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're looking for a proactive, hands-on IT Specialist to lead the technology environment for Thinkingbox's Toronto office while supporting our Chicago and Salt Lake City studios remotely.
You'll own our Apple ecosystem, IT infrastructure, security, and day-to-day technology operations while building scalable processes that keep our teams productive and our systems secure.
This role goes beyond traditional IT support. You'll also help manage studio technology, physical IT assets, workstation and AV setups, and partner with the Office Manager to keep our workspace organized, functional, and ready for our teams.
What You’ll Be Doing
- Endpoint & Systems Management
- Own the full lifecycle of Apple devices, including procurement, deployment, configuration, compliance, and retirement.
- Manage MDM using Mosyle or a similar platform, developing device policies, automated workflows, and security standards.
- Deploy, manage, and troubleshoot Windows workstations and provide basic Linux administration, including Docker and cloud-hosted servers.
- Write and maintain Bash or PowerShell scripts to automate workflows, using Git for version control. Infrastructure, Cloud & Security
- Support wired and wireless networking, VPNs, and remote connectivity.
- Assist with AWS or GCP environments, monitoring resources and improving cloud operations.
- Manage identity, SSO, device security, encryption, and access controls while responding to security incidents and implementing preventative improvements. Technical Support & IT Operations
- Provide advanced support for macOS, Windows, networking, software, and studio technology.
- Manage IT assets and documentation, improve processes through automation, and implement long-term solutions to recurring technical issues.
- Evaluate and deploy new hardware, software, and tools that improve the employee experience and operational efficiency. Studio & Office Technology
- Set up and maintain workstations, meeting rooms, AV equipment, monitors, TVs, and other office technology.
- Build and support studio hardware, including motion capture towers and production equipment.
- Manage the inventory, organization, storage, and lifecycle of IT, studio, and production equipment.
- Assemble office furniture, perform occasional hardware store or equipment pickup runs, and partner with the Office Manager to keep the studio organized, functional, and ready for day-to-day operations.
- Safely lift, move, and install technology and office equipment as needed. Cross-Functional Collaboration
- Partner with Office Operations, Production, and Finance on equipment planning, technology purchases, workspace improvements, and infrastructure projects.
What You’ll Bring
- 3–5+ years of experience in an IT Specialist, Systems Administrator, or similar role.
- Strong experience managing Apple environments, including Apple Business Manager and MDM platforms such as Mosyle, Jamf, or Kandji.
- Experience supporting Windows devices, basic Linux administration, and Docker containers.
- Proficiency with Bash or PowerShell scripting and Git for automation and version control.
- Solid understanding of networking fundamentals, including wired, wireless, VPN, and remote connectivity.
- Working knowledge of AWS or GCP, identity management, SSO, and endpoint security.
- Experience supporting technology in a creative, production, or studio environment is an asset.
- Strong troubleshooting, organizational, communication, and documentation skills.
- A proactive, solutions-oriented mindset with a passion for improving systems, automating workflows, and preventing issues before they arise.
- Comfortable performing hands-on work, including lifting up to 50 lbs, setting up workstations and AV equipment, assembling furniture, managing physical assets, and supporting the day-to-day operation of a busy creative studio.
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.
Skills Required
- On-site 5 days/week at 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)
- 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 Docker containers
- Ability to write and maintain Bash or PowerShell scripts and use Git for version control
- Strong understanding of on-premise and basic cloud networking, wired/wireless/VPN troubleshooting
- Working knowledge of AWS or GCP to assist with cloud resource management and monitoring
- Experience supporting technical setups in creative or production environments
- Strong communication and documentation skills
- Proactive mindset focused on continuous improvement and automation
- Ability to lift 50 lbs and support hands-on studio and workspace setups
- Familiarity with AV, on-set gear, production workflows
- Background in scripting/automation (Bash, Python) or modern identity systems
- Experience leading IT process improvements, infrastructure modernization, or automation initiatives
What We Do
Thinkingbox is a brand experience agency shaping the future of brands through craft and curiosity
