Support Desk Technician Tier 2

All potential candidates should read through the following details of this job with care before making an application.

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
• 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.
• 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
• Call-To-Action
• If you're ready to make an impact and be part of a passionate team that values innovation and customer service, we invite you to apply today! Join us at Proper Sky, where your expertise will shine.

Job Type : Full-time

Pay : $58,000.00 - $75,000.00 per year

Benefits :
• 401(k)
• 401(k) matching
• Dental insurance
• Employee assistance program
• Health insurance
• Paid time off
• Vision insurance

Work Location : In person