IT Director - Thinkingbox

About the role

Thinkingbox is seeking a hands-on IT Director to manage our global technology operations from our Toronto studio. This role balances high-level strategy with daily execution, ensuring our infrastructure remains secure and scalable while supporting our creative teams across North America and beyond.

Key facts

What you'll do

• Define and execute the global IT roadmap, infrastructure standards, and security policies.
• Manage the full hardware lifecycle for Apple and Windows environments, including procurement, deployment, and retirement.
• Oversee cloud platforms, identity management, SSO, and network connectivity.
• Lead cybersecurity initiatives, incident response, and vulnerability management.
• Act as the primary technical escalation point while mentoring staff.
• Partner with executive leadership on budget management, vendor relations, and software licensing.
• Maintain studio and office technology, including AV equipment, workstations, and production hardware.
• Coordinate new hire onboarding and offboarding logistics.
• Collaborate with the Office Manager to ensure workspace functionality and organization.

Requirements

• 8 to 10+ years of progressive IT experience with a focus on leadership or function ownership.
• Proficiency in managing Apple environments via Apple Business Manager and MDM tools like Mosyle, Jamf, or Kandji.
• Experience overseeing Windows workstation environments, including endpoint management and hardware strategy.
• Deep knowledge of networking, including firewalls, VPNs, and wireless infrastructure.
• Experience with cloud environments such as AWS, GCP, and Microsoft 365.
• Proven ability to manage cybersecurity programs, vendor contracts, and technology procurement.
• Ability to work on-site 5 days per week in the Toronto office.
• Physical capability to lift, move, and install office and production equipment.

Nice to have

• Background in creative, digital production, or agency settings.
• Experience with IT governance and security frameworks.
• Familiarity with production-specific gear, render infrastructure, or AV setups.
• Scripting and automation skills using Python, Bash, or PowerShell.
• Relevant industry certifications such as CISSP, AWS, Google Cloud, Cisco, or Jamf.

Skills & tools

• Apple Business Manager, Mosyle, Jamf, Kandji
• Windows Enterprise Management
• AWS, GCP, Microsoft 365
• Networking (Wired, Wireless, VPN, Firewalls)
• Identity Management and SSO
• AV and Studio Hardware

Practical notes

• This role is based on-site 5 days per week in Toronto.
• Benefits include comprehensive extended health coverage, flexible time off, and office perks like catered lunches and dog-friendly spaces.
• Please submit a resume and a link to an online portfolio if applicable.