Senior Atlassian Engineer

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

Location: Chicago, IL (Hybrid - 3 days onsite per week)

Employment Type: Full-Time, Permanent

Salary: $150,000 - $200,000 Base + Annual Discretionary Bonus

About the Opportunity

We are partnering with a leading global financial services firm in Chicago that is looking for a Senior Atlassian Engineer to join its technology team.

This is a hands-on engineering role focused on developing, managing, and improving the company's Atlassian environment, including Jira, Jira Service Management (JSM), and Confluence.

The successful candidate will take ownership of the platform, support a major Data Center to Cloud migration, develop custom workflows and integrations, and help introduce AI-driven automation across the business.

Key Responsibilities

• Manage and develop the enterprise Atlassian environment across Jira, JSM, and Confluence.
• Support Jira and Confluence 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 management workflows, including onboarding, offboarding, access requests, 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, webhooks, and scripting.
• Introduce AI-powered automation using tools such as Atlassian Rovo, Claude, and MCP servers.
• Maintain platform security, governance, performance, and data integrity.
• Work closely with technical teams, business stakeholders, and external consultants to deliver platform improvements.

Required Skills & Experience

• 5+ years of experience as an Atlassian Engineer, Jira Developer, Jira Administrator, or Atlassian Architect.
• Strong hands-on experience with Jira, Jira Service Management (JSM), and Confluence in enterprise environments.
• Proven experience migrating Jira and Confluence from Data Center to Cloud.
• Strong Jira development skills, including custom workflows, scripting, and automation.
• Experience designing and implementing complex JSM and ITSM workflows.
• Experience building enterprise service workflows, including HR onboarding, offboarding, and employee service requests.
• Experience developing integrations using REST APIs, webhooks, or middleware.
• Experience with Git, testing, change management, and controlled production deployments.
• Strong communication skills and the ability to work directly with technical and non-technical stakeholders.
• Bachelor's degree in Computer Science, Information Technology, or a related field, or equivalent experience.

Nice to Have

• Experience with Jira Assets/CMDB, including object schemas, imports, and integrations.
• Experience with Atlassian Rovo, Claude, MCP servers, or AI-driven workflow automation.
• Experience integrating Atlassian with Slack, SharePoint, HR platforms, or identity management systems.
• Background working within financial services or another regulated industry.
• Atlassian certifications such as ACP-120, ACP-620, or ACP-420.
• Base Salary: $150,000 - $200,000, depending on experience.
• Bonus: Annual discretionary performance bonus.
• Location: Chicago, IL - Hybrid (3 days onsite).
• Comprehensive medical, dental, and vision insurance.
• 401(k) with discretionary employer contributions.
• Life insurance and short- and long-term disability coverage.
• Health savings and flexible spending accounts.

Why Consider This Opportunity?

This is an opportunity to join a well-established, technology-driven financial services organization where engineering plays a key role in business operations.

You’ll have the chance to take ownership of a large-scale Atlassian platform, contribute to Cloud modernization projects, and introduce new automation and AI capabilities.

The role offers a combination of hands-on technical engineering, platform ownership, and long-term career development within a collaborative technology team.