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Kaleidoscope® Logo Kaleidoscope® · IT - Administration

IT Technician (Level 1-2)

United States, Chicago Employment contract 60000.00 - 70000.00 USD / Year · Job Posted May 29, 2026
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Job Description

Kaleidoscope is seeking a motivated and technically curious Level 1–2 IT Technician to serve as the technical support backbone of our IT team. This role will own the resolution of most day-to-day technical issues across software, hardware, systems, and integrations, while also serving as a learning and growth opportunity within a modern, creative, and evolving IT environment. The Level 1–2 IT Technician supports both creative and operational teams, ensuring reliable performance of FileMaker systems, creative workflows, AI tools, and core infrastructure. This position is not expected to know every system or tool on day one. Success in this role comes from strong fundamentals, problem-solving ability, and a willingness to learn—supported by hands-on experience, documentation, and direct partnership with the IT Director. This role is designed to improve operational efficiency, expand automation and AI adoption, and enable the IT Director to focus on high-level strategy, architecture, and innovation, while the technician continues to build deeper technical expertise over time.

Job Responsibility

  • Serve as the primary resolver for Level 1-2 technical issues across the organization
  • Handle cases from Level 1 support, resolving the majority of software, integration, and hardware issues independently
  • Troubleshoot and Support FileMaker client/server environments, Adobe Creative Cloud, Microsoft 365, Copilot AI, MacOS and Windows environments
  • Escalate true infrastructure-level issues to the IT Director as needed
  • Support the day-to-day health of IT systems such as Ubiquiti network hardware, Synology appliances, Windows Server, networked printers, IP addressing
  • Assist with security hardening initiatives and system updates
  • Proactively identify risks, performance issues, and improvement opportunities
  • Manage the full hardware lifecycle for Apple Devices, Windows Workstations, CAD Systems, Servers, printers, and peripherals
  • Maintain accurate asset tracking, warranty management, and device retirement plans
  • Image, configure, and deploy new workstations for employees
  • Support and maintain large-format printers and Xerox machines
  • Own and optimize the IT support portal using Asana and Microsoft Teams
  • Build and Maintain Ticket Templates, SLA's, Triage Logic, Automated workflows and reporting
  • Conduct monthly ticket analysis to identify trends and recommend operational improvements
  • Lead small to medium-sized technical projects end-to-end including AI Workflow Automations, FileMaker enhancements and integrations, Software deployment, Security Improvements, Network expansions or upgrades
  • Partner with the IT Director on larger initiatives
  • Contribute to continuous improvement of IT processes, automation, and scalability
  • Create and maintain clear, up-to-date technical documentation
  • Develop setup guides, troubleshooting workflows, and configuration documentation
  • Maintain records for hardware, software, integrations, and system dependencies

Requirements

  • 3-5+ Years of progressive experience in IT support, systems administration, or a related role
  • Strong hands-on experience with: MacOS and Windows Systems
  • Microsoft 365 Administration
  • Networked Hardware and Peripherals
  • FileMaker Environments
  • Experience supporting creative teams and complex software workflows
  • Familiarity with AI tools, automation platforms, and modern IT tooling
  • Ability to independently troubleshoot complex technical issues
  • Strong organizational, documentation, and time-management skills
  • Excellent communication skills with both technical and non-technical users
  • A curiosity-driven mindset with a desire to continuously learn and grow
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