OpenAI has acquired Software Applications Incorporated, the company whose core team developed Apple's Shortcuts app. The deal brings expertise in AI-driven macOS interfaces to enhance ChatGPT. Financial terms remain undisclosed.
OpenAI announced the acquisition of Software Applications Incorporated (SAI) on October 23, 2025, signaling deeper integration into operating systems. SAI's team, previously instrumental in creating Shortcuts for Apple platforms, had been developing Sky—a context-aware AI layer for macOS that uses Apple APIs and accessibility features to feed screen context to large language models. This allows the AI to execute plain-language commands across multiple applications, generating workflows on the fly without setup.
The SAI co-founders—Ari Weinstein (CEO), Conrad Kramer (CTO), and Kim Beverett (Product Lead)—will join OpenAI. They had worked together at Apple after the company acquired their prior venture, which produced the Workflows automation tool integrated into Shortcuts. The trio left Apple to focus on Sky, aiming for seamless AI control of macOS environments.
“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 representative stated in the company's blog post. OpenAI plans to “bring Sky’s deep macOS integration and product craft into ChatGPT,” expanding beyond question-and-answer functionalities.
This move echoes the recent launch of Atlas, OpenAI's ChatGPT-driven web browser. It leverages the team's macOS knowledge to enable ChatGPT to act directly within users' environments. OpenAI's desktop efforts have focused on macOS, targeting developers who favor the platform. While it's unclear if Sky will evolve as originally envisioned, both companies emphasize ambitions for broader AI applications.