With new acquisition, OpenAI signals plans to integrate deeper into the OS

OpenAI has acquired Software Applications Incorporated (SAI), perhaps best known for the core team that produced what became Shortcuts on Apple platforms. More recently, the team has been working on Sky, a context-aware AI interface layer on top of macOS. The financial terms of the acquisition have not been publicly disclosed.

“AI progress isn’t only about advancing intelligence—it’s about unlocking it through interfaces that understand context, adapt to your intent, and work seamlessly,” an OpenAI rep wrote in the company’s blog post about the acquisition. The post goes on to specify that OpenAI plans to “bring Sky’s deep macOS integration and product craft into ChatGPT, and all members of the team will join OpenAI.”

That includes SAI co-founders Ari Weinstein (CEO), Conrad Kramer (CTO), and Kim Beverett (Product Lead)—all of whom worked together for several years at Apple after Apple acquired Weinstein and Kramer’s previous company, which produced an automation tool called Workflows, to integrate Shortcuts across Apple’s software platforms.

The three SAI founders left Apple to work on Sky, which leverages Apple APIs and accessibility features to provide context about what’s on screen to a large language model; the LLM takes plain language user commands and executes them across multiple applications. At its best, the tool aimed to be a bit like Shortcuts, but with no setup, generating workflows on the fly based on user prompts.