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OpenAI buys the team behind Sky, an unreleased AI interface for Mac

Sky acts as an on-screen assistant that can view content and take actions across apps in real time. The product was built by the creators of Workflow, the automation app Apple rebranded as Shortcuts.

byKerem Gülen
October 24, 2025
in Industry
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OpenAI announced its acquisition of Software Applications, Inc., the company behind the AI-powered Mac interface Sky. The move aims to embed OpenAI’s technology into daily consumer and business operations on Apple computers through the unreleased software.

The acquired product, Sky, had not been released publicly. It is engineered as an AI-powered natural language interface designed to function alongside users during their daily computer activities, including writing, planning, and coding. The system is able to see on-screen content and execute actions within applications on the user’s behalf, a functionality similar to that of emerging AI browsers. The acquisition represents a step toward integrating OpenAI’s technology directly into the workflow of individuals and businesses operating within the Mac ecosystem.

Ari Weinstein, co-founder and CEO of Software Applications, provided a statement regarding the acquisition. “We’ve always wanted computers to be more empowering, customizable, and intuitive. With LLMs, we can finally put the pieces together. That’s why we built Sky, an AI experience that floats over your desktop to help you think and create. We’re thrilled to join OpenAI to bring that vision to hundreds of millions of people,” Weinstein said.

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The leadership team at Software Applications has a history of successful ventures involving Apple. Weinstein and fellow co-founder Conrad Kramer previously established Workflow, a company they sold to Apple, where its technology was integrated and rebranded as the Shortcuts feature. Both founders worked at Apple for several years following that acquisition before departing to create Software Applications in August 2023. The third co-founder and COO, Kim Beverett, is also an Apple veteran, having spent nearly a decade as a senior program and product manager working on technologies including Safari, WebKit, Privacy, Messages, Mail, Phone, FaceTime, and SharePlay.

The acquisition occurs as Apple prepares its own artificial intelligence initiatives. The company is expected to launch a redesigned Siri with enhanced AI capabilities next year. Apple has already deployed features under its “Apple Intelligence” brand, which include writing aids, live translation, image generation, and visual search across its platforms, including the Mac. The company is also collaborating with OpenAI to direct Siri queries that the assistant cannot answer to the ChatGPT service.

Apple provides developers with a Foundation Models framework, enabling the integration of local AI models directly into applications. The company presents privacy as a central component of its AI strategy. An agentic system like Sky, which has the capability to view a user’s screen and perform actions autonomously, could introduce security concerns for some customers. The field of agentic AI is still nascent, and recent reviews of AI browsers have highlighted existing safety risks. These factors may contribute to a longer development timeline for Apple to release a Mac AI system with capabilities comparable to Sky’s.

The financial terms of the acquisition were not made public. According to data from Pitchbook, Software Applications had previously secured $6.5 million in funding from a group of investors that included OpenAI CEO Sam Altman, Figma CEO Dylan Field, Context Ventures, and Stellation Capital. OpenAI specified that Altman’s involvement was a passive interest held through an investment fund. The acquisition was managed by Nick Turley, Head of ChatGPT, and Fidji Simo, OpenAI’s CEO of Applications, and received approval from OpenAI’s board of directors.


Featured image credit

Tags: openAIsky

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