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Transform Cherwell to Jira Service Management: Guidance for a Successful Journey

Co-authored by StrataCom, a leading IT Service Management (ITSM) firm specializing in professional services and consulting, and Atlassian experts.
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IT Service Management (ITSM) software acquisitions, end-of-life scenarios, and evolving internal standards mean enterprise companies may find themselves needing to migrate to a new ITSM solution.
In October 2023, Cherwell enterprise Service Management customers faced this very scenario when software company Ivanti announced the end of life for Cherwell Service Management. Most former Cherwell customers — like many enterprise organizations — need more than just an ITSM replacement. They need a solution that can also help them manage workflows from departments like facilities, HR, legal, security incident ticketing, medical device ticketing, and more. Jira Service Management from Atlassian is an ideal replacement system for Cherwell customers and other users needing a dynamic ITSM solution.
Jira Service Management, a web-based application supported by Atlassian's robust cloud infrastructure, can accommodate organizations of all sizes. It provides a reliable platform that scales with your business growth, ensuring efficient operations. Compared to Cherwell, Jira Service Management offers faster record retrievals and a more responsive interface. The platform distinguishes itself with its superior out-of-the-box workflow capability, facilitating the creation of new workflows for both ITSM and non-ITSM teams such as facilities, HR, legal, and more. Jira Service Management enhances your administrator’s efficiency by centralizing the editing of fields, screens, and workflows and provides a single location for all object workflow rules. The Jira Marketplace boasts thousands of applications that enhance Jira Software and Jira Service Management's functionality.
In what follows, we will explore the key stages of a successful transformation scenario using the transformation from Cherwell to Jira Service Management as an example. We will also highlight important migration considerations.

Three stages of a transformation journey

Transitioning from one ITSM tool to another opens up a world of opportunities for growth and improvement, but it also requires thoughtful discussion and thorough discovery. We've identified three critical stages of a migration:

1. Assess

Conduct a workshop to evaluate your readiness for migration. The impact of a migration extends beyond the tool itself and affects real people and processes, so a comprehensive focus on all business areas that will be impacted is essential.
Important issues to address in your workshop.

2. Mobilize

Create a migration strategy, refine your business case, and finalize your solution design and deployment plan. Address any readiness gaps you identified during the assessment phase. Then, focus on setting up your baseline environment — or landing zone — ensuring operational readiness, and developing cloud skills.
This phase also kickstarts your organizational transformation preparations.

3. Transform and modernize

Begin your transition to a new ITSM environment, such as Jira Service Management. Here you have an opportunity to truly transform your ITSM workflows, rather than simply "lifting and shifting" from one product to another.
The transformation process involves the following important steps:
  • Implementation of the design document
  • Execution of the migration plan
  • Construction of the environment in a phased approach
  • Empowerment of your teams on the new platform
We'll explore this process ini detail below by demonstrating how to the transform from Cherwell to Jira Service Management.

Transforming from Cherwell to Jira Service Management

We will comprehensively address each aspect of the transformation process and common pain points Cherwell customers see in their transformation process.

Elements of an issue

This diagram illustrates the correlation between elements of an incident in Cherwell and elements of an issue in Jira Service Management. As you transition your processes to Jira Service Management, you'll have the opportunity to transform your current processes and more effectively structure your service catalog.
Incident - issue

Tool feature comparison

The following table comprehensively compares Cherwell's features with their corresponding features in Jira Service Management and explains the transition between the two platforms:
Jira Service Management
Reference information
No comparative feature
Projects in Jira Service Management are a container/bucket of Jira issues
Business object
Issue type
Asset object schema - services object
A service catalog is a documented list of services a team offers its customers. These services can be documented in the Assets module
Category & subcategory
Request types
Specifics forms
Configuration items
Asset object records in object schemas
One-steps & automation processes
Automation rules
Lookup table
Object schema

Common hurdles with Cherwell migration

1. Specifics forms transform to forms in Jira Service Management.
See more
Three significant advantages to Jira Service Management forms.
2. One-steps and automation processes transform to automation rules in Jira Service Management.
See more
3. Lookup tables transform into object schemas in Jira Service Management.
See more

Data migration

Data migration in the context of an ITSM tool is a complex process that involves transferring necessary data from an existing ITSM tool to a new one to improve the quality of data in the new system. It's important to note that customers don’t need to migrate all the data. The focus should be on migrating necessary information, as ITSM tools tend to be data-heavy. Conversations around data migration should focus on the following:
What types of data require migration? Data may encompass user data, configuration items (CIs) and assets, knowledge articles, data catalogs (like lookup tables), and pre-existing data records from the legacy ITSM tool, such as incidents, change requests, problems, etc.
How will the data be migrated? As a best practice, any data integrated into your legacy ITSM tool from another source should instead be redirected and reimported into Jira Service Management. Common examples of integrations to redirect include user data and configuration item data. Data housed and maintained in your legacy ITSM tool should be evaluated for its necessity and accuracy. Complex decisions regarding integrations should be addressed during the solution design workshop in the assessment phase of the transformation process. 
How will the data be mapped in Jira Service Management? You'll need to map data you're migrating into the new ITSM tool. Adopting a new operational approach with Jira Service Management may introduce complexities in your data migration considerations. During a solution design discussion, you'll need to discuss how data points in your legacy ITSM tool correspond to those in Jira Service Management. Consider alternative strategies, such as migrating historical data into a separate data warehouse, creating a distinct Jira Service Management project for historical data to preserve its integrity as in the legacy tool, or remapping the historical data to align with the new Jira Service Management architecture.

Tools for migrating data from Cherwell to Jira Service Management

Using a tool like StrataCom’s Cherwell to Jira Service Management migration toolkit can help speed up the transformation process by allowing you to map fields and let the migration tool handle the data migration, including updates, journal entries, creating related items like tasks, and more.
The diagram below is a visual representation of how the Stratacom migration tool transforms data from Cherwell into Jira Service Management:
stratcom migration tool
Your next decision will concern the volume of data you intend to transfer from Cherwell to Jira Service Management. We commonly observe three migration scenarios that need to be addressed for Cherwell customers transitioning to Jira Service Management:
  • Only Open tickets
See more
  • Open tickets and recent history tickets
    See more
  • All open and historical tickets
    See more
The transformation journey to a new ITSM platform is not just about migrating ITSM tools; it's about embracing a modern approach to enhance your organization's service management practices and unlock possibilities for innovation and growth.
As you're deciding which new platform to choose, reflect on what modernization means for your organization. Then, consider how a platform like Jira Service Management can support your digital transformation initiatives and goals.
More about StrataCom:
We cater to mid-market and enterprise-level clients, offering elegant solutions that bridge the gap between vision and reality. With decades of hands-on experience in IT Service Management, we go beyond mere technical assistance to become your dedicated partner and trusted advisor. Our team, comprised of senior-level ITIL certified consultants, possesses deep expertise in the IT Service Management domain. We excel in translating complex technological visions into actionable strategies, ensuring our clients' ongoing success. At StrataCom, we are committed to delivering the care, expertise, and core knowledge essential for your IT Service Management needs.

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