Senior IT Specialist

About Dialogue

Dialogue is the #1 virtual care provider in Canada. By developing our Integrated Health Platform🅫, we provide exceptional online health and wellness programs (primary care, mental health, iCBT, EAP, and wellness) to organizations that want to improve the wellness of their employees and families.

When it comes to our work, we set the bar high. Together, we’re transforming health and helping millions improve their well-being. We’re firm believers that great people don’t settle on:

• Impact
• Community
• Growth
• Excellence

Feel like you can make a difference? Good news, we saved you a seat!

Come as you are. As a proud equal-opportunity employer, Dialogue is dedicated to creating a diverse and inclusive workplace for everyone. Qualified applicants will be considered regardless of citizenship, ethnicity, race, colour, religion, gender, gender identity or expression, sexual orientation, disability, age, or veteran status. Applicants who require specialized accommodation are encouraged to contact .

AI Disclosure Statement

To ensure an efficient and fair review process, we utilize artificial intelligence tools to assist in the initial screening and assessment of applicants for this role.

Your role as a Senior IT Specialist

Reporting to the Manager, IT Operations & Security, the Senior IT Specialist runs core IT operations and supports security, identity, device management, and infrastructure work. You’ll handle senior escalations, drive operational improvements, and lead projects that improve how employees access systems, devices, and corporate services.

What you'll be doing

• Provide Level 2/3 support across hardware, software, SaaS, identity, network, and endpoint issues in a macOS-first environment.
• Lead IT projects end-to-end: discovery, stakeholder alignment, implementation, documentation, change management, and post-launch support.
• Define scope, timelines, and success metrics; track risks/dependencies; coordinate delivery with internal teams and vendors.
• Administer Okta, Google Workspace, and SaaS apps through admin consoles and infrastructure-as-code (e.g., Terraform).
• Support device management and endpoint workflows in our MDM, and build automations to cut down on manual work.
• Improve IT service delivery and operational workflows, including integrations between systems and tools.
• Act as a senior escalation point for the team and help guide technical decisions.

We'd love to hear from you if you have

• 5+ years in IT operations, technical support, endpoint management, and/or a security-adjacent role.
• Strong experience supporting macOS fleets and corporate SaaS apps.
• Scripting experience and familiarity with programming languages.
• Comfort with cloud fundamentals (AWS/GCP/Azure), including networking and access concepts.
• Experience with an MDM platform (e.g., Iru or Jamf).
• Experience with infrastructure-as-code for SaaS/identity (e.g., Terraform).

At Dialogue, your well-being is our priority

Taking care of others also means taking care of our team! Depending on your role and employment status, you could have access to the following benefits:

• Access to the Dialogue app and virtual mental health support for you and your family
• Fully funded insurance, a health spending account, dental coverage, and fitness reimbursement
• 4 weeks vacation, 9 wellness days, and 1 volunteer day
• Hybrid work: 3 days/week in our Montreal office, excluding remote roles
• Work abroad up to 4 weeks/year
• Incentive plans, referral bonuses & RRSP matching
• Learning via Coursera, external training budget & mentorship
• Optional parental leave top-up

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