OpenAI just made its boldest move yet into personal computing, acquiring Software Applications Inc., the startup behind Sky - an AI interface that can see your Mac screen and control your apps. The deal brings the team that previously sold Workflow to Apple back into the spotlight, potentially reshaping how we interact with desktop computers.
OpenAI is making its move on the desktop. The company announced Thursday it's acquired Software Applications Inc., the startup behind Sky, an unreleased AI-powered interface that can see what's on your Mac screen and take action in your apps.
The acquisition signals OpenAI's aggressive push beyond chatbots into the operating system layer, where it could directly compete with Apple's own AI ambitions. Sky represents a fundamentally different approach to AI assistance - instead of living in a separate app, it floats over your entire desktop experience, ready to help with writing, planning, coding, and more.
"We've always wanted computers to be more empowering, customizable, and intuitive," Software Applications co-founder and CEO Ari Weinstein said in a statement. "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."
The timing couldn't be more strategic. This isn't just any startup team - Weinstein and Conrad Kramer previously co-founded Workflow, which they sold to Apple where it became the automation technology now known as Shortcuts. Both worked at Apple for years before leaving in August 2023 to start Software Applications with third co-founder Kim Beverett, a former Apple senior program manager who spent nearly a decade working on Safari, WebKit, Privacy, and core Mac apps.
Now they're bringing that deep Mac expertise to OpenAI just as Apple prepares to launch an overhauled AI-powered Siri next year. Apple has already shipped Apple Intelligence features including writing helpers, live translation, and image creation across its platforms, but it's partnering with OpenAI to handle complex queries Siri can't answer.
The competitive dynamics are fascinating. Apple values privacy as core to its AI offering, marketing on-device processing and minimal data sharing. But Sky's agentic approach - watching your screen and taking actions on your behalf - raises immediate privacy questions that could concern security-minded Mac users. Recent analysis suggests , and agentic AI remains in early experimental phases.
