Creating innovative digital, experiential, social, and content, we partner with leading brands across industries like sports, gaming, entertainment, and technology. So while others pass the buck, we’re already building. Culture is at the heart of who we are, and our offices are hubs of natural collaboration.

From hanging out with our office dogs to enjoying Thursday happy hours, we keep our work environment vibrant, welcoming, and fun. Each year, we also encourage our people to spend a month exploring the world, whether that means working from another office or even from the beaches of Mexico, to expand their perspectives and bring fresh inspiration back to the team. 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.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.

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.

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.



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.

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. Support AWS or GCP environments, including assisting with resource management and monitoring.

Help improve cloud operations through documentation, automation, and ongoing optimization. Continuously assess the technology environment for opportunities to strengthen security, improve reliability, and reduce operational risk.

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. 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. 3–5+ years in an IT Specialist, Systems Administrator, or similar role. ~ 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. ~ 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.

Background in scripting/automation (Bash, Python) or modern identity systems.

Experience leading IT process improvements, infrastructure modernization, or automation initiatives. 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 Seasonal celebrations and gatherings throughout the year Office lunches Access to industry events, learning opportunities, and non-profit outreaches Dog-friendly offices Unlimited coffee, drinks, and snacks Flex work and travel options Placement in the salary range will be based on factors such as internal equity, candidate experience, skills, and qualifications relevant to the role. We believe that diversity is our creative strength – it's the range of perspectives, experiences, and backgrounds that fuels our best ideas and most innovative solutions.

Please submit your resume along with links to your online portfolio as part of your application (if applicable). However, all applications are kept in our talent database and will be considered for future opportunities. We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information.

These tools assist our recruitment team but do not replace human judgment. If you would like more information about how your data is processed, please contact us.

📌 IT Specialist Temp (Toronto)
🏢 Thinkingbox
📍 Toronto