MaintainX is the world's leading AI-powered maintenance and asset management platform, serving 13,000+ customers including Duracell, Shell, Cintas, and Brenntag. We raised $150M in Series D funding led by Bessemer Venture Partners and Bain Capital Ventures, bringing our total funding to $254M. We were named to the Forbes 2025 Cloud 100, the definitive ranking of the top 100 private cloud companies in the world. We're growing fast and hiring the talent to match. MaintainX is the world’s leading AI-powered maintenance and asset management platform, trusted by 13,000+ customers — including Duracell, Shell, Cintas, DHL, and Brenntag — to keep industrial operations running. Our platform manages 13.9M+ assets and has powered 79.5M+ completed work orders for 150,000+ weekly active technicians worldwide. In July 2025 we closed a $150M Series D led by Bessemer Venture Partners and Bain Capital Ventures, bringing total funding to $254M at a $2.5B valuation. We were named to the 2025 Forbes Cloud 100 and ranked #1 in EAM and CMMS on G2’s Summer 2025 report. The market is moving: 68% of industrial companies have the same or more downtime than in 2024, and 3.8M manufacturing jobs will go unfilled through 2033. We’re building the platform that changes that. The role MaintainX’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 for Must-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 work We 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. MaintainX is committed to creating a diverse environment. All qualified applicants will receive consideration for employment without regard to race, colour, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. Our mission is to deliver one platform for maintenance, repair & operations teams to keep the physical world running. We believe the greatest asset in any organization is the people. That’s why we built an intuitive, mobile-first solution to help boost productivity and collaboration across teams and locations. MaintainX is committed to creating a diverse environment. All qualified applicants will receive consideration for employment without regard to race, colour, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status.