Communication Technology Jobs in Ontario (NOW HIRING)

We Are Social is a global social media agency with offices across North America (NA), EMEA, and APAC. This is a newly created player-manager role - you'll be hands-on every day, resolving tickets, managing endpoints, and supporting ~200 users across the US and Canada, while owning strategy, stakeholder relationships, and IT direction for the region. That includes reviewing existing processes, integrating new systems into the technology stack, and driving automation to reduce manual effort.

You'll line-manage the Los Angeles IT Manager, represent North America on the global IT leadership team, and work with the business to implement the company's AI strategy.

You're a senior IT professional who hasn't lost touch with the work. You're as comfortable resolving a tricky endpoint issue or scripting an automation as you are presenting a technology roadmap - and you don't see those as contradictions. You have an instinct for spotting where a process is broken or unnecessarily manual, and you get genuine satisfaction from fixing it properly.

You're curious about where technology is heading - particularly AI - and you know how to bring a business with you on that journey. You build trust quickly, lead by example, and thrive in environments where autonomy and accountability go hand in hand.

Hands-On IT Operations

• Provide direct technical support to NA users - resolving helpdesk tickets, troubleshooting hardware and software issues, and maintaining a high standard of service across the region.
• Manage the macOS device estate for NA users - configuring and deploying endpoints via Jamf, enforcing global policies, and maintaining a secure and compliant device fleet.
• Own the onboarding and offboarding lifecycle across NA - device provisioning, account setup, access management, and hardware logistics for a distributed workforce.
• Administer and support core SaaS platforms - Google Workspace, Microsoft 365, Okta and Slack - including user provisioning, access governance, and day-to-day troubleshooting.
• Maintain endpoint security and compliance standards across the region - patch management, Jamf policy enforcement, and access reviews aligned to global IT security requirements.

Process, Automation & Integration

• Audit existing IT processes across the NA region - identifying inefficiencies and opportunities to standardise workflows such as provisioning, offboarding, device management, and ticket handling.
• Design and implement automated solutions to reduce manual effort - then document them in a shared knowledge base, leveraging the capabilities within Google Workspace, Microsoft 365, Okta, and Jamf.
• Lead the integration of new systems into the NA technology stack - evaluating fit with existing platforms, managing implementation, and ensuring new tools are securely connected, well-adopted, and aligned with global IT standards.

Strategy & Leadership

• Own and evolve the IT strategy for NA - setting priorities, identifying improvements, and ensuring the regional function scales effectively as the business grows.
• Line-manage the IT Manager in Los Angeles - setting expectations, providing guidance, and developing their capabilities as part of a high-performing small team.
• Act as the senior IT partner for NA business leaders - building trusted relationships and translating operational needs into clear technology priorities.
• Represent NA within the global IT leadership team - contributing to cross-regional strategy and ensuring NA needs are well understood and prioritised globally.
• Work with NA business leaders to implement the company's AI strategy - identifying opportunities to embed AI tools into workflows, supporting adoption, and ensuring the region gets tangible value from AI investments.
• Manage the NA IT budget and vendor relationships - balancing cost efficiency with service quality, and making the case for investment where it matters.

• 7+ years in IT roles, with experience at both a hands-on and senior level.
• Proven track record of leading IT teams and developing people.
• Experience owning IT strategy and driving meaningful change across a region or organisation.
• Strong grasp of the Apple/macOS ecosystem; Jamf administration experience.
• Demonstrable experience reviewing IT processes and implementing automation or workflow improvements.
• Experience integrating new systems or tools into an existing technology stack.
• Solid working knowledge of Google Workspace, Microsoft 365, and Okta.
• Experience working with business stakeholders on technology adoption - including emerging tools such as AI.
• Budget ownership and vendor management experience.
• Highly credible with senior business stakeholders - able to communicate technology in business terms.
• Experience managing a helpdesk queue and working to SLAs.

• Background in creative, media, or agency environments.
• Hands-on experience implementing or scaling AI tools across a business.
• Familiarity with IT governance or security frameworks (ISO 27001, SOC 2, NIST).
• Experience managing IT through periods of growth or organizational change.
• Experience with workflow automation platforms (e.g. Okta Workflows, Zapier, Make).
• Relevant certifications (ITIL, Jamf 300, or equivalent).