Head of IT - Remote (m/w/d)

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're looking for an experienced, hands-on IT Director to lead Thinkingbox's technology environment across multiple offices. Based in our Toronto studio, you'll own our global IT operations, partnering closely with teams across North America and internationally to ensure our technology infrastructure is secure, scalable, and built to support a growing creative agency.
You'll define our IT roadmap, drive infrastructure and security initiatives, oversee day-to-day technology operations, and serve as the primary technology partner to leadership while remaining comfortable rolling up your sleeves when needed.
You'll own our Apple ecosystem, IT infrastructure, security, and technology operations while continuously improving systems, processes, and employee experience. Beyond traditional IT leadership, you'll also oversee studio technology, physical IT assets, workstation and AV environments, and partner with the Office Manager to ensure our workspaces remain functional, organized, and ready for our teams.
IT Leadership & Strategy

Own Thinkingbox's overall IT strategy, infrastructure roadmap, and technology standards across all offices.
Develop IT policies, documentation, governance, disaster recovery, and business continuity plans.
Manage IT budgets, software licensing, hardware procurement, and vendor relationships.
Act as the primary escalation point for complex technical issues while mentoring best practices across the organization.
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 new Windows workstations and provide advanced technical support when required.
Own and continuously improve wired and wireless networking, VPNs, and remote connectivity.
Lead cybersecurity initiatives, vulnerability management, incident response, and preventative security improvements.
Oversee cloud infrastructure, identity management, and endpoint security across AWS, GCP, Microsoft 365, and other core platforms.
Technical Support & IT Operations

Oversee day-to-day IT operations while providing hands-on support for complex technical issues when needed.
Support macOS, Windows, networking, software, and studio technology.
Develop scalable IT processes, documentation, automation, and long-term solutions to recurring technical issues.
Manage IT assets and lifecycle planning across the business.
Studio & Office Technology

Maintain the organization, functionality, and visual aesthetic of the studio and office spaces, partnering with the Office Manager to ensure workstations, meeting rooms, and common areas are well-equipped and ready for day-to-day operations.
Set up and maintain workstations, meeting rooms, AV equipment, monitors, TVs, and other office technology.
Manage the inventory, organization (cable management), storage, and lifecycle of IT, studio, and production equipment.
Coordinate new hire onboarding by preparing laptops, peripherals, software access, and workstation setups to ensure employees are ready on day one.
Assemble office furniture and perform occasional hardware store or equipment pickup runs as needed.
Safely lift, move, and install technology and office equipment.
Partner with Office Operations, Production, Finance, and People teams on equipment planning, technology purchases, onboarding logistics, workspace improvements, and infrastructure projects.
Serve as a trusted technology advisor to leadership and help shape operational improvements across the business.
8-10+ years of progressive IT experience, including leadership or ownership of an IT function.

• Experience supporting Windows environments and endpoint management.
• Deep understanding of networking fundamentals, including wired, wireless, VPN, firewalls, and remote connectivity.
• Experience with cloud platforms such as AWS, GCP, Microsoft 365, identity management, SSO, and endpoint security.
• Experience managing cybersecurity initiatives, vendor relationships, software licensing, and technology procurement.
• Experience coordinating employee onboarding and offboarding, including device provisioning, software setup, account management, and ensuring a seamless first-day technology experience.
• Experience supporting technology in a creative, production, or studio environment is an asset.
• Comfortable balancing strategic leadership with hands-on technical work, including setting up workstations, AV equipment, managing physical assets, and supporting the day-to-day operations of a busy creative studio.

Experience working in studio, film, digital production, or agency environments.
Experience developing cybersecurity programs and IT governance.
Background in scripting and automation (Bash, PowerShell, Python).
Relevant certifications (Jamf, Microsoft, AWS, Google Cloud, Cisco, CISSP, etc.) are an asset.
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.