Senior IT Support Desk Technician (Tier 2) – Hybrid Role

Proper Sky - Managed IT Services; United States; Hybrid; USD 70,000 - 100,000; Full time

Benefits offered by this job

Medical, dental, vision & long-term‑di

SIMPLE IRA + matching

Unlimited snacks & weekly lunches

Regular company outings

Career development opportunities

Volunteer opportunities

Job summary

Proper Sky - Managed IT Services is seeking a proactive Support Desk Technician (Tier 2) to join our MSP team. You’ll resolve complex IT issues, mentor junior staff, and contribute to documentation and process improvements, with a focus on Microsoft 365, networking, and server administration.

Ideal candidates bring 5+ years of hands-on IT support, strong communication skills, and a client-first mindset. This hybrid role reports to our Abington, PA headquarters and offers growth opportunities

Qualifications

• 5+ years of hands-on IT support experience in a helpdesk/MSP environment.
• Certifications such as CompTIA Network+/Security+, Microsoft AZ-104/Azure Administrator, and Cisco CCNA are a plus.
• ITIL Foundation 4 or higher is preferred.
• Strong knowledge of Microsoft 365 suite and related services; proficient in Windows OS and server networking.

Responsibilities

• Troubleshoot and resolve complex end-user issues across desktops, laptops, printers, and mobile devices.
• Triage tickets by urgency and impact to client organizations; provide remote and on-site support as needed.
• Mentor Tier 1/Junior technicians and contribute to SOPs and documentation.
• Collaborate with project teams on migrations, upgrades, and deployments.
• Maintain accurate documentation in ConnectWise and knowledge bases.

Skills

MS 365

Azure AD

Exchange Online

SharePoint

Teams

Intune

Active Directory

Networking

Windows Troubleshooting

ConnectWise

Tools

ConnectWise Manage

ConnectWise Automate

ScreenConnect

Job description

Proper Sky - Managed IT Services is seeking a proactive Support Desk Technician (Tier 2) to join our MSP team. You’ll resolve complex IT issues, mentor junior staff, and contribute to documentation and process improvements, with a focus on Microsoft 365, networking, and server administration.

Ideal candidates bring 5+ years of hands-on IT support, strong communication skills, and a client-first mindset. This hybrid role reports to our Abington, PA headquarters and offers growth opportunities