OpenAI has acquired Software Applications Incorporated, the company founded by former Apple engineers who created Workflow and later Apple Shortcuts. The move signals a major step toward bringing ChatGPT deeper into macOS, transforming it from a conversational assistant into an intelligent system that can understand context and take real action across the desktop.
Software Applications was co-founded by Ari Weinstein and Conrad Kramer, both well-known in Apple’s automation community. The pair originally developed Workflow, an iOS automation app that Apple purchased in 2017 and turned into Shortcuts, which has since become a central feature across iPhone, iPad, and Mac. Weinstein left Apple in 2023 and Kramer in 2019, and the two reunited to launch a new venture, creating a Mac-native AI assistant called Sky.
Sky never officially launched but drew attention for its combination of natural language and visual context. It could identify what was open on a user’s screen, answer questions, and perform actions directly inside Mac apps. OpenAI has now confirmed that it will integrate Sky’s deep macOS capabilities into ChatGPT, with Weinstein, Kramer, and the entire Sky team joining to lead development.
In a statement, Weinstein said that the team always wanted computers to be more empowering, customizable, and intuitive. “With LLMs, we can finally put the pieces together,” he explained. “That is why we built Sky, an AI experience that floats over your desktop to help you think and create. We are thrilled to join OpenAI to bring that vision to hundreds of millions of people.”
The acquisition highlights how OpenAI envisions ChatGPT’s future. Instead of remaining a text-only chatbot, it will evolve into a true on-screen collaborator capable of understanding context and executing commands across the Mac ecosystem. Sky’s technology provides the missing link between conversational AI and system-level functionality.
This announcement also follows the recent release of ChatGPT Atlas, OpenAI’s new Mac browser that directly integrates ChatGPT into the web experience. Atlas allows users to browse, summarize, and automate actions within webpages.
Software Applications previously raised 6.5 million dollars from investors, including OpenAI CEO Sam Altman and Figma CEO Dylan Field. The acquisition was approved by OpenAI’s independent board, although financial terms were not disclosed.
