In a bold and strategic move, OpenAI has acquired Software Applications, the startup behind Sky, an AI-powered desktop interface built specifically for macOS. The deal signals OpenAI’s next major leap — moving from a conversational AI platform to a deeply integrated computing companion capable of transforming how millions of users interact with their computers.
🌌 Sky: The Floating AI Companion
Sky, designed to “float” above your desktop, acts as a seamless AI layer that enhances creativity, productivity, and user control. Instead of being confined to a chat window, Sky sits across the user interface, allowing natural conversations to drive real actions — like editing files, managing tasks, writing code, summarizing emails, or generating visual assets — all without breaking your workflow.
“We’ve always wanted computers to be more empowering, customizable, and intuitive,”
said Ari Weinstein, co-founder and CEO of Software Applications.
“With large language models, 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.”
Sky represents a new class of “agentic” AI systems — not just reactive assistants, but autonomous digital partners capable of performing multi-step operations, adapting to context, and learning from user intent over time.
🍏 An Apple Legacy: The Team Behind Workflow and Shortcuts
The Sky founding team brings a distinguished pedigree from Apple’s ecosystem.
- Ari Weinstein and Conrad Kramer previously co-founded Workflow, an automation tool Apple acquired in 2017. Workflow’s technology evolved into Apple Shortcuts, a cornerstone of iOS and macOS productivity.
- Kim Beverett, Sky’s third co-founder and COO, spent nearly a decade at Apple leading projects across Safari, WebKit, Messages, Mail, FaceTime, and SharePlay.
Their track record is proof of concept — they’ve already shaped how billions of users interact with Apple devices. Now, with OpenAI’s resources, they aim to redefine desktop computing through an AI-first interface.
💬 A Perfect Fit for OpenAI’s Expanding Ecosystem
The acquisition was led by Nick Turley, Head of ChatGPT, and Fidji Simo, OpenAI’s CEO of Applications (formerly of Instacart and Meta). OpenAI’s board unanimously approved the deal. While financial terms remain undisclosed, data from PitchBook indicates Software Applications had raised $6.5 million in seed funding from notable investors, including OpenAI CEO Sam Altman, Figma CEO Dylan Field, Context Ventures, and Stellation Capital.
The acquisition follows OpenAI’s continued push into consumer-grade interfaces, including:
- ChatGPT desktop apps for macOS and Windows
- AI voice assistants powered by real-time reasoning
- And a growing integration with Microsoft’s Windows ecosystem through Copilot
Sky now represents the company’s most direct step toward embedding its technology natively into the Apple environment, an ecosystem previously resistant to outside AI tools.
🧩 Apple’s Catch-Up Race in AI
Apple, often cautious with emerging technologies, has begun integrating AI under its new framework called Apple Intelligence — which powers writing tools, image generation, visual search, and Siri enhancements. However, Apple’s approach prioritizes privacy and local computation, often at the cost of speed and adaptability.
An agent like Sky — capable of viewing, interpreting, and interacting with your screen — could raise privacy questions among Apple’s user base. Apple’s AI strategy is focused on protecting on-device data, while OpenAI’s model relies on cloud-based intelligence and continuous learning.
That difference highlights a deeper philosophical divide:
- Apple’s AI = Private, local, incremental
- OpenAI’s AI = Connected, cloud-driven, and ambitious
If Sky becomes deeply integrated into macOS — even unofficially — it could set a new benchmark for AI-native computing, forcing Apple to accelerate its Siri overhaul scheduled for 2026.
🔍 A New Era of Agentic AI
Sky’s acquisition fits perfectly into the industry’s shift toward agentic AI — intelligent systems that don’t just respond, but act. These agents can plan tasks, operate apps, and automate workflows independently. Tech giants like Anthropic, Google DeepMind, and Microsoft are all racing toward the same goal: the creation of “AI co-pilots” that become essential to daily work.
Sky’s interface — already capable of generating code, manipulating files, and creating visual prototypes — could soon evolve into a Mac-native agent integrated with ChatGPT’s reasoning engine and OpenAI’s new API ecosystem.
📈 Strategic Implications
The timing of this acquisition is no coincidence. OpenAI is positioning itself not just as a model provider, but as a platform company capable of powering every layer of digital experience — from chat to OS-level control.
With Sky, OpenAI could soon offer:
- A ChatGPT-powered desktop environment rivaling Apple’s Siri and Microsoft Copilot
- Deeper integration across creative tools like Figma, Adobe, and Xcode
- And potential enterprise-grade workflows for developers and designers
This could also pave the way for OpenAI’s own operating environment — a lightweight, AI-augmented shell over macOS and Windows that redefines how we “use” computers altogether.
💼 Deal Details and Outlook
While specific financial terms haven’t been disclosed, Sky’s investor list offers clues about its valuation and potential synergy:
- Sam Altman’s personal fund held a passive interest
- Figma’s Dylan Field brings design ecosystem expertise
- Context Ventures and Stellation Capital backed early development
The deal, approved by OpenAI’s board, was described internally as a “strategic acquisition to accelerate next-gen AI applications.”
🚀 The Bigger Picture
Sky’s arrival at OpenAI comes at a time when AI assistants are shifting from novelty to necessity. As enterprises, developers, and creatives demand smarter tools that blend reasoning with action, OpenAI is laying the groundwork for an AI-first computing era — one where your desktop becomes as conversational and intelligent as ChatGPT itself.
If successful, Sky could be the foundation of a future OpenAI-powered Mac layer, capable of transforming everyday computing into an intelligent, collaborative experience — one that’s always ready to help you think, create, and act.