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

• 3–5 years of IT support experience with exposure to escalated or Tier 2 issues
• Strong troubleshooting skills within Windows and Microsoft 365 environments
• Experience with Active Directory and basic networking concepts
• Excellent communication and customer service skills
• A positive, dependable, and adaptable mindset
• Someone who enjoys learning, growing, and taking on increasing responsibility
• Ability to explain technical concepts clearly to non-technical associates

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.

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