A growing wave of corporate technology chiefs is mapping exit strategies from major enterprise software systems including VMware, SAP's ERP suites, and Oracle's Java, driven by rising licensing fees, vendor support deadlines, and the emerging capabilities of AI-assisted coding. About 22% of IT leaders are actively reconsidering core enterprise systems such as ERP and CRM, according to research from IT analyst firm Gartner cited in the report. Meanwhile, more than nine in 10 IT leaders expect disruption in the software market, with many reassessing niche and point software solutions, especially low-complexity edge applications.

The pressure to switch is most acute for VMware customers, where a recent survey by third-party support vendor Rimini Street found 90% of IT leaders at VMware customers looking for alternatives following significant price increases by Broadcom after its acquisition of the virtualization market leader nearly three years ago. SAP has announced the end of support for its popular, perpetually licensed ECC ERP package in 2027, pushing customers toward its subscription-based S/4HANA suite with an ever-shifting end-of-customer-support deadline that has prompted customer backlash. Oracle switched Java to per-employee pricing in 2023, meaning subscribers now pay for staff who've never opened a Java app. In a survey released in February by cloud management software vendor CloudBolt, 86% of IT decision-makers at large North American companies said they were shrinking their VMware use, yet just 2% of respondents had shifted three-quarters of their environments away from the virtualization giant.

Patrick Connaughton, chief of research at Gartner, notes that IT leaders aren't planning wholesale replacements of core systems yet, but that's likely to change in coming years as AI agents replace expensive user interfaces and seat-based pricing while AI-enabled coding prompts leaders to rethink whether they need to buy enterprise software. "Most IT leaders expect their current software models to be upended as customer fatigue with vendor lock-in, bloated suites, and diminishing returns drives a shift away from point solutions," Connaughton states. "A fundamental buy-versus-build inversion is under way as rapid adoption of agentic coding tools enables organizations to build custom alternatives faster and at lower cost." John Burns, senior director of finance systems and transformation at equipment rental firm Herc Rentals, identifies ERP as a huge target for replacement, with finance departments often paying twice—once in license fees and again in workarounds.

The path to escape remains treacherous, however, with incumbent vendors holding advantages through institutional trust, regulatory moats, and data lock-in that will keep most CIOs from making major replacements in the next three to six years, according to the report. Detangling from a software suite like VMware can take up to four years, with companies needing to map data, redesign controls, and retain staff while running two systems side by side. Kevin M. Coles, founder of factional CIO and CTO firm Coles Technical Group, observes that customers stay even when they say they'll leave because the license is rarely the real cost of switching—the real costs are the integrations nobody documented, the reports finance depends on, the staff who only know one console, and the year of running two systems simultaneously. Brad LaPorte, strategic advisor at IT advisory firm Lionfish Tech Advisors, compares the challenge to moving between houses: "VMware is the house you've lived in for 15 years, with wiring from half your business running through the walls, and getting out means opening every one of those walls while keeping the lights on." The report recommends IT leaders inventory all use cases, map every workload and integration, and price the exit only after understanding the full scope, because most exit estimates cover the license and miss the wiring entirely. The most useful step a CIO can take is running that exercise now, before the renewal notice arrives—even if they stay, a credible exit plan is the best leverage they'll ever have in negotiation. Enterprises comfortable with vendor concentration may find themselves trading known dependencies for new ones, while those prioritizing agility will need to accept years of parallel infrastructure and divided attention during any transition.