Senior Support Systems Administrator

📋 Description

• Own the Zendesk ecosystem — routing logic, triggers, SLAs, and Contextual Workspaces — so every ticket reaches the right agent without manual intervention.
• Build and maintain integrations across Zendesk Suite, ZIS, Intercom, n8n, and Zapier; own the middleware layer that connects our support stack.
• Define and execute QA for all system changes: test plans, UAT, staging environments, and regression testing before anything reaches production.
• Design and maintain disaster recovery for the support infrastructure — organized backups, recovery runbooks, and incident lead when things break.
• Own technical documentation: a version-controlled source of truth for all workflows, API dependencies, and system changes — accurate enough for engineers, clear enough for agents.
• Build dashboards that reflect reality, standardize metric definitions, and give leadership trusted visibility into support performance.

🎯 Requirements

• 5+ years in Support Operations, Systems Analysis, or a technical ops role at a SaaS company.
• Deep Zendesk expertise — triggers, automations, Liquid Markup, API usage, and Contextual Workspaces.
• Technical fluency in JSON and JavaScript; hands-on experience with n8n or Zapier for middleware automation.
• Proven QA discipline: test case creation, staging environments, regression testing, and UAT execution.
• Track record of writing documentation that engineers trust and support agents can follow.
• Experience with backup strategies and disaster recovery planning for SaaS tooling.

🎁 Benefits

• Competitive base + variable comp aligned to role and location.
• Meaningful equity in a post-Series D, $2.5B company.
• Day-1 health, dental, and vision coverage (Canada Life).
• Unlimited PTO — not a gimmick; we take it.
• $500 home office stipend · $1K annual L&D budget.
• Toronto hub with flexible hybrid setup.