OpenAI Acquires AI Automation Startup Sky

OpenAI announced today its acquisition of Software Applications, Inc., the developer behind the upcoming macOS automation tool Sky. The deal brings onboard a team with deep roots in Apple's ecosystem, including co-founders Ari Weinstein and Conrad Kramer—the original creators of Workflow, which Apple acquired and rebranded as Shortcuts.

About Sky: AI-Powered macOS Automation

Sky is an unreleased personal assistant designed to observe user activity (such as writing or coding) and automatically perform context-aware actions across applications. Its standout feature is natural language processing, enabling it to interpret on-screen content and execute tasks seamlessly.

The Apple Connection

The founding team boasts extensive Apple experience:

• Ari Weinstein & Conrad Kramer: Developed Workflow (acquired by Apple in 2017), now core to iOS/macOS Shortcuts.
• Kim Beverett: Former Apple engineer with contributions to Safari, WebKit, and privacy projects.

Strategic Alignment with OpenAI

In a statement, OpenAI emphasized Sky’s potential to advance context-aware AI interfaces:

"Progress in AI isn’t just about intelligence—it’s about adapting to user intent and enabling seamless collaboration."

The acquisition will integrate Sky’s macOS integration expertise into ChatGPT, though specifics on product integration remain undisclosed.

Funding and Deal Terms

While financial details were not revealed:

• Sky previously raised $6.5 million from investors including OpenAI CEO Sam Altman and Figma CEO Dylan Field (per PitchBook data).
• All Sky team members will join OpenAI post-acquisition.

Key Points:

• 🚀 Acquisition: OpenAI buys Sky, an AI automation tool from Apple Shortcuts’ original team.
• 💡 Technology: Sky uses NLP to automate tasks by interpreting screen content.
• 🔍 Strategic Fit: Enhances ChatGPT’s macOS integration and contextual awareness.
• 💰 Funding: Sky had $6.5M in backing pre-acquisition.