IT Support Specialist - 12 Month Contract

At Rethink, our promise to you is that you will do the best work of your career. We know that to do the best work, we have to create and promote an environment where people are happy, inspired, appreciated, empowered, and having fun. Our ability to back that promise is rooted in our commitment to remain as a creative independent agency. So if you are ready to do the best work of your career while having fun, then read on. 

We are looking for an IT Support Specialist to help us support our macOS client platform and IT Infrastructure services in order to deliver a seamless and consistent employee experience. As a key member of the IT team, you will be working with a talented team of IT technicians that are responsible for supporting critical IT services. 

This role will be based in Toronto, primarily supporting Rethink’s Toronto, New York and Montreal Offices but will support all office locations. 

The Opportunity

• Provide Tier 1 technical hardware and software support to staff via our ticketing system, real-time messaging, in-office assistance, and remote support.


• Support the macOS client deployment workflows built with Apple Business Manager, Simple MDM and Munki for new and re-deployed devices.


• Provision and support iOS devices for end users.


• Support additional Tier 1 IT Infrastructure services as required (G Suite, SAML, Zendesk, Slack, Jump Cloud, O365 etc).


• Provide resolution of issues for on-site equipment, such as boardroom AV equipment and printers.


• Maintain tracking of assets in our asset tracking system.


• Provide new staff IT account creation, logistics, and onboarding training.


• Maintain support documentation, writing internal knowledge base articles as required.


• Assist with new project rollouts.

What you’ll bring:

• Post-secondary education or relevant work experience


• Cloud-based experience with SaaS applications functions (G-Suite, Jump Cloud, Zendesk, Slack)


• Intermediate knowledge of macOS and with Apple technology


• Some knowledge of Python and Shell scripting not required, but nice to have


• Proven ability to translate technical issues into understandable language for end-users.


• Willingness to learn new systems and vendors, as needed


• Ability to lift hardware devices, i.e., servers, routers, and switches


• Able to write clear documentation for internal and client use


• Accountability: Holds self and others accountable to meet commitments


• Collaboration and Teamwork: Works with others to deliver results, meaningfully contributing to the team and prioritizing group needs over individual needs.


• Problem Solving: Uses an organized and logical approach to find solutions to complex problems. Looks beyond the obvious to understand the root cause of problems. Knowing when to escalate to other team members for expedited support when needed.


• Open Communication: Clearly conveys thoughts, both written and verbally, listening attentively and asking relevant questions for clarification and understanding.


• Resilience, Tolerance for Change/Ambiguity : Can effectively cope with change, finding ways to advance work and projects.

The Benefits: 

• Variety of employee perks


• Great work culture 


• Access to Rethink’s national DE&I committee and working groups


• Growth and training opportunities

The interviewing process at Rethink:

1. Screen with the Talent Acquisition


2. First round interview with Hiring Manager


3. Second round Interview with IT Infrastructure Manager


4. Third round interview with peer


5. References 


6. Offer 

Office Location: 720 King Street West, Toronto, ON
Vacancy status: This posting is for an existing vacancy
Contract Start: December 1st 2026
Salary: $70K - 75K per year, pending experience, skills, scope of responsibility, internal equity, and business needs.

We truly appreciate everyone’s interest but only those selected for an interview will be contacted. 

Rethink is committed to creating and maintaining an inclusive, equitable and accessible workplace. We welcome and encourage applications from all intersections. Accommodations are available, upon request, to all selected candidates during any stage of the recruitment process.