Support Desk Technician Tier 2

About the role

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.

What you'll do

Technical Troubleshooting & Resolution:

• Assess Urgency and Impact of each problem to ensure the appropriate resolution timeline is achieved.
• Triage all assigned tickets in a manner that matches the urgency and impact to our clients 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 a Tier 1 technician
• Identify root causes and implement permanent fixes
• Provide remote and occasional on-site 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 the issue if it 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 the 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

Qualifications

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.

Compensation & Benefits:

• Compensation is commensurate with experience
• Listed salary ranges apply to U.S. workers only
• Medical, dental, vision & long-term disability insurances
• Generous sick, vacation, and paid time off
• SIMPLE IRA + match
• Career development opportunities
• Unlimited snacks & weekly paid lunches
• Regular company outings
• Community volunteer opportunities