Senior Atlassian Engineer: Jira, Confluence & AI Automation

Oscar; Chicago (IL); Hybrid; USD 150,000 - 200,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

401(k) plan

Discretionary bonus

Hybrid work

Life insurance

Disability coverage

HSA/FSA

Job summary

Oscar, a leading global financial services firm, seeks a Senior Atlassian Engineer in Chicago with deep Jira/JSM/Confluence expertise to own and enhance the Atlassian platform. You will manage migrations, develop custom workflows, and drive automation across ITSM, HR, and enterprise processes.

The role requires 5+ years of hands-on Atlassian experience in enterprise environments, strong scripting and REST API skills, and a collaborative approach with stakeholders.

Qualifications

• 5+ years as Atlassian Engineer, Jira Developer, Jira Administrator, or Atlassian Architect.
• Strong hands-on Jira/JSM/Confluence in enterprise environments.
• Proven experience migrating Jira and Confluence from Data Center to Cloud.
• Experience designing complex JSM/ITSM workflows and HR service workflows.
• Proficient in REST APIs, webhooks, and scripting for integrations.

Responsibilities

• Manage and develop the enterprise Atlassian environment across Jira, JSM, and Confluence.
• Support Data Center to Cloud migrations, including planning, testing, data validation, and cutover.
• Design and build custom Jira workflows, scripting, automation, and platform configurations.
• Develop and optimize JSM service desks, ITSM processes, SLAs, and request management workflows.
• Build HR service workflows including onboarding, offboarding, and employee case management.
• Design and maintain Jira Assets/CMDB structures, integrations, and automation.
• Build integrations between Atlassian and other business applications using REST APIs and webhooks.
• Introduce AI-powered automation using tools such as Atlassian Rovo, Claude, and MCP servers.
• Maintain platform security, governance, performance, and data integrity.
• Collaborate with technical teams, business stakeholders, and external consultants.

Skills

Jira/JSM/Confluence

Data Center to Cloud

Automation scripting

REST APIs

Webhooks

Stakeholder communication

Education

Bachelor's degree in CS/IT or related

Tools

Git

Testing & deployments

Slack/SharePoint integrations

Job description

Oscar, a leading global financial services firm, seeks a Senior Atlassian Engineer in Chicago with deep Jira/JSM/Confluence expertise to own and enhance the Atlassian platform. You will manage migrations, develop custom workflows, and drive automation across ITSM, HR, and enterprise processes.

The role requires 5+ years of hands-on Atlassian experience in enterprise environments, strong scripting and REST API skills, and a collaborative approach with stakeholders.