Who We Are

Hi! We’re Thinkingbox, the brief to built agency. Creating innovative digital, experiential, social, and content, we partner with leading brands across industries like sports, gaming, entertainment, and technology. We believe the hands that carefully craft the work should belong to the minds that dreamed it. So while others pass the buck, we’re already building. Because our thinkers are also the makers. 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.

The Opportunity

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.

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 strong 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

Equal Opportunity

At Thinkingbox, we’re committed to creating an inclusive environment where everyone feels valued, heard, and empowered to thrive. 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. We welcome and encourage applicants of all races, ethnicities, genders, identities, abilities, ages, sexual orientations, and backgrounds to apply. Your voice matters here.

To Apply

Thank you for your interest in joining our team. Please submit your resume along with links to your online portfolio as part of your application (if applicable). Due to the volume of applications we receive, we’re unable to respond to every submission. 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. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

Placement in the salary range will be based on factors such as internal equity, candidate experience, skills, and qualifications relevant to the role. If your compensation expectations fall outside of this range, we still welcome your application.