Associate Systems Engineer – Endpoint Deployment & IT Support

Flexible IT is building a practical, career-launch environment for people who want to get hands-on with the systems that power real businesses. This 12-month onsite role in Hauppauge, NY 11788 combines structured training, mentorship, and professional development alongside work deploying endpoints, supporting users, and helping maintain secure client environments. You will also have support for certifications, including CompTIA A+, Network+, Security+, and Microsoft Azure Fundamentals (AZ-900), plus a company vehicle for local client travel.

What you’ll do

You’ll support client technology by enrolling and configuring devices, deploying endpoints, and troubleshooting issues across common Microsoft and security tools. The work includes hands-on tasks like imaging and configuration, verification of deployments, and clear documentation so clients and teammates stay aligned.

• Enroll and configure devices using Microsoft Intune
• Support Microsoft 365 and Microsoft Azure environments
• Install and verify Sophos cybersecurity protection
• Troubleshoot hardware, software, and connectivity problems
• Perform hardware diagnostics and basic repairs
• Image and configure desktops and laptops
• Prepare systems for new employees
• Deploy and replace workstations, monitors, printers, and related equipment
• Collaborate with engineers on larger deployments and technology projects
• Visit local client sites to install, support, and verify equipment
• Document configurations, completed work, and maintain accurate inventory records
• Communicate clearly and professionally with clients and team members

Tools and platforms you’ll work with

You’ll build competency across the technologies clients rely on, including Microsoft 365, Microsoft Azure, Microsoft Intune, and Sophos. Training also includes relevant foundations in Microsoft Azure Fundamentals (AZ-900).

What you bring

• A bachelor’s degree in information technology (or related field)
• Genuine curiosity about how technology works and persistence to stay with a problem
• Strong communication and client-service instincts, especially when interacting with clients early
• The ability to follow established processes, document your work, and apply what you learn independently
• A valid driver’s license and a clean driving record
• Ability and desire to work full-time from the Hauppauge office, with occasional travel to local client sites

Benefits and development

• Health insurance
• Paid time off
• Retirement savings plan
• Certification reimbursement and dedicated professional development opportunities
• Company vehicle

You’ll get structured training and mentorship from engineers who do this work every day. The program includes a mentor, a structured 90-day training period, and certification support. Relevant certifications include CompTIA A+, Network+, Security+, and Microsoft Azure Fundamentals (AZ-900).

Where this role leads

This is a 12-month career launch position designed as a starting point. Associates who master the technical and client service skills required in this role become eligible to advance to one of several technical career paths, including:

• Support Engineer
• Project Engineer
• Network Operations
• Cybersecurity
• Compliance
• Technology Advisor

How Flexible IT works

Flexible IT combines decades of practical IT experience with modern AI tools. The team uses AI to accelerate troubleshooting, build internal tools, automate routine work, monitor workflows, and learn more quickly, while emphasizing that AI does not replace technical knowledge or judgment.

Salary: USD 50,000 to 65,000 per year.