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Junior IT Specialist - OP

Job in Chicago, Cook County, Illinois, 60601, USA
Listing for: Dev.Pro
Full Time position
Listed on 2026-11-01
Job specializations:
  • IT/Tech
    Systems Administrator, IT Support
Salary/Wage Range or Industry Benchmark: 28000 - 41000 USD Yearly USD 28000.00 41000.00 YEAR
Job Description & How to Apply Below
Position: Junior IT Specialist - OP02287-01

We are hiring in Ukraine!

, a US-based outsourced software development company, we’re looking for contractors to join our global team of IT professionals helping tech companies scale their business through software engineering expertise. Operating as a remote-first company, our experts work across 55+ countries on five continents, giving us the flexibility and skillset to deliver high-quality engineering for projects of any size or complexity.

We invite a Junior IT Specialist to join our team and provide hands‑on IT support for a US-based executive’s technical environment. In this role, you’ll troubleshoot Windows systems remotely using Power Shell and command-line tools, follow written procedures, document your work, and report results clearly. You’ll also use Claude and other tools to support your technical work and contribute to the executive’s ongoing projects.

What’s in it for you:
  • Work on real-world technical challenges across the executive’s projects, building hands‑on experience in Windows administration, Power Shell, and cloud technologies
  • Build practical AI skills by using Claude in your day‑to‑day work
Is that you?
  • 1+ year of professional, hands‑on experience in IT support, help desk, IT operations, or a similar technical role
  • Working knowledge of Windows and Power Shell, including running commands, interpreting output, and reporting results accurately
  • Ability to read and review basic Python or Power Shell scripts
  • Upper‑Intermediate English level, with the ability to provide clear updates on completed work, results, and outstanding issues
  • Ability to follow written procedures, document work accurately, and clearly report any issues or blockers
  • Knowledge of basic security practices, including least‑privilege access, safe handling of credentials, and backing up before making changes
  • Attention to detail, a focus on accuracy, and the judgment to ask for help when needed
  • Ability to learn new tools and systems quickly, including the AWS console and macOS settings
Desirable:
  • Experience with AWS, Azure, or Google Cloud consoles
  • Basic networking knowledge, including IP addresses, DNS, and VPNs
  • Basic scripting skills in Power Shell, Python, or Java Script
  • Experience with Jira or a similar ticketing tool
  • Familiarity with macOS, including System Settings, privacy permissions, and Terminal
  • Basic knowledge of Linux (Ubuntu)
  • Experience supporting executives or VIP users
  • Familiarity with backup tools such as MSP
    360 or Cloud Berry
Key responsibilities and your contribution

In this role, you’ll support the executive’s technical environment and develop your skills across a range of systems and tools.

  • Provide Windows support and routine administration using Power Shell, command‑line tools, and Remote Desktop
  • Follow documented procedures, verify results, and report progress, blockers, and outcomes clearly
  • Document each task, including actions taken, results, and supporting evidence
  • Use AI assistants to investigate issues, write and review scripts, and draft responses, verifying their output before use
  • Follow security procedures, use only the access required, protect credentials, back up before making changes, and check with Security before changing security settings
  • Track technical issues through to resolution, including during weekend shifts, working within documented procedures and escalating when guidance or approval is needed
  • Contribute to practical tools and automation for the executive’s projects, learning to use Claude and other tools as needed

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