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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, 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
Support the day-to-day health of IT systems
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
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
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
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
Network expansions or upgrades
Partner with the IT Director on larger initiatives requiring additional technical depth
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
System Dependencies
Ensure documentation supports scalability and knowledge transfer
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