Support 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.

About the role

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.

What you'll do

Technical Troubleshooting & Resolution:

• 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 OneDrive.
• Perform basic account administration in Active Directory, Azure AD, and Microsoft 365.
• Document all work performed in the ticketing system accurately and thoroughly.

Problem Escalation Support:

• 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.

Project Execution:

• Assist with basic project tasks under the direction of 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.

Documentation & Continuous Improvement:

• Maintain accurate and up-to-date documentation in ConnectWise, 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.

Client Engagement:

• 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.

Qualifications

Education & Technical Experience:

• 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 in troubleshooting Windows Desktop OS, Microsoft 365, networking issues (DNS, DHCP, and, VPN).
• Experience with ConnectWise Manage, Automate, ScreenConnect, or similar tools preferred.

Soft Skills:

• 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.

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