Associate Systems Engineer - Endpoint Deployment & IT Support

A Better Starting Point for Your IT Career
In many entry-level IT jobs, you learn one environment: one network, one set of applications, and one way of doing things. It can take years to gain broader exposure.
At Flexible IT, the learning curve is different. You will gain hands-on experience across a wide range of client environments, giving you early exposure to the technology that real businesses rely on every day.
In your first year, you will work across more technical environments than many IT professionals encounter during their first five years at a single organization. That breadth helps you build a stronger technical foundation, discover where you want to specialize, and launch your IT career with practical experience from the start.

What You Get
Hands-on work with the technology that businesses actually use. You will work with Microsoft 365, Microsoft Azure, Microsoft Intune, Sophos cybersecurity solutions, networking equipment, workstations, and servers.
Exposure across industries. You will see how professional firms, healthcare organizations, manufacturers, distributors, municipalities, and other organizations use technology.
Structured training and mentorship. You will not be handed a ticket queue and wished luck. You will learn imaging, deployment, diagnostics, and client environments from engineers who do this work every day. You will be assigned a mentor and begin with a structured 90-day training period.
Certifications we pay for. We provide certification reimbursement and dedicated professional development opportunities. Relevant certifications include CompTIA A+, Network+, Security+, and Microsoft Azure Fundamentals (AZ-900).
Benefits. Health insurance, paid time off, and a retirement savings plan.
A company vehicle. A company vehicle is provided for travel between our Hauppauge office and local client sites during the workday.

Where This Leads
Associate Systems Engineer is a starting point, not a destination. This role is designed as a 12-month career launch position. Associates who master the required technical and client service skills become eligible to advance to one of several technical career paths.

Career paths include:

• Support Engineer: Deeper troubleshooting and broader client responsibility
• Project Engineer: Larger deployments, project work, and client technical leadership
• Network Operations: Monitoring, infrastructure, and systems
• Cybersecurity: Endpoint security, threat monitoring, security tools, vulnerability remediation, and client security initiatives
• Compliance: Helping clients meet regulatory compliance and technology requirements through assessments, documentation, control implementation, and remediation
• Technology Advisor: Strategic client guidance, technology planning, and long-term relationship ownership

How We Work
We combine decades of practical IT experience with modern AI tools. Our team uses AI to accelerate troubleshooting, build internal tools, automate routine work, monitor workflows, and learn more quickly. We believe that AI does not replace technical knowledge or judgment. It strengthens the capabilities of people who understand the systems, the clients, and the work.

What You Will Do

• Enroll and configure devices through 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
• Work with engineers on larger deployments and technology projects
• Visit local client sites to install, support, and verify equipment
• Document configurations and completed work
• Maintain accurate inventory records
• Communicate clearly and professionally with clients and team members

What We Are Looking For

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

About Flexible IT
Flexible IT has been helping Long Island businesses use technology for 43 years. We are SOC 2 Type II compliant and have built a team around people who enjoy solving problems and explaining them clearly. We are large enough to give you serious technical work and small enough that your efforts will make a real impact.

If you want to begin your IT career by doing real technical work, learning from experienced engineers, and seeing how technology operates across many different businesses, we would like to meet you.
Apply today.