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IT Systems Support Specialist II
New Kingstown, PAMarch 23rd, 2026
IT Systems Support Specialist IIK2 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 devicesTroubleshoot escalated issues involving Active Directory, Microsoft Entra ID, DNS, DHCP, VPN, and network connectivitySupport Microsoft 365 services including Exchange Online, Teams, SharePoint, and OneDriveAdminister user accounts, permissions, and licensing in Active Directory and Entra IDManage endpoint configuration and compliance through Microsoft Intune (MDM)Support Conditional Access policies and multi-factor authenticationParticipate in Windows 11 upgrade planning and deployment initiativesMonitor and remediate systems using NinjaOne RMMDeploy and maintain PowerShell-based automation (Windows PowerShell 5.1 compatible)Assist with patch management, endpoint security hardening, and vulnerability remediationSupport backup and disaster recovery solutionsMaintain accurate documentation of system changes and ticket resolutionsMentor Tier I support staff by reviewing escalations, reinforcing troubleshooting methodology, and promoting documentation standardsParticipate in after-hours upgrades, troubleshooting, and on-call rotation as neededOther duties as assignedThe Ideal Candidate Will Have:3-5+ years of systems support experienceStrong experience with:Windows 10/11 administrationMicrosoft 365 administrationActive Directory & Entra IDNetworking fundamentals (DNS, DHCP, TCP/IP, VPN)Experience with Microsoft Intune and endpoint managementWorking knowledge of Conditional Access and identity security best practicesExperience with Hyper-V, VMware, or other virtualization platformsExperience with backup and disaster recovery systemsFamiliarity with PowerShell scriptingCertifications such as CompTIA A+, Network+, Security+, Microsoft 365 Certified, or Azure Fundamentals (AZ-900) preferredStrong documentation discipline and customer service focusAbility to lift and move objects weighing up to 50 lbs
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