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About the Role

As Senior Support Systems Administrator, you are the technical owner of MaintainX's support infrastructure, responsible for its resilience, automation, and scalability. You will act as the technical lead for the Zendesk ecosystem and integrated tooling, focusing on scalability, system resilience, and data integrity.

Responsibilities

• Own the Zendesk ecosystem, including routing logic, triggers, SLAs, and Contextual Workspaces.
• Build and maintain reliable integrations across Zendesk Suite, ZIS, Intercom, n8n, and Zapier.
• Define and execute QA for all system changes, including test plans, UAT, staging environments, and regression testing.
• Design and maintain disaster recovery for the support infrastructure.
• Own technical documentation for workflows, API dependencies, and system changes.
• Build dashboards to reflect reality, standardize metric definitions, and provide leadership visibility into support performance.

Requirements

• 5+ years in Support Operations, Systems Analysis, or a technical ops role at a SaaS company.
• Deep Zendesk expertise, including 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.
• Experience with React or Tailwind CSS for Help Center customization (Nice-to-have).
• SQL or advanced data visualization experience (Looker, Tableau) (Nice-to-have).
• Previous hands-on or frontline customer support experience (Nice-to-have).

Skills

• Zendesk
• JSON
• JavaScript
• n8n
• Zapier
• QA
• Disaster Recovery Planning
• React
• Tailwind CSS
• SQL
• Looker
• Tableau

Location

• Toronto

Work Type

• Hybrid

Experience Level

• Senior

Salary/Compensations

• Competitive base + variable comp aligned to role and location.

Benefits

• Meaningful equity in a post-Series D, $2.5B company.
• Day-1 health, dental, and vision coverage (Canada Life).
• Unlimited PTO
• $500 home office stipend
• $1K annual L&D budget.

About the Company

• MaintainX is the world’s leading AI-powered maintenance and asset management platform, trusted by 13,000+ customers.
• 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.
• We’re building the platform that addresses the market need for industrial companies to reduce downtime and fill manufacturing jobs.

Equal Opportunity

• 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.