IT Support Desk Technician (Tier 2)

The Support Desk Technician (Tier 2) at Proper Sky is a key member of our service delivery team, responsible for resolving complex technical issues, supporting escalations, and ensuring a seamless IT experience for our clients. This role requires a strong technical foundation in Microsoft 365, networking, and server administration, paired with exceptional communication skills and a client-first mindset. You’ll troubleshoot advanced support tickets, mentor junior technicians, and contribute to documentation and process improvements. The ideal candidate is a proactive, solutions-driven professional who thrives in a fast-paced MSP environment and is committed to service excellence.

Primary Duties:

Technical Troubleshooting & Resolution:

• Assess Urgency and Impact of each problem to ensure appropriate resolution timeline is achieved.
• Triage all assigned tickets in manner that matches the urgency and impact to our clinets organization.
• Diagnose and resolve complex end-user issues related to desktops, laptops, printers, and mobile devices
• Troubleshoot server and network-related issues (DNS, DHCP, VPN, Active Directory, etc.)
• Troubleshoot escalated support tickets from Tier 1 technicians
• Identify root causes and implement permanent fixes
• Provide remote and occasional onsite support for critical issues

Problem Escalation Support:

• Provide technical assistance and mentorship to Tier 1 and junior technicians
• Escalate issues to Tier 3 or engineering teams when necessary, with detailed documentation
• Identify root causes of escalated issues and ensure SOP’s are documented to ensure next-level support can resolve if issue repeats.
• Collaborate with project teams on migrations, upgrades, and deployments
• Participate in team standups and knowledge-sharing sessions

Project Execution:

• Execute defined scopes of work based on engineering or service manager assignments
• Provide status updates on assigned project tasks and collaborate closely with Project Managers, Engineers, and Service Managers
• Identify risks or blockers during project execution and escalate appropriately

Documentation & Continuous Improvement:

• Maintain accurate and up-to-date documentation in ConnectWise, Hudu and knowledge base
• Contribute to internal process improvements and standard operating procedures (SOPs)
• Flag recurring issues and propose solutions to reduce repeat incidents

Client Engagement:

• Provide professional and empathetic communication to clients via phone, email, and ticketing systems
• Ensure timely and accurate updates to clients on issue status and resolutions
• Maintain customer satisfaction by meeting or exceeding SLAs and expectations for each problem you are navigating

Education & Technical Experience:

• 5+ years of relevant hands-on IT support experience in a helpdesk, MSP, or technical support environment
• Certifications such as CompTIA Network+/Security+, Microsoft AZ-104, Azure Administrator Associate and Cisco CCNA a plus
• ITIL Foundation 4 or higher
• Strong knowledge of Microsoft 365, Azure AD, Exchange Online, SharePoint, Teams, and Intune
• Proficient in troubleshooting Windows OS, servers, networking issues (DNS, DHCP, VPN, VLANs, firewalls)
• Familiarity with backup systems, EDR platforms, and RMM tools
• Experience with ConnectWise Manage, Automate, ScreenConnect, or similar tools preferred

Soft Skills:

• Strong verbal and written communication skills
• Ability to manage multiple tasks and prioritize in a fast-paced environment
• Self-starter with a continuous learning mindset
• Team player with mentoring capabilities
• Highly organized, detail-oriented, and customer-service driven

Work Schedule:

• The Support Technician role covers the 8am-5pm EST shift.
• The position is subject to covering a rotating “On-Call” shift from 5pm-10pm (Weekdays) and 8am-5pm (Weekends/Holidays) to respond to after-hours emergency requests.

Work Location:

• This role is a hybrid role and reports locally to Proper Sky’s headquarters in Abington, PA for all scheduled shifts.

Pay: $55,000.00 - $75,000.00 per year, * 401(k) matching

• Dental insurance
• Employee assistance program
• Health insurance
• Life insurance
• Paid time off
• Professional development assistance
• Retirement plan
• Vision insurance

Proper Sky, Inc. has provided managed information technology (IT) services since 2006, including cybersecurity, cloud, backup and disaster recovery, and project services. The team focuses on practical solutions, responsive support, and strong customer partnerships.