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About the Role

We are seeking an experienced, hands-on IT Director to lead our technology environment across multiple offices. Based in our Toronto studio, you will own our global IT operations, partnering with teams across North America and internationally to ensure our technology infrastructure is secure, scalable, and supports a growing creative agency. This leadership role requires balancing strategy with execution, defining the IT roadmap, driving infrastructure and security initiatives, overseeing daily technology operations, and serving as the primary technology partner to leadership while remaining hands-on when needed. You will own our Apple ecosystem, IT infrastructure, security, and technology operations, continuously improving systems, processes, and employee experience. Additionally, you will oversee studio technology, physical IT assets, workstation and AV environments, and partner with the Office Manager to ensure our workspaces are functional and organized.

Responsibilities

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 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.
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.

Requirements

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.
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.
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.

Skills

Apple ecosystem management
IT infrastructure
Security
Technology operations
Apple Business Manager
MDM platforms (Mosyle, Jamf, Kandji)
Windows endpoint management
Networking fundamentals
Cloud platforms (AWS, GCP, Microsoft 365)
Identity management
SSO
Endpoint security
Cybersecurity initiatives
Vendor relationship management
Software licensing
Technology procurement
Employee onboarding and offboarding
Troubleshooting
Organizational skills
Communication skills
Leadership skills
Documentation skills
Scripting and automation (Bash, PowerShell, Python)
AV equipment setup and maintenance
Studio hardware support
Motion capture towers
Production equipment support
IT asset management
Disaster recovery planning
Business continuity planning

Location

Toronto

Work Type

On-site

Experience Level

8-10+ years of progressive IT experience
Leadership or ownership of an IT function

Salary/Compensations

$125,000 - $140,000 a year

Benefits

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

About the Company

Thinkingbox is a brief to build agency creating innovative digital, experiential, social, and content.
We partner with leading brands across industries like sports, gaming, entertainment, and technology.
Culture is at the heart of who we are, and our offices are hubs of natural collaboration.
We keep our work environment vibrant, welcoming, and fun.
Each year, we encourage our people to spend a month exploring the world to expand their perspectives and bring fresh inspiration back to the team.

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.