OpenAI Acquires Sky, an AI-Powered Interface for macOS

OpenAI has acquired Software Applications Incorporated, the company behind Sky, bringing the entire 12-person team into the organization.

The deal terms remain undisclosed, though an investment fund associated with Sam Altman held a passive investment in Software Applications Incorporated prior to the acquisition. Nick Turley, OpenAI’s vice president and head of ChatGPT, and Fidji Simo, OpenAI’s CEO of applications, personally led the negotiations.

A Screen-Aware Assistant for Mac

Sky is an AI-powered natural language interface designed specifically for macOS that floats unobtrusively over the desktop as a screen-aware assistant. The application understands what’s displayed on a Mac and takes direct actions within installed applications, though it had not yet been released to the public at the time of acquisition.

Core capabilities include helping users with writing, planning, coding, answering questions, and managing their day. The interface features built-in integrations with Calendar, Messages, Notes, Safari, Finder, Mail, and screenshot functionality, allowing it to perform tasks like creating calendar events based on conversations or finding restaurant recommendations.

Sky is customizable with custom prompts, scripts, and shortcuts that integrate natively with the application. The tool was originally scheduled to launch in summer 2025 after being unveiled in May 2025, with interested users able to sign up for a waitlist.

The Team Behind Sky

The founders of Software Applications Incorporated have notable Apple pedigree. Ari Weinstein and Conrad Kramer previously co-founded Workflow, which Apple acquired and transformed into the Shortcuts application now deeply integrated into iOS and macOS.

Kim Beverett, Sky’s co-founder and chief operating officer, spent nearly a decade at Apple as a senior program and product manager working on Safari, WebKit, Privacy, Messages, Mail, Phone, FaceTime, and SharePlay. After their contractual obligations with Apple concluded around 2023, the team left to found Software Applications Incorporated.

Embedding AI Into the Apple Ecosystem

This acquisition represents OpenAI’s commitment to embedding AI capabilities directly into the operating systems and tools people use daily, rather than limiting it to standalone applications. According to Nick Turley, “We’re building a future where ChatGPT doesn’t just respond to your prompts, it helps you get things done. Sky’s deep integration with the Mac accelerates our vision of bringing AI directly into the tools people use every day.”

OpenAI plans to integrate Sky’s capabilities and deep macOS integration into ChatGPT, bringing this functionality to hundreds of millions of users. The move arrives as OpenAI competes in an increasingly crowded space for AI-powered desktop experiences. The company recently launched ChatGPT Atlas, a web browser for macOS that embeds conversational AI directly into the browsing experience.

The acquisition comes at a time when AI companies are racing to control the interface layer between users and technology. While Apple has been developing its own AI search capabilities for Siri, it has faced setbacks with key executives departing to competitors like Meta.

For OpenAI, the Sky acquisition provides both proven talent and a technical foundation for bringing AI assistance natively to the Mac platform. Weinstein and Kramer’s experience building Workflow—which Apple valued enough to acquire and integrate system-wide—suggests they understand how to create tools that feel natural within the Apple ecosystem.

The strategic significance extends beyond macOS. OpenAI’s broader vision involves AI agents that can perform multi-step tasks across different applications and platforms. Sky’s screen-aware capabilities and app control represent building blocks for that future, where AI doesn’t just generate text but actively assists with complex workflows.

With Sky’s team now inside OpenAI, the company gains expertise in building lightweight, performant interfaces that sit between users and their operating systems. That knowledge will prove valuable as OpenAI continues developing tools like AgentKit, its platform for designing and deploying AI agents.

The deal also positions OpenAI to compete more directly with Microsoft, its largest investor, which has integrated Copilot across its own productivity suite. By building native Mac capabilities, OpenAI can reach users across the Apple ecosystem without relying solely on web interfaces or third-party integrations.

For Mac users, the acquisition suggests that ChatGPT’s capabilities will soon extend beyond a browser tab or standalone app into a system-level assistant that understands context across applications. Whether that takes the form of Sky’s original floating interface or a deeper integration into ChatGPT’s existing desktop app remains to be seen.

OpenAI has not announced a timeline for when Sky’s technology will appear in ChatGPT or other OpenAI products, though Turley’s comments indicate integration work is already underway. With the team now in-house and the technology proven, the pieces are in place for OpenAI to bring screen-aware assistance to its hundreds of millions of users in the months ahead.