IT Technician; Level 1-2

Role Summary

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 File Maker 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.

• Advanced Technical Support & Escalations:
  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, and gradually take on higher‑level cases.
• Troubleshoot and Support:
  • File Maker client/server environments, scripts, layouts, and integrations
  • Adobe Creative Cloud performance and configuration
  • Microsoft 365 applications, sync issues, authentication, and desktop clients
  • Copilot AI usage, adoption, and workflow integration
  • macOS and Windows environments, including Windows CAD systems
  • Escalate true infrastructure – or architecture‑level issues to the IT Director as needed.
• Systems, Infrastructure & Security Operations:
  Support the day‑to‑day health of IT systems, with opportunities to take on more ownership as experience grows:
  • Ubiquiti network hardware
  • Synology appliances, RAID health, and backup integrity
  • Windows Server patching, roles, and system integrations
  • Networked printers, IP addressing, and access controls
  • Assist with security hardening initiatives and system updates
  • Proactively identify risks, performance issues, and improvement opportunities
• Hardware & Asset Lifecycle Management:
  Manage the full hardware lifecycle for Apple Devices, Windows Workstations and 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, with training provided when needed.
• Support Operations & Ticketing Ownership:
  Own and optimize the IT support portal using Asana and Microsoft Teams; build and maintain ticket templates, SLAs, triage logic, 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.
• Project Ownership & Innovation:
  Lead small to medium‑size technical projects end‑to‑end, including AI workflow automations, File Maker enhancements and integrations, software deployment and rollout automation, security improvements, 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.
• Documentation & Knowledge Management:
  Create and maintain clear, up‑to‑date technical documentation; develop setup guides, troubleshooting workflows, and configuration documentation; maintain records for hardware, software, integrations, system dependencies; ensure documentation supports scalability and knowledge transfer.

• 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…