CloudBees CEO: Why Migration Is a Mirage Costing You Millions
A recent survey shows that, last year, 57% of enterprise organizations spent over $1 million on migration projects — with an average loss of $315,000 per project due to unexpected overruns — in pursuit of what Anuj Kapur, CEO of CloudBees, calls “the migration mirage.”
In this episode of The New Stack Makers, Kapur sat down with TNS Founder and Publisher Alex Williams to discuss the findings from the CloudBees “2025 DevOps Migration Index” report. Published in November, it’s the first survey of its kind to quantify the pain (and the often-elusive rewards) of trying to achieve modernization through migration, and why the result has organizations chasing a future that keeps receding.
The Hazards of Underestimating System Longevity
Technical leaders are under constant pressure to move faster, adopt AI and modernize aging systems. Unfortunately, many decide to replace everything with one consolidated platform while underestimating just how resilient and valuable their existing infrastructure actually is.
“The half-life of an enterprise application is probably five times the half-life of an enterprise CIO,” Kapur said. “CIOs come and go, applications don’t.“
As a result, he said, organizations underestimate the longevity of their systems and the resiliency of the infrastructure that exists to actually support them. Executives come and go while that decades-old legacy system just keeps running — until, that is, new leadership arrives with new modernization mandates.
“Modernization is very essential in both the IT tier and the application tier, but the problem is we have come to equate modernization with migration,” Kapur continued.
Modernization vs. Migration: A Critical Distinction
The “DevOps Migration Index” report is the first quantitative assessment of the reality that, for most organizations, modernization and migration are the same thing.
“Migration takes longer, costs more and basically pushes you backward,” Kapur said. “The resources that you should spend on customer requirements are instead spent on replatforming and restructuring your IT environment to be able to deliver value at some unknown point in the future.”
He calls this “the migration mirage.”
The Human Capital Costs of Migration
Beyond financial costs, migration also carries human capital costs in the form of developer morale. “Engineers want to build things. They want to be in front of customers. They want to drive value,” Kapur said. “What they don’t want to do is fundamentally change systems that are actually working and delivering value.”
Rather than pushing customers toward a single platform, toolchain or even architecture, CloudBees advocates for meeting developers where they are.
“Telling developers what tools to use is like telling teenagers what to wear,” Kapur said. “If you’re empowering developers to build, if you believe that they’re the focal point of the transformation, then you need to treat them like adults.”
The full conversation goes deeper into how organizations can set guardrails without stifling creativity, what the emergence of code assistance tools means for the outer loop of development and why Kapur believes 2026 represents the first “true renaissance of software development” since cloud became the enterprise default nearly a decade ago.
The post CloudBees CEO: Why Migration Is a Mirage Costing You Millions appeared first on The New Stack.
