OpenAI acquired the startup behind Sky. But there’s more than what meets the eye.
OpenAI just made a move that tech decision-makers need to pay more attention to.
The company acquired Software Applications Incorporated, the startup behind Sky, a Mac-native AI interface that can see your screen and take action in your apps.
But there’s a plot twist.
The founders, Ari Weinstein and Conrad Kramer, previously built “Workflow,” the iOS automation app that Apple bought in 2017. And then transformed into Shortcuts.
These aren’t random engineers OpenAI picked up. These are the people who taught millions of iPhone users that automation doesn’t have to be arcane. They made it intuitive. And now they’re bringing that philosophy to desktop AI at OpenAI, not Apple.
Sky isn’t just another chatbot.
Sky is a natural language interface that floats over your desktop.
It watches what you’re doing- writing, coding, planning. And can take action using the apps you already have open. It’s not a chatbot in a window. It’s ambient AI that lives in your workflow.
It’s fundamentally different from typing prompts into ChatGPT.
Sky understands screen content and can interact with your installed applications, i.e., it bridges the gap between “AI that talks” and “AI that does.”
And OpenAI’s betting that this is where the puck is going. Nick Turley, VP and Head of ChatGPT at OpenAI, put it plainly: “We’re building a future where ChatGPT doesn’t just respond to your prompts, it helps you get things done.”
But the timing isn’t coincidental.
This acquisition landed just two days after OpenAI launched ChatGPT Atlas, its AI-powered browser for Mac. Atlas handles web tasks. Sky handles OS-level tasks. Together, they form OpenAI’s play to own the entire computing interface on Apple’s platform.
That’s not a product strategy. That’s infrastructure.
But here’s where it gets interesting for decision-makers: Sky never officially launched. OpenAI bought it before it reached the market. The startup had raised $6.5 million from investors including Sam Altman, Figma CEO Dylan Field, Context Ventures, and Stellation Capital. All twelve employees are joining OpenAI.
It isn’t an acqui-hire where the product gets shelved. OpenAI made that clear: they plan to integrate Sky’s deep macOS capabilities into ChatGPT.
There’s a question that no one’s asking.
Do people actually want an AI layer floating over their desktop?
The promise sounds great: context-aware assistance that adapts to your intent. But the execution is brutally complex. Deep OS integration means permission management, security reviews, and all the messy coordination that turns sleek demos into bloatware.
If OpenAI can pull off native desktop integration without turning ChatGPT into bloatware, they’ll have something. If they can’t, this becomes another case where the product vision dies during integration.
Whether you’re evaluating AI tools for your team or just watching where the industry’s headed, this acquisition isn’t background noise. It’s a signal.
OpenAI isn’t just building better language models. They’re building the interface layer that will determine how we interact with computers for the next decade.
And they just hired the people who’ve done it before.
