knowledge of Conditional Access and identity security best practices
• Experience with Hyper-V, VMware, or other virtualization platforms
• Experience with backup and disaster recovery systems
• Familiarity with PowerShell scripting
• Certifications such as CompTIA A+, Network+, Security+, Microsoft 365 Certified, or Azure Fundamentals (AZ-900) preferred
• Strong documentation discipline and customer service focus
• Ability to lift and move objects weighing up to 50 lbs