Helpdesk Support Specialist II

Helpdesk Support Specialist – Level 2 At Senior Star, technology plays an important role in helping our communities deliver exceptional experiences to residents, families, and associates every day. We are seeking a Helpdesk Support Specialist – Level 2 who brings strong technical troubleshooting skills, a service-minded attitude, and a desire to continue growing within Information Technology. Reporting directly to the Director of Information Technology, this role serves as the escalation point for more advanced technical support issues while helping maintain the systems, devices, and infrastructure our communities rely on daily. This position also serves as a mentor and technical resource for the Level 1 Helpdesk Specialist. The ideal candidate is someone who enjoys problem-solving, takes ownership of issues, communicates professionally with non-technical users, and approaches support with patience and partnership. What You’ll Do Escalation & Technical Support Resolve escalated help desk tickets that exceed Level 1 support capabilities Troubleshoot intermediate to advanced hardware, software, and connectivity issues Support workstations, laptops, printers, mobile devices, and peripheral equipment across multiple community locations Provide timely updates and excellent customer service throughout the support process Document resolutions clearly within the ticketing system to help strengthen the team knowledge base Serve as a technical mentor and resource for the Level 1 Helpdesk Specialist Infrastructure & Systems Support Support on-premises infrastructure including file shares, print servers, and local network environments Perform Active Directory administration including user management, group policy troubleshooting, and organizational unit maintenance Configure, image, and deploy devices while maintaining asset inventory Assist with VPN connectivity, remote access troubleshooting, and endpoint maintenance Ensure operating systems, antivirus software, and applications remain updated and secure Microsoft 365 & Platform Support Support Microsoft 365 applications including Teams, Outlook, SharePoint, and OneDrive Assist with licensing, access management, and user troubleshooting within the Microsoft 365 environment Support operational platforms including Yardi, WelcomeHome, Dayforce, and PointClickCare Escalate complex issues appropriately while helping maintain uptime and operational continuity Cybersecurity & Compliance Apply foundational cybersecurity best practices in daily support activities Help reinforce MFA enrollment, password policies, and secure computing practices Recognize and escalate suspicious activity, phishing attempts, or potential security concerns Support HIPAA-sensitive environments with professionalism and confidentiality Continue developing cybersecurity knowledge and technical skills through ongoing learning What We’re Looking For Minimum 3–5 years of experience in an IT support role, with at least 1–2 years handling escalated or Tier 2 issues High school diploma or equivalent required; Associate’s degree in IT or related field preferred CompTIA A+ certification required or actively in progress; CompTIA Network+ or Security+ preferred or actively pursued Solid hands-on experience with Windows OS, Microsoft 365, and on-premises hardware troubleshooting and repair Experience with Active Directory user and computer management in a domain environment Foundational understanding of cybersecurity concepts, including phishing, endpoint security, MFA, and password best practices Familiarity with help desk ticketing systems and ITSM processes for managing and documenting escalated tickets Ability to interact professionally with staff at all levels and across all community locations while communicating technical information clearly Demonstrated growth mindset — self-motivated to learn new technologies, pursue certifications, and take on expanded responsibilities over time Positive, dependable, and flexible individual who can adapt to a changing environment and occasionally support after-hours issues Confidential treatment of all information regarding the community, business, or residents Requires physically lifting and moving equipment short distances Why Senior Star? At Senior Star, we believe support roles make a direct impact on the daily experience of our residents and associates. Our IT team plays a critical role in keeping communities connected, supported, and operating smoothly. This is an opportunity to join a collaborative environment where your technical skills, professionalism, and service mindset truly matter. If you are looking for meaningful work, growth opportunities, and a team-focused culture, we’d love to hear from you. #INDSSM