Freelance Jira Configuration Specialist
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Flexible Schedule
Freelance
We’re building Telos, an AI assistant for Atlassian consultants that automates Jira and Jira Service Management (JSM) configuration work. It already handles many standard administration tasks, but its real power comes from skills — reusable packages of expert knowledge that teach the assistant how to handle specific configurations, edge cases, and best practices.
We’re looking for a hands-on Jira expert to evaluate what the assistant can do today, identify gaps in its knowledge, and help expand its capabilities by turning their expertise into skills the assistant can learn from. Think of it as a mix of testing, problem-solving, and knowledge transfer.
*This is a freelance position. Standard Railsware benefits do not apply
Your skills
- Strong hands-on Jira and JSM administration experience across a variety of real-world scenarios
- Deep understanding of configuration approaches and best practices, with the ability to explain trade-offs between different solutions
- Comfortable working with AI tools and interested in helping improve AI systems through structured knowledge
- Strong attention to detail and a systematic approach to testing and documentation
Nice to have
- Experience in teaching AI systems through structured knowledge and reusable skills
Your responsibilities
- Test Jira and JSM configurations with the assistant — workflows, schemes, custom fields, permissions, automation, SLAs, request types, and more. Document what works correctly, what is missing, and where improvements are needed
- Map coverage and gaps — maintain a clear record of supported use cases and areas where the assistant's recommendations diverge from best practices
- Convert Jira expertise into skills — capture your knowledge as structured, reusable instructions, decision logic, configuration patterns, and rationale. Templates will be provided; no AI background is required
- Validate newly created skills — re-test scenarios to confirm the assistant can successfully handle them
- Document edge cases and best practices — identify situations where multiple valid approaches exist and explain the trade-offs
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