IT Technician (Level 1-2)

IT Technician (Level 1-2) Kaleidoscope is a creative collective of thinkers, designers and makers that together connect people and brands. Apply Here! 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 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. Key Responsibilities: 1. 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. You will also learn to handle more cases independently over time that are above Level 1. • Troubleshoot and Support: o FileMaker client/server environments, scripts, layouts, and integrations o Adobe Creative Cloud performance and configuration o Microsoft 365 applications, sync issues, authentication, and desktop clients o Copilot AI usage, adoption, and workflow integration o MacOS and Windows environments, including Windows CAD systems • Escalate true infrastructure – or architecture-level issues to the IT Director as needed. 2. Systems, Infrastructure & Security Operations: • Support the day-to-day health of IT systems, with opportunities to take on more ownership as experience grows: o Ubiquiti network hardware o Synology appliances, RAID health, and backup integrity o Windows Server patching, roles, and system integrations o Networked printers, IP addressing, and access controls • Assist with security hardening initiatives and system updates • Proactively identify risks, performance issues, and improvement opportunities 3. Hardware & Asset Lifecycle Management: • Manage the full hardware lifecycle for: o Apple Devices o Windows Workstations and CAD Systems o 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 4. Support Operations & Ticketing Ownership: • Own and optimize the IT support portal using Asana and Microsoft Teams. • Build and Maintain: o Ticket Templates o SLA’s o Triage Logic o 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. 5. Project Ownership & Innovation: • Lead small to medium-sized technical projects end-to-end, including: o AI Workflow Automations o FileMaker enhancements and integrations o Software deployment and rollout automation o Security Improvements o 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 6. Documentation & Knowledge Management: • Create and maintain clear, up-to-date technical documentation • Develop setup guides, troubleshooting workflows, and configuration documentation • Maintain records for: o Hardware o Software o Integrations o System Dependencies • Ensure documentation supports scalability and knowledge transfer Qualifications: • 3-5+ Years of progressive experience in IT support, systems administration, or a related role. • Strong hands-on experience with: o MacOS and Windows Systems o Microsoft 365 Administration o Networked Hardware and Peripherals o 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 Key Competencies: •Advanced Technical Troubleshooting & Problem-Solving •Systems & Infrastructure Management •Process Automation & AI Enablement •Project Ownership & Execution •Documentation & Knowledge Sharing •Collaboration & Escalation Judgement •Willingness to Learn & Grow Mindset KPIs for Success: •Support Effectiveness: Ticket resolution time, reduction in escalations to IT Director •System Stability: Uptime and performance of FileMaker, networks, and core systems •Operational Efficiency: Automation adoption and workflow improvements •User Experience: Employee satisfaction with IT support and tools •Documentation Quality: Completeness, clarity, and accuracy of technical documentation Salary Range: $60,000 - $70,000 USD Employment Terms: Kaleidoscope is an Equal Opportunity Employer and does not discriminate against any employee or applicant on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other protected status under applicable law. All new hires participate in a 90-day introductory period designed to ensure mutual fit, provide onboarding support, and align with company objectives. Department Information Technology Locations Chicago Remote status Hybrid