IT Director - Thinkingbox

Thinkingbox; Toronto; On-site; CAD 120,000 - 170,000; Full time

Benefits offered by this job

Flexible time off

Dog-friendly offices

Comprehensive extended health benefits

Office lunches

Job summary

Thinkingbox in Toronto is seeking an experienced IT Director to lead our global technology environment. You’ll own IT strategy, infrastructure, security, and the Apple ecosystem, guiding teams across North America and beyond while rolling up your sleeves when needed.

In this role you’ll manage workstation deployments, cloud platforms, cybersecurity initiatives, vendor relationships, and day‑to‑day IT operations, ensuring a scalable, secure studio that supports a growing creative agency.

Qualifications

• 8–10+ years of progressive IT experience with leadership responsibilities.
• Experience managing Apple environments including Apple Business Manager and MDM platforms such as Mosyle, Jamf, or Kandji.
• Experience supporting Windows environments and endpoint management.
• Strong understanding of networking (wired, wireless, VPN, remote connectivity).
• Experience with cloud platforms (AWS, GCP, Microsoft 365) and identity management.
• Experience coordinating cybersecurity initiatives, vendor relationships, and software licensing.
• Experience onboarding/offboarding including device provisioning and first-day setup.
• Experience supporting technology in a creative/studio or production environment is a plus.
• Strong troubleshooting, organizational, communication, and leadership skills.
• Proactive, solution-oriented mindset with automation and process improvement focus.

Responsibilities

• Own IT strategy, infrastructure roadmap, and technology standards across offices.
• Partner with leadership to align technology investments with business goals.
• Lead modernization of infrastructure, security initiatives, and cloud adoption.
• Develop IT policies, governance, disaster recovery, and business continuity plans.
• Manage budgets, software licensing, hardware procurement, and vendor relationships.
• Evaluate new technologies to improve security, productivity, and scalability.
• Act as primary escalation point and mentor best practices across the org.
• Own Apple devices lifecycle and MDM policies; deploy Windows workstations.
• Oversee network, identity management, and endpoint security across cloud platforms.
• Lead day-to-day IT operations with hands-on support when needed.
• Support studio technology, AV equipment, and office IT infrastructure.
• Coordinate onboarding/offboarding and equipment provisioning for new hires.
• Collaborate cross-functionally with Office Ops, Production, Finance, People.

Skills

IT leadership

Apple environment management

Windows administration

Networking fundamentals

Cloud platforms

Cybersecurity initiatives

Employee onboarding

Studio IT

Troubleshooting & documentation

Automation scripting

Tools

Mosyle

Jamf

Kandji

Job description

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 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.

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, 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.

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.
• Standardize endpoint management across the organization while improving automation and compliance.
• Deploy new Windows workstations and provide 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 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.
• 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.
• 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.
• 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 and IT governance.
• Familiarity with AV, on‑set gear, 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

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.