IT Director - Thinkingbox

Who We Are
Hi! We're Thinkingbox, the brief to build 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 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.

This is a leadership role for someone who enjoys balancing strategy with execution. 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 endpoint ecosystem across both Apple and Windows environments, alongside our IT infrastructure, security, and technology operations, 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.

What You'll Be Doing

IT Leadership & Strategy

• Own Thinkingbox's overall IT strategy, infrastructure roadmap, and technology standards across all offices.
• Partner with executive leadership to align technology investments with business objectives.
• Lead infrastructure modernization, security initiatives, cloud adoption, and operational improvements.
• Develop IT policies, documentation, governance, disaster recovery, and business continuity plans.
• Manage IT budgets, software licensing, hardware procurement, warranty programs, vendor relationships, and long-term hardware lifecycle planning across the business.
• Evaluate and implement new technologies that improve security, productivity, and scalability.
• Act as the primary escalation point for complex technical issues while mentoring best practices across the organization.

Endpoint & Systems Management

• Own the full lifecycle of endpoint hardware across Apple and Windows environments, including procurement, deployment, configuration, maintenance, security compliance, warranty management, depreciation, lifecycle planning, and retirement.
• Manage MDM using Mosyle or a similar platform, developing device policies, automated workflows, and security standards.
• Standardize endpoint management across the organization while improving automation and compliance.
• Develop and execute the organization's endpoint hardware strategy across Apple and Windows devices, including workstation standards, procurement planning, hardware refresh cycles, asset management, and advanced technical support when required.

Infrastructure, Cloud & Security

• Own and continuously improve wired and wireless networking, VPNs, and remote connectivity.
• Manage identity, SSO, device security, encryption, and access controls.
• 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 Apple and Windows hardware, ensuring effective procurement, inventory management, maintenance, security compliance, depreciation, and replacement strategies.

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.
• Build and support studio hardware, including motion capture towers and production equipment.
• 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.

Cross-Functional Collaboration

• 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.

What You'll Bring

• 8–10+ years of progressive IT experience, including leadership or ownership of an IT function.
• Strong experience managing Apple environments, including Apple Business Manager and MDM platforms such as Mosyle, Jamf, or Kandji, alongside experience overseeing Windows workstation environments and enterprise hardware lifecycle management.
• Experience managing Windows environments, workstation hardware strategy, endpoint management, procurement, and lifecycle planning at scale.
• 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.
• Strong troubleshooting, organizational, communication, leadership, and documentation skills.
• A proactive, solutions-oriented mindset with a passion for improving systems, automating workflows, and preventing issues before they arise.
• 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.

Bonus Points

• Experience working in studio, film, digital production, or agency environments.
• Experience developing cybersecurity programs, IT governance, and security frameworks.
• Experience managing mixed Apple and Windows environments, including enterprise endpoint management and hardware lifecycle planning.
• Familiarity with AV, on-set gear, render infrastructure, or production workflows.
• Background in scripting and automation (Bash, PowerShell, Python).
• Relevant certifications (Jamf, Microsoft, AWS, Google Cloud, Cisco, CISSP, etc.) are an asset.

Additional Info

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