OpenAI acquires AI startup by ex-Apple engineers behind Workflow, Shortcuts

OpenAI acquires Software Applications Inc., the startup behind Sky, an AI interface for macOS built by ex-Apple engineers behind Workflow and Shortcuts

OpenAI has announced the acquisition of Software Applications Incorporated, the company behind Sky, an AI-powered natural language interface for Apple Macs. In a press note, OpenAI stated that with this move, it plans to bring “Sky’s deep macOS integration and product craft into ChatGPT,” and that all members of the Sky team will join OpenAI.

Sky: The AI interface for macOS

For the uninitiated, Sky is an unreleased AI interface designed to understand what’s on a user’s screen and perform contextual tasks such as writing, planning, and coding directly within active windows.

 

Software Applications Incorporated previewed the interface earlier this year, showcasing its ability to interact with macOS at a system level.

Founded in 2023 by the team behind the Workflow app, which Apple acquired and transformed into Shortcuts, Sky’s design philosophy focuses on natural interaction and automation.

Deeper macOS integration for ChatGPT

OpenAI said it will bring Sky’s macOS integration and product expertise into ChatGPT’s ecosystem.

 

“We’re building a future where ChatGPT doesn’t just respond to your prompts — it helps you get things done,” said Nick Turley, VP and Head of ChatGPT. “Sky’s deep integration with the Mac accelerates our vision of bringing AI directly into the tools people use every day.”

 

Software Applications Incorporated co-founder and CEO Ari Weinstein added that the team’s goal was to make computers “more empowering, customisable, and intuitive.”

 

“With LLMs, 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,” Weinstein said. “We’re thrilled to join OpenAI to bring that vision to hundreds of millions of people.”

Former Apple engineers behind Sky

As reported by TechCrunch, Software Applications Incorporated was co-founded in 2023 by Ari Weinstein and Conrad Kramer, along with Kim Beverett, a former senior Apple product manager who worked on Safari, Messages, FaceTime, and SharePlay.

 

Weinstein and Kramer previously sold their Workflow app to Apple in 2017, which later became the foundation for Shortcuts, Apple’s built-in automation system across iOS, iPadOS, and macOS.

 

Although Sky was never publicly released, early reports suggested it functioned as a Mac-native AI assistant capable of performing system-level actions through natural language.

 

The acquisition gives OpenAI direct access to a team with deep macOS engineering and UX design experience, bolstering ChatGPT’s desktop ambitions.

OpenAI’s broader desktop ambitions

The Sky acquisition comes shortly after OpenAI unveiled ChatGPT Atlas, its new AI-powered web browser that integrates ChatGPT directly into browsing workflows.

With Atlas handling web tasks and Sky extending AI to desktop workflows, OpenAI appears to be positioning ChatGPT as a multi-environment assistant capable of managing everything from research and writing to system-level actions.

 

The company said it will share more details as it integrates Sky’s technology into ChatGPT in the coming months, potentially shaping the next generation of AI-powered macOS experiences.