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.

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 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 work spaces remain functional, organized, and ready for our teams.

• 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, and vendor relationships.
• 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.

• 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.
• Standardize endpoint management across the organization while improving automation and compliance.
• Deploy new Windows workstations and provide advanced technical support when required.

• 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.

• 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.

• Maintain the organization, functionality, and visual aesthetic of the studio and office spaces, partnering with the Office Manager to ensure…