IT Specialist - Thinkingbox

Thinkingbox•Toronto, ON

5d•CA$65,000 - CA$75,000•Hybrid

About The Position

We are seeking an experienced and proactive IT Specialist to lead the technology environment at Thinkingbox's Toronto office and remotely support our offices in Chicago and Salt Lake City. In this role, you will own our Apple ecosystem end-to-end—including device lifecycle management, integrations, identity systems, automations, and security posture. You'll design and maintain scalable processes, support a hybrid creative/production environment, and ensure our teams have reliable, secure, and high-performing technology. This is a hands-on role for someone who brings strong technical depth, operational maturity, and the ability to continuously improve and standardize how IT functions across the studio. We're looking for someone who takes a preventative approach to technology—not just solving problems as they arise, but identifying opportunities for improvement, reducing manual work through automation, and building systems and processes that help prevent issues before they happen. Success in this role means anticipating the needs of the business, proactively identifying risks, and continuously strengthening our technology environment to support a growing creative organization.

Requirements

Must be on-site 5 days/week at our Toronto studio.
3–5+ years in an IT Specialist, Systems Administrator, or similar role.
Strong experience with Apple Business Manager and MDM platforms (Mosyle, Jamf, Kandji).
Solid macOS administration, device compliance, identity/SSO management, and endpoint security skills.
Experience deploying and troubleshooting Windows workstations using centralized management tools.
Linux familiarity, including CLI troubleshooting, basic server provisioning, and working with Docker containers.
Ability to automate workflows using Bash or PowerShell, with Git for version control.
Strong understanding of on-premise and basic cloud networking, including troubleshooting wired, wireless, and VPN environments.
Working knowledge of AWS or GCP and the ability to assist with cloud resource management and monitoring.
Experience supporting technical setups in creative or production environments is a strong asset.
Strong communication and documentation skills.
A proactive mindset with a passion for continuous improvement—you naturally look for ways to automate repetitive tasks, eliminate friction, and strengthen systems before issues arise.
Ability to lift 50 lbs and support hands-on studio and workspace setups.

Nice To Haves

Experience working in studio, film, digital production, or agency environments.
Familiarity with AV, on-set gear, or production workflows.
Background in scripting/automation (Bash, Python) or modern identity systems.
Experience leading IT process improvements, infrastructure modernization, or automation initiatives.

Responsibilities

Oversee the full lifecycle of Apple devices—procurement, deployment, configuration, compliance, and retirement.
Architect, implement, and maintain MDM policies through Mosyle or similar enterprise Apple management platforms.
Develop and enforce configuration standards, baseline profiles, and automated deployment workflows.
Proactively monitor device health, patching, compliance, and security posture to ensure systems remain reliable, secure, and aligned with industry best practices.
Continuously identify opportunities to improve device management, automate routine tasks, and enhance the employee technology experience.
Manage and deploy Windows workstations using centralized configuration management tools.
Troubleshoot Windows OS and application issues while identifying root causes and implementing long-term solutions to reduce recurring issues.
Use Linux command-line tools to troubleshoot and maintain systems.
Provision and maintain simple cloud-based Linux servers.
Build and manage Docker containers.
Write and maintain Bash or PowerShell scripts to automate IT workflows and reduce manual overhead.
Use Git for version control and collaboration on scripts and infrastructure changes.
Continuously look for opportunities to streamline repetitive tasks through automation.
Support and troubleshoot wired, wireless, VPN, and remote connectivity issues.
Apply a strong understanding of on-premise networking and foundational cloud networking concepts to maintain reliable infrastructure.
Support AWS or GCP environments, including assisting with resource management and monitoring.
Help improve cloud operations through documentation, automation, and ongoing optimization.
Manage identity access and SSO systems using least-privilege principles.
Monitor compliance, encryption, OS versions, and overall device security posture.
Continuously assess the technology environment for opportunities to strengthen security, improve reliability, and reduce operational risk.
Improve security practices, documentation, and operational automations.
Administer cloud tools, integrations, and connectivity across devices and business applications.
Lead incident response for device issues, security alerts, and access escalations while implementing preventative measures to reduce future incidents.
Proactively monitor and maintain our technology environment to minimize downtime while providing advanced troubleshooting for macOS, networking, software, and studio-related equipment.
Implement and maintain asset management systems for internal and production gear.
Evaluate and implement new tools, hardware, automations, and processes that improve efficiency, reduce manual work, and enhance the employee experience.
Identify recurring technical issues, analyze root causes, and implement long-term solutions rather than temporary fixes.
Create clear, organized documentation for processes, onboarding, troubleshooting, and system administration to support consistency and scalability.
Support workstation and meeting room setups, power/cable needs, AV requirements, and production equipment integration.
Guide best practices for technical setups in studio environments, including connectivity and gear handling.
Maintain organized storage, equipment tracking, and infrastructure readiness for on-site teams.
Partner proactively with Office Operations, Production, and Finance to anticipate technology needs, align equipment purchases with business priorities, and support hardware refresh planning.
Contribute to planning and execution of technology improvements, infrastructure upgrades, and workspace enhancements.
Buy and sell equipment on Marketplace as needed.