IT Technician (Level 1-2)

KaleidoscopeChicago, IL
$60,000 - $70,000

About The Position

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.

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.
  • Strong hands-on experience with Microsoft 365 Administration.
  • Strong hands-on experience with Networked Hardware and Peripherals.
  • Strong hands-on experience with 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.

Responsibilities

  • 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. You will also learn to handle more cases independently over time that are above Level 1.
  • Troubleshoot and Support FileMaker client/server environments, scripts, layouts, and integrations.
  • Troubleshoot and Support Adobe Creative Cloud performance and configuration.
  • Troubleshoot and Support Microsoft 365 applications, sync issues, authentication, and desktop clients.
  • Troubleshoot and Support Copilot AI usage, adoption, and workflow integration.
  • Troubleshoot and Support MacOS and Windows environments, including Windows CAD systems.
  • Escalate true infrastructure – or architecture-level issues to the IT Director as needed.
  • Support the day-to-day health of IT systems, with opportunities to take on more ownership as experience grows, including Ubiquiti network hardware, Synology appliances, RAID health, and backup integrity, Windows Server patching, roles, and system integrations, and networked printers, IP addressing, and access controls.
  • 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 and CAD Systems, and 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, with training provided when needed.
  • Own and optimize the IT support portal using Asana and Microsoft Teams.
  • Build and Maintain Ticket Templates, SLA’s, Triage Logic, and Automated workflows and reporting.
  • Conduct monthly ticket analysis to identify trends and recommend operational improvements.
  • Improve response times, resolution quality, and user satisfaction through data-driven insights.
  • Lead small to medium-sized technical projects end-to-end, including AI Workflow Automations, FileMaker enhancements and integrations, software deployment and rollout automation, security improvements, and network expansions or upgrades.
  • Partner with the IT Director on larger initiatives requiring additional technical depth, using projects as learning opportunities to deepen technical expertise.
  • 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.
  • Ensure documentation supports scalability and knowledge transfer.
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