Helpdesk Support Specialist II

Benefits and culture

Senior Star offers a role where your work directly impacts residents and associates. The IT team keeps communities connected, supported, and operating smoothly. Join a collaborative environment where your technical skills, professionalism, and service mindset matter. This position provides meaningful work, opportunities to grow, and a team-focused culture.

Responsibilities

• 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
• 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
• 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
• 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

Requirements

• 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

Technologies

• Windows OS
• Microsoft 365
• Active Directory
• Yardi
• WelcomeHome
• Dayforce
• PointClickCare
• Teams
• Outlook
• SharePoint
• OneDrive
• VPN
• MFA