IT Deployment Technician – Windows 11 Upgrade Initiative

Job Title

IT Deployment Technician – Windows 11 Upgrade Initiative

Greenwich, CT (On-site)

Contract (Project scheduled to run through September)

Hourly pay of $20–$22, based on experience, with an additional $2/hour travel reimbursement. The pay range for this position is $17.00 - $24.00/hr.

We are supporting a large Windows 11 deployment project and seeking junior-level IT Deployment Technicians to assist with imaging, device rollout, troubleshooting, and end‑user support. This is an on‑site role that requires strong customer service skills and the ability to support users in a fast-paced environment. The project is scheduled to run through September, with potential for extension based on needs.

• Image, configure, and prepare Windows 11 devices according to established procedures.
• Stage, organize, and deploy equipment across designated locations.
• Assist end users during device cutovers and provide on‑site support.
• Troubleshoot issues involving user profiles, permissions, applications, and hardware peripherals.
• Validate network connectivity, mapped drives, and overall workstation functionality.
• Document deployment actions in the ticketing system; escalate issues as required.
• Collect, wipe, and process legacy devices in accordance with asset management standards.
• Coordinate daily tasks with project leads to maintain deployment timelines.

• Ability to troubleshoot in a Windows environment, including Active Directory account and permission management; experience supporting Windows 7/10/11.
• Ability to troubleshoot basic network connectivity and IP issues, map network drives, and configure PC peripherals (printers, monitors, docking stations, etc.).
• Strong customer service background with experience providing white‑glove support in person, via email, and occasionally by phone.

• Experience with Windows imaging, device deployment, or junior desktop support.
• Understanding of Windows OS fundamentals and basic networking concepts.
• Familiarity with ticketing systems and standard IT support processes.
• Ability to lift/move equipment and travel between nearby facilities if needed.
• Professional communication skills and ability to work with non‑technical users.

• Monday–Friday, standard business hours, with occasional flexibility during peak deployment periods.
• Project expected to conclude in September.

This is a Contract position based out of Greenwich, CT.

• Medical, dental & vision
• Critical Illness, Accident, and Hospital
• 401(k) Retirement Plan – Pre‑tax and Roth post‑tax contributions available
• Life Insurance (Voluntary Life & AD&D for the employee and dependents)
• Short and long‑term disability
• Health Spending Account (HSA)
• Transportation benefits
• Employee Assistance Program
• Time Off/Leave (PTO, Vacation or Sick Leave)

This position is anticipated to close on Feb 23, 2026.

The company is an equal opportunity employer and will consider all applications without regard to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.