IT Trainee

Charles IT· Service Technical
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📍 Middletown, Connecticut, United StatesTemporary

About this role

Exceptional Service, Endless Improvement, Passionate People, and Honest and Forthright. Guided by our values, we foster a culture of growth, balance, and belonging where every team member can thrive.  

We are excited to welcome a new class of trainees to our exceptional team in November 2026! Participate in our 12-week, in-house IT Trainee Program, designed to provide hands-on experience in: 

  • Our customer service approach 
  • Active Directory user and group management 
  • Printer and peripheral installations 
  • New desktop setups 
  • Office 365 administration 
  • Basic server maintenance and administration 
  • Customer network audits 
  • First-level security incidents (phishing, SPAM, Dark Web alerts) 
  • Responding to client tickets via phone and email 
  • Other duties as assigned

Responsibilities 

  • Support administrative and general office tasks 
  • Assist with IT services and projects, including on-site deliveries and equipment drop-offs 
  • Help maintain an organized office environment and support team efficiency 
  • Learn and navigate our ticketing system, a key part of our business operations 
  • Complete self-paced technical training modules and certifications 
  • Availability to work full-time (40 hours per week) for the full 12-week program 
  • Associate, Bachelor’s, or Graduate degree in Information Technology, or equivalent hands-on experience, is a plus  
  • Technical certifications such as CompTIA Server+, Security+, Network+, or Microsoft certifications (MS-900, SC-900, AZ-900) is a plus  
  • Prior experience in a help desk or related IT environment is a plus 
  • Strong motivation to learn and advance professionally 
  • Excellent organizational, time management, analytical, and problem-solving skills 
  • Clear written and verbal communication abilities 
  • Proficiency in Microsoft Office 
  • Must be 18 years of age or older 
  • Must have unrestricted authorization to work in the U.S.
  • Essential Functions include the ability to occasionally lift and carry items weighing up to 30 pounds, as well as perform tasks involving standing, walking, bending, reaching, pushing, pulling, and moving office equipment, boxes, supplies, and other materials. Some physical activity may be involved during office moves, deliveries, workspace setup, and other projects as needed.
  • Paid internship 
  • Paid training and certifications 
  • Weekly check-ins to track progress and provide mentorship 
  • Small class size (5–6 participants) for personalized support 
  • Opportunity for a full-time role as a Desktop Support Specialist upon successful completion of the program 

 

Charles IT offers a comprehensive benefits package, including medical, dental, vision, life and disability insurance, paid holidays, PTO, 401(k), and performance-based bonuses. Team members also enjoy ongoing training, professional development, quarterly team-building events, and a collaborative workplace culture.   

Commitment to Inclusion:   

Charles IT is an equal opportunity employer committed to fostering an inclusive and respectful work environment. We welcome diverse backgrounds and perspectives and do not discriminate based on any protected characteristic.

Frequently Asked Questions

Is the salary disclosed for the IT Trainee position at Charles IT?
The salary for this IT Trainee role at Charles IT is not publicly listed. Click "Apply Now" to learn more about the compensation package on their official careers page.
Where is the IT Trainee position at Charles IT located?
This IT Trainee role at Charles IT is based in Middletown, Connecticut, United States. The position is listed as on-site or hybrid. Check the full job description or apply directly to confirm the work arrangement.
Is the IT Trainee role at Charles IT full-time or part-time?
This is listed as a Temporary position. It is posted as a IT Trainee role in the Service Technical department at Charles IT.
Which team or department does the IT Trainee at Charles IT belong to?
This IT Trainee position is part of the Service Technical department at Charles IT. See the full job description for more information about the team structure and responsibilities.
How do I apply for the IT Trainee position at Charles IT?
Click the "Apply Now" button on this page. You will be redirected to Charles IT's official application portal hosted on workable where you can submit your application directly.
When was the IT Trainee job at Charles IT posted?
This IT Trainee position at Charles IT was posted on Sep 1, 2026. Apply as soon as possible — early applications are often reviewed first.
IT Trainee
Charles IT
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