Associate Systems Engineer – Endpoint Deployment & IT Support

Flexible IT is building a career-launch pathway for early talent who want hands-on endpoint deployment and IT support with real-world tools. You will work onsite from Hauppauge, NY 11788 and support client environments with structured training, mentorship, and certification reimbursement. The role includes work with Microsoft 365, Microsoft Azure, Microsoft Intune, and Sophos cybersecurity solutions, plus exposure to networking equipment and workstation deployment.

This is a 12-month associate position focused on learning through doing, with clear progression into multiple technical career paths.

What you’ll do

• 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, including deployment and replacement of 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 (when needed)
• Document configurations and completed work, and maintain accurate inventory records
• Communicate clearly and professionally with clients and team members

What you bring

• A bachelor’s degree in information technology, computer information systems, management information systems, cybersecurity, or a related field
• Genuine curiosity about how technology works, along with persistence to stay with a problem
• Strong communication and client-service instincts, including early client interaction
• The ability to follow established processes, document work, and independently apply what you learn
• A valid driver’s license and a clean driving record
• Ability and desire to work full-time from the Hauppauge office and occasionally travel to local client sites

Technologies you’ll work with

• Microsoft 365
• Microsoft Azure
• Microsoft Intune
• Sophos
• CompTIA A+, Network+, Security+
• Microsoft Azure Fundamentals (AZ-900)

Benefits and support

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

Training, mentorship, and career growth

You’ll start with a structured 90-day training period and be assigned a mentor. You will learn imaging, deployment, diagnostics, and client environments from engineers who do this work every day. The certification plan includes CompTIA A+, Network+, Security+, and Microsoft Azure Fundamentals (AZ-900).

The associate role is designed as a 12-month career launch, not an endpoint. Associates who master the required technical and client service skills become eligible to advance to multiple technical career paths, including: Support Engineer, Project Engineer, Network Operations, Cybersecurity, Compliance, and Technology Advisor.

How the team 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, with the principle that AI does not replace technical knowledge or judgment.

Compensation: USD 50,000 - 65,000 per year.