The roleMaintainX's support stack serves 13,000+ enterprise customers across some of the world's largest industrial operations. As Senior Support Systems Administrator, you're the technical owner of that infrastructure - not just keeping it running, but making it more resilient, more automated, and more trusted as we scale.
You'll act as the technical lead for our Zendesk ecosystem and integrated tooling (n8n, Zapier, Intercom), bridging Support, Sales, Customer Success, Engineering, and Product. Your primary focus is scalability, system resilience, and data integrity - not just day-to-day config.
- Own the Zendesk ecosystem - routing logic, triggers, SLAs, and Contextual Workspaces - so every ticket reaches the right agent without manual intervention.
- Build and maintain reliable 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.
What we're looking forMust-haves:- 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.
Nice-to-haves:- Experience with React or Tailwind CSS for Help Center customization.
- SQL or advanced data visualization experience (Looker, Tableau).
- Previous hands-on or frontline customer support experience.
What we offer- 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.
How we workWe deliver one platform for maintenance, repair & operations teams to keep the physical world running. You'll work alongside smart, humble colleagues across North America who care about getting it right. We're output-driven, promote quickly when people deliver, and have honest conversations early. If that's the environment you want, we'd love to hear from you.
