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Sr. Atlassian Jira Administrator
Toronto, Ontario, Canada
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Position Title: Sr. Atlassian Jira Administrator

Department: Global Technology Services

Location: Hybrid / Remote (2 days per week - eventually 4 days/week)

Length: N/A

Type: Full-Time Contract

Job Overview: We are seeking a Sr. Atlassian Jira Administrator whose primary mandate is to lead and execute our enterprise-scale migration from Jira Data Center to Jira Cloud. In this role, your absolute main function will be designing the migration strategy, managing the data transition, and ensuring a seamless, zero-downtime cutover for thousands of users. This position focuses heavily on utilizing the Jira Cloud Migration Assistant (JCMA), analyzing complex on-premise legacy data, resolving third-party app compatibility for the cloud environment, and rebuilding customized workflows to operate flawlessly in Atlassian’s SaaS infrastructure.


Key Responsibilities

  • Core Migration Execution: Serve as the technical lead responsible for the end-to-end migration of massive, complex Jira instances from on-premise Data Center directly into Atlassian Cloud.
  • Data Transfer & Hygiene: Utilize the Jira Cloud Migration Assistant (JCMA) and site import tools to execute secure data transfers, ensuring complete data integrity, mapping, and cleanup prior to the move.
  • App & Plugin Resolution: Audit all existing Data Center Marketplace apps, identify their Cloud equivalents, coordinate vendor data migration, and engineer workarounds for plugins that do not exist in the Cloud.
  • Workflow Customization & Scripting: Write and deploy custom scripts (using Groovy or ScriptRunner) to adapt, fix, or rebuild legacy workflows and custom fields for the new Cloud architecture.
  • Testing & Cutover Management: Build Cloud sandboxes for rigorous User Acceptance Testing (UAT), develop detailed migration runbooks, and execute the final production cutover over scheduled weekends to ensure zero business disruption.
  • Security & Cloud Admin: Configure Atlassian Guard for Cloud SSO/Active Directory integration to meet bank-level security standards, and provide post-migration administrative hypercare to users.


Required Skills & Qualifications

  • Migration Expertise: Proven, hands-on experience as the primary technical lead executing large-scale Jira Data Center to Jira Cloud migrations (this is a strict requirement).
  • Migration Tools: Deep expertise with Atlassian's official migration tools, specifically JCMA (Jira Cloud Migration Assistant) and cloud sandbox environments.
  • Scripting & Automation: Strong proficiency in Groovy, ScriptRunner, or REST APIs, specifically utilized for transforming on-premise data and automating cloud workflows.
  • App Ecosystem: Extensive knowledge of the Atlassian Marketplace and the technical challenges of migrating complex third-party apps (e.g., Zephyr, Xray, Structure) from Data Center to Cloud.
  • Security & Identity: Solid grasp of Atlassian Guard, enterprise SSO, Active Directory integration, and cloud security compliance within a financial or highly regulated setting.
  • System Architecture: Deep understanding of complex permission schemes, workflow conditions, and data structures at a massive enterprise scale (1,000+ users).
  • Experience: 5+ years of senior-level Jira administration experience, with a heavy emphasis on enterprise infrastructure upgrades and cloud transitions.



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