Onsite Help Desk Engineer

Onsite Help Desk Engineer (Level 2)

Location: New York, NY (On-site)

Employment Type: Full-Time

About Dega Systems

At Dega Systems, we believe technology should empower organizations, not slow them down.

For more than 25 years, we've helped small businesses and nonprofit organizations throughout the New York Metro area build secure, reliable, and scalable technology environments. From managed IT services and cybersecurity to cloud solutions and VoIP communications, we become trusted technology partners for our clients, not just another vendor.

As a growing Managed Service Provider (MSP), our engineers work with a wide variety of technologies, industries, and environments. If you enjoy solving challenging technical problems, building relationships with clients, and continuously learning, you'll thrive here.

About the Role

We're looking for an experienced Level 2 Onsite Help Desk Engineer who enjoys working directly with clients and taking ownership of technical issues from start to finish.

This is more than a desktop support position. You'll serve as a trusted technical resource for multiple organizations, resolving complex end-user issues, maintaining IT infrastructure, and proactively identifying opportunities to improve client environments.

You'll work independently at client sites while collaborating closely with our Service Desk, Projects, and Engineering teams. Success in this role requires strong troubleshooting skills, professionalism, excellent communication, and the confidence to make sound technical decisions in the field.

If you enjoy variety, autonomy, and building long-term relationships with clients, we'd love to meet you.

What You'll Do

• Provide white-glove onsite IT support for a portfolio of business clients.
• Troubleshoot and resolve advanced desktop, laptop, printer, mobile device, and peripheral issues.
• Diagnose Windows and macOS operating system issues.
• Install, configure, and maintain workstations, laptops, docking stations, and endpoint devices.
• Support Microsoft 365, Outlook, Teams, OneDrive, and SharePoint.
• Troubleshoot Active Directory, Microsoft Entra ID (Azure AD), user permissions, and Group Policy issues.
• Resolve networking issues involving TCP/IP, DNS, DHCP, VPN connectivity, wireless networking, and switching.
• Configure and support VoIP phone systems and endpoint devices.
• Perform hardware replacements, upgrades, and warranty diagnostics.
• Assist with office moves, workstation deployments, and onboarding/offboarding employees.
• Escalate complex infrastructure issues while gathering detailed diagnostics to accelerate resolution.
• Document work thoroughly within the PSA and maintain accurate client documentation.
• Follow established SOPs while identifying opportunities to improve internal processes.
• Participate in client technology reviews and proactively identify recurring issues or improvement opportunities.
• Deliver exceptional customer service while educating users in a professional and approachable manner.

What Makes You Successful

You're someone who

• Enjoys solving difficult technical problems.
• Can prioritize competing requests in a fast-paced MSP environment.
• Takes ownership instead of waiting to be told what to do.
• Communicates clearly with both technical and non-technical audiences.
• Stays calm under pressure.
• Builds trust quickly with clients.
• Is naturally curious and enjoys learning new technologies.
• Has excellent organizational and documentation habits.
• Believes every client interaction is an opportunity to create an outstanding experience.
• Thinks proactively, identifying issues before they become outages.
• Can mentor junior engineers and share knowledge with teammates.

Required Technical Skills

• 3–5 years of Help Desk or Desktop Support experience (MSP experience strongly preferred)
• Advanced Windows 10/11 troubleshooting
• Working knowledge of macOS
• Microsoft 365 administration
• Active Directory
• Microsoft Entra ID (Azure AD)
• Group Policy
• Intune endpoint management
• Basic PowerShell experience
• TCP/IP networking fundamentals
• DNS, DHCP, VPN, VLAN, and wireless troubleshooting
• Printer deployment and troubleshooting
• Hardware diagnostics and repair
• VoIP phone support
• Experience with remote support tools
• Experience working within ticketing/PSA systems

Bonus Skills

Experience with any of the following is a plus

• NinjaOne
• Addigy
• Autotask PSA
• IT Glue
• Microsoft Defender
• Microsoft Purview
• SharePoint administration
• Hyper-V or VMware
• Backup solutions such as Veeam
• Network switches and firewalls (Cisco, SonicWall, Fortinet, Ubiquiti, Meraki)
• Apple Business Manager
• Azure Virtual Desktop
• Basic scripting and automation

Preferred Certifications

• CompTIA A+
• CompTIA Network+
• Microsoft certifications
• ITIL Foundation
• Apple Certified Support Professional (ACSP)
• Equivalent real-world experience is valued just as highly.

Why Join Dega Systems?

• Exposure to a wide variety of technologies and industries.
• Opportunity to grow into Systems Engineering, Projects, Security, or Leadership roles.
• Collaborative and supportive engineering team.
• Continuous learning and professional development.
• Meaningful work supporting organizations that rely on technology every day.
• Opportunity to make a real impact on client success.
• If you're passionate about technology, enjoy working directly with people, and want to build a career in a fast-growing MSP, we'd love to hear from you.