Mainframe modernization is one of the most expensive and dangerous undertakings in enterprise IT. Critical systems written in COBOL or PL/1 often run mission-critical workloads for banks, insurers, airlines, and governments, but the original authors are long gone, documentation is sparse, and a single behavioral regression can cause outages or financial loss. Mechanical Orchard was founded in 2022 in San Francisco by Rob Mee, the founder and former CEO of Pivotal Labs and Pivotal Software, along with co-founders from the Pivotal world, to make this migration safe and tractable using AI.
The company's platform, Imogen, takes an observation-first approach. Rather than trying to read and translate impenetrable legacy code directly, Imogen instruments the running system and captures real data flows across component interfaces, building a behavioral specification of what the software actually does in production. That specification then guides AI-assisted code generation to produce a modern, cloud-native equivalent, and crucially, it lets the platform continuously prove equivalence between old and new systems at every step of the migration.
This equivalence-proving methodology is the heart of Mechanical Orchard's pitch: enterprises can move off the mainframe incrementally and with confidence, validating that the new system behaves identically before cutting over. It transforms a multi-year, high-risk big-bang rewrite into a measurable, de-risked process.
Mechanical Orchard has attracted strong investor backing. After a $7 million seed round, it raised a $24 million Series A led by Emergence Capital in early 2024 at a roughly $95 million valuation, with participation from Industry Ventures, Spider Capital, Bloomberg Beta, Cendana Capital, and Webb Investment Network. It later raised a $50 million Series B led by GV (Google Ventures). With the enterprise mainframe modernization market valued in the tens of billions and growing, Mechanical Orchard is positioned to help the largest, most regulated organizations finally escape legacy lock-in.