Deeper AI Integration for macOS: Creators of Apple's Shortcuts Move to OpenAI
Air Weinstein and Conrad Kramer founded Workflow, which Apple then bought. Afterward, they built an AI app for Mac. The company is now landing at OpenAI.
Sky in action: Never released (pixelated graphic generated by manufacturer).
(Image: Software Applications Incorporated)
Developers of a very Apple-centric product will now be working at OpenAI: The company Software Applications Incorporated will become part of the ChatGPT parent company. The company announced this on its website. The creators Ari Weinstein and Conrad Kramer, known from the Shortcuts app alias Kurzbefehle, are moving to OpenAI with their app Sky. It is expected that ChatGPT could be integrated much more deeply into macOS in the future than is the case currently through the official app.
Free, Apple, Free Again – Now OpenAI
Weinstein and Kramer initially developed the popular automation solution Workflow themselves. Apple found this so interesting that the company bought it outright in 2017, redesigned it, and then integrated it as the Shortcuts app into its systems – macOS, iOS, iPadOS, and partially watchOS. Kramer and Weinstein then also stayed with Apple for a while: Kramer left in 2019, Weinstein in 2023. The two then founded Software Applications Incorporated, which then focused on developing an AI automation solution called Sky.
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Sky was first presented to the public in the summer of 2025, but only as a website with demo videos. OpenAI seems to have been so impressed by this – including the still private code – that the AI company decided to acquire it. Sky combined elements of Shortcuts with chatbot control. For example, it was intended to allow access to the address book, the messages app, and many other Mac elements to automate them. With natural language, one could, for instance, request to retrieve a calendar entry from emails or perform actions with open windows – apparently with any app on the computer. This is reminiscent of the context-sensitive Siri on the iPhone, which Apple will likely release in the spring.
Targeting "Hundreds of Millions" of Users
It is still unclear what OpenAI specifically plans to do with Sky – possibly the app will be released as planned, just directly from OpenAI. In a statement, Weinstein, CEO of Software Applications Incorporated, said his team had always wanted computers to become more powerful, adaptable, and intuitive. "With LLMs, we can finally put these puzzle pieces together." That's why they developed Sky. The app "flows" over the desktop "to help you think and create." With the acquisition by OpenAI, he now hopes to "bring [our vision] to hundreds of millions of people."
The purchase price was not initially disclosed. In addition to Weinstein and Kramer, other employees will also move to OpenAI – including other individuals who once worked at Apple. OpenAI recently introduced its first own browser with Atlas, which will initially only be available on macOS.
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