OpenAI has just announced their acquisition of Software Applications Incorporated. They are the startup behind Sky, an AI powered natural language interface designed for Mac computers. Sky was built to seamlessly integrate with native Mac applications by viewing screen content and performing actions in real-time to assist users throughout their day.
The deal signals OpenAI’s push to embed ChatGPT directly into tools millions already use, bridging Mac’s desktop experience with the power of large language models.
“We’ve always wanted computers to be more empowering, customizable, 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. We’re thrilled to join OpenAI to bring that vision to hundreds of millions of people,” Software Applications co-founder and CEO Ari Weinstein said in a statement.
Users can use Sky to summarize documents, compose emails, manage calendar entries, and execute multi-step tasks across a variety of apps without prior setup. This ambient AI experience moves beyond static text responses, extending AI capabilities into context-aware, real-time productivity assistance.
The team behind Sky brings significant expertise and a proven track record, especially with automation. Ari Weinstein and Conrad Kramer co-founded Workflow, an iOS automation app acquired by Apple in 2017, later evolving into Apple’s Shortcuts feature.
Their experience in delivering accessible and powerful automation tools for Apple platforms forms the base for Sky’s macOS integration. Kim Beverett, Sky’s co-founder and COO, also boasts a decade of experience at Apple working on key technologies like Safari, WebKit, and Messages.
Strategic Importance
This acquisition aligns with OpenAI’s vision for ChatGPT to not merely be a conversational engine but a productivity partner that “helps you get things done.”
“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,” said Nick Turley, VP & Head of ChatGPT.
The timing also follows OpenAI’s launch of ChatGPT Atlas, a new AI-powered web browser that leverages ChatGPT’s agent mode to automate complex tasks online. Sky extends this multi-platform AI support beyond the browser to the core operating system level, enabling richer interactions on Mac devices.
Given Sky’s agentic AI capability to view and interact with users’ screens and applications, privacy and security are major concerns. While Apple has advanced AI features across its ecosystem under the “Apple Intelligence” brand, integrating an always-on AI assistant with screen access still presents various challenges.
Experts note that agentic AI systems demand stringent safety measures to prevent data leaks, unauthorized access, or malicious prompt injections. OpenAI and Apple will need to navigate these carefully to deliver a trusted user experience.
Though the exact financial terms were not disclosed, OpenAI CEO Sam Altman previously held a passive investment stake in Software Applications Inc through an investment fund. Prior to acquisition, Sky raised $6.5 million from notable backers including Altman, Figma CEO Dylan Field, Context Ventures, and Stellation Capital. The acquisition was led by Nick Turley and Fidji Simo and approved by OpenAI’s independent Transaction and Audit Committees.
OpenAI’s purchase of Sky follows aggressive acquisition activity in 2025, including a $1.1 billion acquisition of product development firm Statsig and over $6 billion acquisition of AI hardware startup io, led by former Apple designer Jony Ive. Industry competitors like Anthropic, Microsoft, and Google are also rapidly advancing desktop and search AI integrations.
Unlike existing chatbots confined to browsers or standalone apps, Sky’s approach prioritizes ambient contextual assistance directly within macOS workflows.
“Incredible potential for a new class of assistive AI,” said Federico Viticci, MacStories.
