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.

The pay range for this role is: 60,000 - 80,000 USD per year (Hybrid (United States))