From Budget Approval to Deployment: Navigating the JSM Migration Journey

Migrating to Atlassian Jira Service Management involves much more than installing new software. It’s a structured journey—from securing budget all the way through deployment and user adoption. This guide takes you through each phase clearly and practically, helping teams plan, align stakeholders, and execute confidently.

1. Securing Budget and Establishing Support

Make the Case with a Clear Business Opportunity

• Quantify total cost of Boron Cherwell: licensing, hosting, scripting/development, incident downtime, and support services.
• Show potential savings for JSM, including agent only licensing, no infrastructure costs (in cloud), and leaner automation.
• Highlight risk management, especially Cherwell end of life timelines and security concerns for unsupported versions.
• Present real examples: other organizations reporting up to 50 % lower ongoing ITSM spend after switching to JSM (without sacrificing performance).

Build Executive and Stakeholder Alignment

• Involve CFO/finance to understand licensing model and ROI.
• Engage IT Operations, HR, Facilities, or Service Desk as early adopters.
• Align on timeline, resourcing, and overall objectives.
• Build a steering committee or oversight group to maintain alignment during the project.

2. Planning and Assessment

Conduct Detail Project Scoping

• Inventory all Cherwell components: request types, workflows, forms, SLAs, automations, integrations, asset types, and dashboards.
• Identify service teams and stakeholders affected.
• Determine compliance and data retention requirements.

Set Goals and Metrics

• Define success: migration timeline, zero downtime, user adoption targets, performance benchmarks, satisfaction scores.
• Include metrics like first-response time, ticket resolution time, portal usage rate, and average SLA performance.

Map Your Target Architecture in JSM

• Set out project structure: separate JSM projects for IT, HR, Facilities, Legal, etc. as needed.
• Build or reuse templates for common ticket types.
• Define automation rules for common use cases: assignment, notifications, escalations, SLAs.
• Plan integrations—IdP, knowledge base (Confluence), Opsgenie, asset system (Assets), DevOps tools.

3. Building a Proof of Concept or Pilot

Choose a Scoped Pilot—Quick Wins First

Focus on a high-volume but low-risk area, such as incident or request management within a single team.

• Set up a staging JSM instance with workflows and automations based on existing Cherwell design.
• Load representative tickets (closed and open) to validate mapping logic and form functionality.
• Invite a small group of agent users and end-users to interact with the new system, submit sample requests, and gather feedback.

Use Feedback to Adjust

• Fine-tune workflows, fields, forms, and automations based on user input.
• Validate permissions, SLA configurations, portal usability, and notification flows.
• Revise as needed before full deployment—this builds confidence and strengthens stakeholder buy-in.

4. Data Migration Planning

Define What Data You Actually Need to Move

• Not every historical ticket needs to migrate; consider keeping older data in an archive for compliance.
• Prioritize open and recently closed tickets, key knowledge articles, and essential asset records.

Choose a Migration Approach

• Manual migration for minimal data (via CSV import).
• Automated migration using third-party tools or custom scripts for larger data sets.
• Hybrid approach—manual for key data, automated for bulk records.

Map Fields and Relationships

• Align Cherwell fields with JSM fields (custom fields where necessary).
• Map request types, SLAs, status values, and priority levels consistently.
• Test migration on a small dataset before committing to full migration.

5. Workflow and Automation Configuration

Rebuild or Simplify Workflows

• Review Cherwell workflows—remove unnecessary complexity.
• Leverage JSM’s native workflow editor for intuitive flow and easy maintenance.
• Incorporate automation rules for repetitive tasks to reduce manual effort.

Test Automation Logic

• Simulate ticket creation and progression.
• Validate triggers, conditions, and actions work as intended.
• Ensure automation does not conflict with SLAs or escalation paths.

6. Integration and Ecosystem Setup

Connect Core Systems

• Identity provider (SSO) for authentication.
• Knowledge base (Confluence) for self-service content.
• Opsgenie for incident management.
• Development tools (Bitbucket, GitHub, Jenkins) for DevOps alignment.
• Asset management (Assets in JSM) for CMDB-like functionality.

Validate Data Flow Between Systems

• Ensure data syncs properly across integrations.
• Confirm user permissions remain consistent across platforms.
• Test failover or error-handling scenarios.

7. User Training and Change Management

Prepare Targeted Training Materials

• Create guides and walkthroughs tailored to agents, requesters, and admins.
• Use videos, documentation, and live demos to cover workflows and portal navigation.

Run Training Sessions

• Schedule interactive sessions for Q&A.
• Encourage feedback and clarify process changes.
• Offer follow-up support during the early adoption phase.

8. Testing and Quality Assurance

Conduct End-to-End Testing

• Submit sample requests through the portal and verify processing.
• Test SLA compliance tracking and escalation rules.
• Validate email notifications and integration responses.

Get Stakeholder Sign-Off

• Review test results with the steering committee.
• Ensure all critical functionality meets acceptance criteria before go-live.

9. Go-Live and Monitoring

Plan Your Go-Live Strategy

• Pick a low-traffic period to minimize disruption.
• Communicate the timeline and expectations to all users.
• Ensure support staff are on standby for immediate troubleshooting.

Monitor Early Usage

• Track ticket volumes, SLA adherence, and portal usage metrics.
• Address any reported issues quickly.
• Collect feedback for ongoing improvement.

10. Post-Go-Live Optimization

Refine Based on Real-World Usage

• Adjust workflows, automations, and request types based on adoption trends.
• Update the knowledge base with new FAQs and guides.

Review ROI and Success Metrics

• Compare pre- and post-migration performance indicators.
• Report cost savings, productivity gains, and improved user satisfaction to stakeholders.

📧 Contact us at sales@clovity.com or visit 🌐 atlassian.clovity.com to get started today.