Migrating to the cloud doesn’t have to feel like navigating a storm. Every digital transformation initiative is unique and comes with its own risks, surprises and decisions that can make or break your journey — but it doesn’t have to be overwhelming.
Anthony Jimenez
Welcome back to CarahCast, the podcast from Carahsoft, a trusted government IT solutions provider. Subscribe to get the latest technology updates in the public sector. I'm Anthony Jimenez, your host from the Kerasoft production team.
On behalf of Atlassian, we would like to welcome you to today's podcast, focused around migrating to the cloud. Hertzam's Ruslan Slain, Vice President of Delivery in the Americas, and Carahsoft's Nicole Coughlin, Atlassian team manager, will discuss the primary risks of infrastructure modernization and explores how to turn a high-pressure digital transformation into a clear skies success story.
Nicole Coughlin
Hello, friends. Welcome to our podcast today. We will talk with Ruslan Slain, who is the VP of Delivery at Hertzam, which is a part of Catworks, about the risks of migrating to the Atlassian cloud and how you can mitigate them.
Welcome, Rus. Can you please tell us a little bit about yourself and your job at Hertzam?
Ruslain Shlain
Hello. Thank you for having me. I'm glad to be here.
So my experience kind of goes back a ways. I started out in the early days of .com as a developer, kind of progressed from there, and at some point, kind of landed in the Atlassian ecosystem. That probably goes back 14 years, if I remember it correctly, and I'd like to brag that I've been to about 10 Atlassian summits, or they call them teams now.
And so I joined Hertzam back when it was Hertzam as a principal consultant and kind of ended up in a role of director over time. And then as recent as July 2025, Hertzam was purchased by Catworks, and so we are now part of the Catworks, and I head up the Americas delivery team as a VP of delivery. And so kind of in my past and recently, I've been involved in many migrations, kind of overseeing it at the high level and as well as hands-on and migrated systems as of late, obviously, the Atlassian on-prem to the Atlassian Cloud, but beyond that, I've seen migrations from different systems of different sorts from, you know, ADO to Atlassian Cloud and vice versa, same with ServiceNow and so on.
So a lot of experience, a lot of depth in the migration work.
Nicole Coughlin
Thank you, Russ, and thank you so much for joining us today. Russ, what are the main risks a company faces during a migration process to the Atlassian Cloud?
Ruslain Shlain
The risks really depend on how prepared companies are going to be going into the migration. Here are the main ones that we see. Data loss corruption is the number one risk.
Companies have years, sometimes decades of historical data, including work logs, attachments, custom fields and workflows. If the migration isn't properly planned and tested, things can get lost in transition. We always tell clients to test, test and test again in a sandbox environment before going live.
Another one is a business disruption. That's the second major risk. Many companies underestimate how long their teams will be offline or working in degraded states during the cutover.
And so without strategic timing and communication, hundreds or thousands of users can suddenly lose access to critical workflows. We've seen companies attempt migrations during their busiest periods, which is a recipe for disaster. Another one is app compatibility.
That's another huge risk. Companies might have 20 to 30 apps in their data center instance, and not all of them have cloud equivalents or work in the same way in the cloud. So we spend significant time during discovery figuring out which apps are mission critical and whether cloud alternatives exist or if processes need to be rethought entirely.
A big one also is change management. It's probably the most underestimated risk. The cloud works differently.
Permissions models are different. Admin capabilities are different. And performance characteristics are different.
Without proper preparation, teams experience resistance and frustration post-migration. Another big one is insufficient planning. It is really a root cause of most migration failures.
Companies often want to migrate in 30 days without even completing a proper inventory of their instance. They don't know what apps they're using, who the stakeholders are, or what their success criteria looks like. And so without upfront planning, everything else kind of falls apart.
Another one we see often is errors identifying all items to migrate. And it happens frequently. Companies forget about archive projects or don't realize they have integrations running through the webhooks or APIs to other systems.
Then mid-migration, something breaks in the downstream system, and everyone scrambles, and everything kind of goes sideways. We have a whole discovery phase where we map out everything before even discussing migration timelines. An experienced in migration process is a major factor as well.
Many IT teams are incredibly talented, but they have only done one or two migrations in their entire career. Meanwhile, migration specialists are doing these every month. There are numerous nuances around using permission transitions, custom integrations handling, and sequencing dependencies between instances.
And so experience does matter. Ignorance of best practices. They appear when companies try to lift and shift approach, wanting to create a data center instance exactly in the cloud.
This isn't always the right approach. Cloud has different capabilities and constraints, and sometimes the best practice is to simplify and modernize rather than just migrating technical debt. And then last but not least is resistance to change.
This is a silent killer of migrations. You can have a technically perfect migration, but without user adoption, it will fail. Migration is 30% technical and 70% people.
You need champions training and clear communication about the benefits.
Nicole Coughlin
Great, thank you. In your experience, which of them is the most common and harmful?
Ruslain Shlain
I would say insufficient planning is both the most common and most harmful because it's the gateway to all other problems. When company does not plan properly upfront, that's when they miss items during the discovery. Don't allocate enough time for change management and underestimate complexity while trying to proceed without experience help.
Organizations often come to us after starting a migration on their own that has gone sideways. Postmortems are always traced back to inadequate planning in the beginning. They don't do proper current state assessments, define clear success criteria, and build in buffer time or identify all the stakeholders.
The insufficient planning feels like saving time in the short term. Let's just get started. We'll figure out everything else along the way mentality.
But what actually happens is making decisions on the fly, discovering problems mid-migration when they're 10 times more expensive to fix and burning through goodwill with users because things keep breaking or changing unexpectedly. The recommendation for this is invest time upfront in planning. Spend extra months really understanding your environment, map dependencies, build runbooks, and prepare communication strategy.
Once migration kicks off, momentum takes over, and course correction becomes very difficult. Companies that do it right spend 40 or 50 percent of their project timeline in planning and preparation phases. If actual migrations go smoothly, users are happy and they hit go-live dates on time.
And it's night and date compared to those who are rushing.
Nicole Coughlin
Thank you. Atlassian recommends working with a certified partner during the migration process. Why should HRSM be chosen?
Ruslain Shlain
So Atlassian recommends working with a certified partner during migration. And here's what makes HRSM different. So our deep experience and expertise.
HRSM has 20 years of experience working with Atlassian products and their personalization. We're not newcomers. We've been in the ecosystem since the early days, witnessing evolution from standalone user installations to massive enterprise deployments through every version and major platform shift.
That depth means that we've seen it all and know how to navigate complexity. We have a premium partner status. We are an Atlassian Platinum solution partner, a highest tier achievable.
As a part of the Catworks group, we have scale and resources across multiple markets. Working with HRSM means accessing a global network of expertise, not just local consultancy. When we do have a certified global team, we do have a group of certified Atlassian cloud experts supporting companies around the world in their migration processes.
These aren't just people who pass certification exams. They are practitioners actively supporting migrations daily. They understand nuances across different industries, regulatory environments, and organizational structures.
Whether you're in financial services with strict compliance requirements or manufacturing with complex DevOps pipelines, we have people who have done similar migrations. We do have comprehensive services. We provide services across the entire Atlassian ecosystem, including cloud migrations, ITSM consulting, Jira service management implementations, DevOps transformations, and custom app development.
When planning your migration, we think holistically about optimizing your entire Atlassian environment, not just moving boxes from point A to point B. We have the resources and expertise to make your company's Atlassian cloud migration process a success. The initial assessment through planning, execution, and post-migration support, we are with you all the way.
We can scale our team to meet your needs with established playbooks and methodologies refined over hundreds of migrations. Migrations to Atlassian cloud is a significant undertaking, which should not be taken lightly, as I mentioned earlier. You want a partner who's been there, who has the expertise and the resources to make those migrations successful.
And we do have kind of round-the-clock support, and people are available not to only support you through the migration process, but also post-migration.
Nicole Coughlin
Thank you. And, Russ, can a migration process be agile?
Ruslain Shlain
Absolutely, yes. In fact, migration processes should be agile. When people think about migrations, they often default to the traditional waterfall mindset, with big upfront planning, kind of rigid timelines, and everything locked down before starting.
While planning is critical, execution doesn't have to be rigid and inflexible. You'll discover things during the process that you didn't anticipate. The integrations are behaving differently in cloud environments, workflows that need adjustments, or data quality issues.
In rigid plans, discoveries become a crisis. In agile approaches, they're part of a normal iterational cycle. Breaking migrations into smaller, manageable chunks, instead of trying to migrate everything at once, right?
That's one of the big things that we preach. Sprint might migrate, you know, sprint one might migrate a pilot project with one team, sprint two may handle another set of projects, and so on. Each sprint will have its clear goals, deliverables, and success criteria.
And then each sprint with risk perspective to identify what worked, what didn't, and what needs adjustment. Right, we work with business to understand which processes, which projects or teams are most critical, most complex, or would benefit most from moving first. Adjust prioritization as you learn more.
If you discover team A needs to be there before team B, due to unseeded dependency, agile approach allows that to happen, right? You can pivot. After each migration phase, gather the feedback from users, admins, and stakeholders about what's working, what's causing pain, and what needs refinement.
We incorporate that feedback into the next phase for continuous improvement, rather than just launch and pray. Rather than waiting six months to deliver everything at once, teams starting to get cloud benefits as soon as their migration completes. Faster performance, better collaboration features, automatic updates, and so on.
Early value builds momentum and support for remaining migration phases. And then you're also able to maintain flexibility. If a planned cloud app doesn't meet needs during testing, agile migrations allow exploring alternatives, adjusting approaches, or rethinking the process that app was supporting.
We're not locked into decisions made months ago. Being agile doesn't mean being chaotic or unprepared. You still need solid upfront assessment and planning phases, clear governance, defined roles, and risk management.
But execution can absolutely be agile. And then you do get results and benefits of that. Migration run with agile methodologies tend to have higher success rates.
Better user satisfaction, fewer crap moments. You're learning and adapting through the process, rather than discovering all problems at the end. Plus, most clients are already using JIRA and agile methodologies for their own work.
And so running the migration as an agile project just makes sense, and it's not new to them. They're practicing what we preach and using the very tools we're migrating to manage the migration itself. And so bottom line, not only can migration be agile, it absolutely should be.
Nicole Coughlin
And Ross, when do you think a company should start its migration process?
Ruslain Shlain
That's a great question. Honest answer is yesterday, but here's a realistic answer. So let's talk about the timeline reality.
We have the March 2029 end of life deadline for license data center. So that sounds far away. But when you factor in actual migration timelines, the window is tighter than people think.
At last thing is published guidance. That's an eye-opening, right? So for clients with 10,000 users or more, migration could take up to 18 months.
Clients with 5,000 plus users, process can take approximately six months. And then clients with 1,000 users, you're looking at about three to six months for migration. And that assumes that everything goes smooth as butter.
But you got to remember that every company is different. And so there are estimates that are less than provided. But the reality varies by company.
Some have complex integrations, heavy customized workflows, numerous apps, and regulatory requirements. Other are more straightforward. That's why we recommend starting with phase zero, the discovery and assessment phase.
It helps you to analyze your specific situation, your infrastructure, and complexity to provide a realistic timeline for your migration. Not just kind of generic estimates. Even with shorter timelines, you got to account for budget cycles, resource availability, testing periods, and change management.
Waiting until 2027 or 2028 creates a tough situation with the timelines that are going to be so rushed. Competition for a partner resources as everyone else is going to be in panic mode as well. And you're not going to have the luxury to do it right.
And so even if starting just means doing an initial assessment or understand where you stand, that's okay. Maybe you'll discover that you can take a phased approach, spreading migrations over multiple quarters. Maybe you'll find a technical debt that needs to be addressed before you're even ready to migrate.
Before you know it, the 12 months are going to come and go. We've seen companies starting migrations planning now. And they have to work through all the steps that I mentioned.
And they learn in the early phases. And they properly train and prepare teams so they're not in the crisis mode later. We do have flexible engagement models.
We offer several assistance models for migration process depending on where you are in your journey. We support the initial phases. So we can start with just an assessment, kind of give you a guidance of where you need to go with this.
We do have a fixed price packages, got a full to end to end managed services with clear scope and costs, as well as a custom tailor engagements, right? So match your specific needs and budget. And so don't wait, you know, reach out for a conversation.
Even if you're not ready to kick off on migration today, let's do an assessment. So you'll know what you're dealing with. Contact us and we'll help you define the best journey to the cloud for your company.
One that fits the timeline, the budget and specific requirements.
Nicole Coughlin
Thank you for taking your time to speak with us today, Ruslan. We enjoyed hearing from you on the ways Herzem and Atlassian can be involved in the migration journey.
Anthony Jimenez
Thanks for listening. And thank you to our guest, Ruslan. Don't forget to like, comment and subscribe to Carahcast.
And be sure to listen to our other discussions. If you'd like more information on how Atlassian can assist your organization, please visit www.carasoft.com slash Atlassian or email us at Atlassian at carasoft.com. Thanks again for listening and have a great day.