Why Work for Proper Sky?
At Proper Sky, your work will make an impact from day one. As a small and agile team, we offer meaningful responsibility early on and continuous opportunities to grow, no matter your role. Every day brings fresh challenges and the chance to build new skills in a collaborative, fast-paced environment.
You’ll work closely with leadership and key stakeholders, gaining visibility and influence across the organization. Our team is made up of dedicated, mission-driven professionals who care deeply about delivering exceptional results for our clients and supporting one another.
We’re committed to your development and success. We provide leadership and professional growth opportunities through industry-leading programs like IT Nation, along with other third-party training and support. At Proper Sky, you’ll learn our systems, improve them, and bring value every day.
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:
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Assess Urgency and Impact of each problem to ensure the appropriate resolution timeline is achieved.
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Triage all assigned tickets in a manner that matches the urgency and impact to our clients organization.
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Diagnose and resolve complex end-user issues related to desktops, laptops, printers, and mobile devices
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Troubleshoot server and network-related issues (DNS, DHCP, VPN, Active Directory, etc.
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Troubleshoot escalated support tickets from a Tier 1 technician
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Identify root causes and implement permanent fixes
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Provide remote and occasional on-site support for critical issues
Problem Escalation Support:
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Provide technical assistance and mentorship to Tier 1 and junior technicians
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Escalate issues to Tier 3 or engineering teams when necessary, with detailed documentation
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Identify root causes of escalated issues and ensure SOP’s are documented to ensure next-level support can resolve the issue if it repeats.
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Collaborate with project teams on migrations, upgrades, and deployments
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Participate in team standups and knowledge-sharing sessions
Project Execution:
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Execute defined scopes of work based on engineering or service manager assignments
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Provide status updates on assigned project tasks and collaborate closely with Project Managers, Engineers, and Service Managers
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Identify risks or blockers during project execution and escalate appropriately
Documentation & Continuous Improvement:
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Maintain accurate and up-to-date documentation in ConnectWise, Hudu and the knowledge base
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Contribute to internal process improvements and standard operating procedures (SOPs)
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Flag recurring issues and propose solutions to reduce repeat incidents
Client Engagement:
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Provide professional and empathetic communication to clients via phone, email, and ticketing systems
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Ensure timely and accurate updates to clients on issue status and resolutions
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Maintain customer satisfaction by meeting or exceeding SLAs and expectations for each problem you are navigating
Qualifications
Education & Technical Experience:
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5+ years of relevant hands-on IT support experience in a helpdesk, MSP, or technical support environment
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Certifications such as CompTIA Network+/Security+, Microsoft AZ-104, Azure Administrator Associate and Cisco CCNA a plus
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ITIL Foundation 4 or higher
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Strong knowledge of Microsoft 365, Azure AD, Exchange Online, SharePoint, Teams, and Intune
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Proficient in troubleshooting Windows OS, servers, networking issues (DNS, DHCP, VPN, VLANs, firewalls)
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Familiarity with backup systems, EDR platforms, and RMM tools
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Experience with ConnectWise Manage, Automate, ScreenConnect, or similar tools preferred
Soft Skills:
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Strong verbal and written communication skills
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Ability to manage multiple tasks and prioritize in a fast-paced environment
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Self-starter with a continuous learning mindset
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Team player with mentoring capabilities
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Highly organized, detail-oriented, and customer-service driven
Work Schedule:
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The Support Technician role covers the 8am-5pm EST shift.
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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:
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This role is a hybrid role and reports locally to Proper Sky’s headquarters in Abington, PA for all scheduled shifts.
Compensation & Benefits:
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Compensation is commensurate with experience
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Listed salary ranges apply to U.S. workers only
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Medical, dental, vision & long-term disability insurances
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Generous sick, vacation, and paid time off
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SIMPLE IRA + match
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Career development opportunities
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Unlimited snacks & weekly paid lunches
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Regular company outings
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Community volunteer opportunities
The pay range for this role is:
60,000 - 80,000 USD per year(Hybrid (United States))
