IT Director - Thinkingbox

AntiSocial; Toronto; On-site; CAD 125,000 - 140,000; Full time

Benefits offered by this job

On-site 5 days/week

Flexible time off

Dog-friendly offices

Unlimited coffee & snacks

Job summary

Thinkingbox in Toronto is seeking a hands-on IT Director to lead our technology environment across offices. You will own global IT operations, set the roadmap, secure and scale infrastructure, and partner with leadership to align technology with business goals.

This role blends strategy with execution—managing Apple devices, MDM, cloud infrastructure, cybersecurity, and day-to-day IT operations while mentoring teams and improving employee experience in a creative agency setting.

Qualifications

• 8–10+ years progressive IT experience with leadership
• Strong experience managing Apple environments, including Apple Business Manager and MDM platforms
• Experience supporting Windows environments and endpoint management
• Deep understanding of networking fundamentals
• Experience with cloud platforms such as AWS, GCP, Microsoft 365, identity management, SSO, and endpoint security
• Experience coordinating employee onboarding and offboarding, including device provisioning, software setup, account management
• Experience working 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 and automating workflows

Responsibilities

• Lead IT strategy, infrastructure roadmap, and technology standards across offices
• Partner with leadership to align technology investments with business objectives
• Oversee infrastructure modernization, security initiatives, cloud adoption, and operational improvements
• Develop IT policies, governance, disaster recovery, and business continuity plans
• Manage IT budgets, software licensing, hardware procurement, and vendor relationships
• Evaluate and implement new technologies to improve security, productivity, and scalability
• Act as primary escalation point for complex issues and mentor best practices
• Own the full lifecycle of Apple devices and MDM policies
• Deploy Windows workstations and provide advanced support
• Oversee networking, VPNs, identity management, and cybersecurity initiatives
• Oversee cloud infrastructure and endpoint security across AWS, GCP, and Microsoft 365
• Oversee day-to-day IT operations and provide hands-on support
• Maintain studio/office tech, AV, and production equipment
• Coordinate onboarding for new hires and manage IT assets and lifecycle

Skills

IT leadership

Apple environments

MDM platforms

Windows environments

Networking fundamentals

Cloud platforms

Identity management

Cybersecurity governance

Onboarding & offboarding

Documentation

Tools

Mosyle

Jamf

Kandji

AWS

GCP

Microsoft 365

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

$125,000 - $140,000 a year

Placement in the salary range will be based on factors such as internal equity, candidate experience, skills, and qualifications relevant to the role. If your compensation expectations fall outside of this range, we still welcome your application.

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.