The stealth-built desktop assistant brings OpenAI one step closer to embedding agentic AI into everyday computing — and right into Apple’s backyard
OpenAI Buys Sky to Power Mac-Based AI Assistants
OpenAI has acquired Software Applications, Inc., the company behind Sky, a natural language AI interface for Mac designed to work seamlessly alongside users as they write, plan, code, and use their favorite apps.
- Sky was never publicly released, but early previews show it functions like a floating AI assistant, able to see your screen and take actions across apps — a step toward agentic AI.
- The move reflects OpenAI’s goal to make its LLMs (large language models) an integrated part of everyday computing, particularly within creative and productivity workflows on macOS.
“With LLMs, we can finally put the pieces together,” said co-founder Ari Weinstein. “We’re thrilled to join OpenAI to bring that vision to hundreds of millions of people.”
A Team with Apple DNA — and a Proven Exit
Sky’s founding team includes high-profile Apple alums:
- Ari Weinstein and Conrad Kramer, co-founders of Workflow, which Apple acquired in 2017 and transformed into Shortcuts.
- Kim Beverett, a former senior Apple program and product manager who worked across key apps and services including Safari, Messages, FaceTime, and SharePlay.
Their collective experience in deep Apple platform integration makes the acquisition especially valuable as OpenAI looks to build consumer-facing, system-level agents.
Why Sky Matters for OpenAI’s Consumer Strategy
Sky represents a new class of context-aware, on-device AI assistants—similar in function to AI browsers or copilots, but embedded directly into the desktop environment.
- It’s capable of interpreting screen content, understanding user workflows, and performing real tasks on the user’s behalf.
- It’s designed for creators, students, developers, and professionals—people whose daily work could be streamlined with continuous AI assistance.
Sky’s design hints at OpenAI’s intent to go beyond chatbots and build agentic AI interfaces that are deeply integrated with a user’s computing environment.
Apple’s AI Push and a Potential Competitive Rift
Apple has been slower to roll out full AI agents, instead focusing on privacy-first AI with Apple Intelligence, which powers writing assistance, image generation, translation, and visual search.
- Apple is reportedly working on an overhauled Siri, with ChatGPT integration for complex queries.
- However, Apple’s privacy stance may limit how quickly it embraces agentic AI — the kind that observes and acts across apps like Sky does.
This leaves a potential gap that OpenAI could exploit, especially on macOS, where Apple’s own AI agents may lag behind in functionality due to security constraints.
Deal Details: Strategic and Investor-Aligned
Terms of the deal were not disclosed, but Sky had previously raised $6.5 million from:
- OpenAI CEO Sam Altman (via a fund, disclosed as a passive interest)
- Figma CEO Dylan Field
- Context Ventures, Stellation Capital, and others
The acquisition was led by Nick Turley, Head of ChatGPT, and Fidji Simo, OpenAI’s CEO of Applications, and approved by OpenAI’s board.
With the acquisition, Sky’s team will likely contribute directly to ChatGPT’s desktop experience and possibly to future native OpenAI apps on Mac.
The Bigger Picture: Toward a Personalized AI Operating System
Sky’s vision aligns with a broader industry movement toward agentic AI — systems that don’t just answer questions but can observe, reason, and act.
- Tools like OpenAI’s ChatGPT with memory, Atlas browser, and now Sky, reflect OpenAI’s shift from passive assistant to proactive AI co-worker.
- With Sky, OpenAI gains both technology and talent that could help it leapfrog traditional platform limitations and build the AI OS layer of the future.
