Desktop Support Technician; Windows 11 Migration – Evening, Overnight & Weekend Shifts

Desktop Support Technician (Windows 11 Migration) – Evening, Overnight & Weekend Shifts

Location: Boston, MA (Main Campus and Satellite Locations)

Duration: Approximately 6 Months (Potential Contract-to-Hire Opportunity)

Start Date: ASAP

This position is designed specifically for candidates seeking evening, overnight, and weekend work
. Because the devices are located in high-traffic patient care areas, all upgrades must be completed outside normal business hours.

Available scheduling options include:

• Main Campus: Work begins at 8:00 PM or later
• Satellite Locations: Available work between 5:00 PM and 7:00 AM
• Full-Time Option: Up to 40 hours per week through a combination of evening and overnight shifts

This role is ideal for:

• Candidates seeking a second job
• Students with daytime availability constraints
• IT professionals looking for contract project work
• Individuals who prefer overnight or non-traditional schedules

Our healthcare client is seeking Desktop Support Technicians to support a critical Windows 11 migration initiative across its main campus and multiple satellite locations. Technicians will upgrade Windows 10 devices supporting the organization's Real-Time Locating System (RTLS), which tracks patients and staff throughout clinical facilities.

The work is straightforward, well-documented, and supported by an experienced team member who will provide training and guidance. Multiple openings are expected immediately, with potential for additional hires as the project expands.

There is also a possibility of contract-to-hire conversion for high-performing consultants.

• Upgrade Windows 10 devices to Windows 11
• Support approximately 145 RTLS workstations and kiosks throughout healthcare facilities
• Follow established migration procedures and deployment checklists
• Perform basic validation after upgrades to ensure systems are operational
  
  Maintain accurate documentation and project status updates
• Work independently after training while coordinating with project leadership
• Maintain clean and organized work areas in patient and staff environments
• Adhere to all healthcare IT and facility policies

• Primary work performed at the main Boston facility
• Evening and overnight schedule beginning at 8:00 PM
• Potential for up to 40 hours per week
• Travel to regional locations including:
• Foxborough
• Chestnut Hill
• Merrimack Valley
• Work performed during evening and overnight windows between 5:00 PM and 7:00 AM
• Reliable transportation required

• Experience working with Windows operating systems
• Strong communication and customer service skills
• Ability to follow documented procedures and work independently
• Excellent organizational skills and attention to detail
• Professional attitude and dependable work ethic

• Windows 10 to Windows 11 migration experience
• PC deployment, refresh, or hardware rollout experience
• Healthcare, hospital, or clinical IT experience
• Familiarity with Dell desktop environments

• One-on-one training provided by existing project staff
• Detailed documentation and migration checklists supplied
• No advanced testing experience required

Candidates must complete all required occupational health clearances before starting, including:

• Required vaccinations/immunizations
• TB screening
• Additional healthcare onboarding requirements as needed

• Single video interview with project leadership

Seeking reliable technicians who are comfortable working evenings, nights, and weekends and can help deliver a time-sensitive Windows 11 migration project within a healthcare environment.