Desk Technician Tier 1

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.

The Support Desk Technician (Tier
1) at Proper Sky is the first point of contact for our clients’ IT support needs, delivering responsive, professional, and high‑quality assistance. This role focuses on resolving common technical issues, providing excellent customer service, and escalating more complex problems to higher‑tier technicians. The ideal candidate is a detail‑oriented problem solver with a passion for technology, a strong willingness to learn, and a client‑first mindset.

• Serve as the initial contact for incoming support requests via phone, email, and ticketing system.
• Assess urgency and impact of each request and ensure proper prioritization.
• Troubleshoot and resolve common end‑user issues involving desktops, laptops, printers, mobile devices, and basic network connectivity.
• Provide Microsoft 365 support, including Outlook, Teams, SharePoint, and One Drive.
• Perform basic account administration in Active Directory, Azure AD, and Microsoft 365.
• Document all work performed in the ticketing system accurately and thoroughly.

• Gather detailed information and troubleshooting steps before escalating issues to Tier 2 or Tier 3 technicians.
• Work closely with senior technicians to learn resolution processes for recurring issues.
• Follow established standard operating procedures (SOPs) for escalations and service delivery.

• Assist with basic project tasks under the direction of a Project Manager or senior engineers.
• Perform hardware setup and deployment (workstations, peripherals, and devices).
• Participate in migrations, upgrades, or other small‑scale technical initiatives as assigned.

• Maintain accurate and up‑to‑date documentation in Connect Wise, Hudu, and other platforms ensuring all tickets are up-to-date and resolutions are documented.
• Contribute to the internal knowledge base by documenting solutions for resolved issues.
• Identify opportunities to improve workflows, processes, or customer satisfaction.

• Deliver professional, clear, and empathetic communication to clients.
• Provide timely updates to clients regarding ticket progress and resolution timelines.
• Uphold service level agreements (SLAs) and maintain a high standard of customer service.

• 2–3 years of IT support or helpdesk experience, preferably in a Managed Services Provider (MSP) or technical support environment.
• Proven but basic knowledge of Microsoft 365, Windows OS, and common business applications.
• Demonstrated familiarity with Active Directory, Azure AD, and basic networking concepts (DNS, DHCP, VPN).
• Certifications such as CompTIA A+, Network+, Security+ are a plus.
• Basic understanding of troubleshooting Windows Desktop OS, Microsoft 365, networking issues (DNS, DHCP, and VPN).
• Experience with Connect Wise Manage, Automate, Screen Connect, or similar tools preferred.

• Strong verbal and written communication skills.
• Ability to follow instructions and escalate appropriately when needed.
• Eagerness to learn and grow technical skills in a fast‑paced environment.
• Detail‑oriented, organized, and committed to delivering excellent customer service.

• The…