What You’ll Be Doing Apple Infrastructure Ownership - 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.

Windows

Support - 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.

Linux

Familiarity - Use Linux command-line tools to troubleshoot and maintain systems.

- Provision and maintain simple cloud-based Linux servers.
- Build and manage Docker containers. Scripting & Automation - 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. Networking - Support and troubleshoot wired, wireless, VPN, and remote connectivity issues.
- Apply a solid understanding of on‑premise networking and foundational cloud networking concepts to maintain reliable infrastructure. Cloud - Support AWS or GCP environments, including assisting with resource management and monitoring.
- Help improve cloud operations through documentation, automation, and ongoing optimization. Security, Identity & Systems Management - 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.

Technical

Support & Operational Leadership - 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. Studio & Workspace Technology - 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. Cross‑Functional Collaboration - 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.



What You’ll Bring - 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.

Bonus

Points - 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.

Additional

Info - Must be on‑site 5 days/week at our Toronto office - Flexible time off, including paid vacation and sick days - Consistent culture and team‑building events - Employee recognition and incentive programs - Seasonal celebrations and gatherings throughout the year - Office lunches - Branded company swag - Access to industry events, learning opportunities, and non‑profit outreaches - Dog‑friendly offices - Unlimited coffee, drinks, and snacks - Flex work and travel options - Comprehensive extended health benefits

📌 IT Specialist - Thinkingbox (Vancouver)
🏢 twentysix
📍 Vancouver