OpenAI Bought a Startup Founded by Apple Shortcuts Developers

AuthorJeff Cochin

Everyone probably got used to OpenAI dropping new versions of ChatGPT now and then. It’s already reached version 5, and you could argue endlessly about which one feels smarter or faster, still, OpenAI (the company behind ChatGPT) continues to lead the AI development. And yesterday, October 23, they threw in a surprise: an announcement that they had acquired Software Applications Incorporated.

At first glance, it may not seem relevant to Apple fans, but that startup was founded by the very same developers who created Apple’s Shortcuts app and were working on a new AI assistant for Mac, called Sky. So, naturally, our ears perked up. Apple DNA meets OpenAI’s model magic? That sounds worth attention. Let’s look at what Sky actually is, and how this acquisition could affect Apple’s own vision for intelligent tools on the Mac.

Who Are the People Behind Sky?

Before we get to the main point, it’s fair to introduce the people behind Software Applications Incorporated (the very startup OpenAI just added to its collection). Once you see who stands behind it, the rest of this story will make much more sense, and you’ll understand why Sky keeps popping up in this story.

The team behind Sky includes Ari Weinstein and Conrad Kramer, the duo who created Workflow, the automation app Apple bought in 2017 and later turned into Shortcuts. After finishing their chapter at Apple, Kramer in 2019 and Weinstein in 2023, they teamed up with Kim Beverett, a former Apple product manager who spent years shaping Safari and Messages. Together, they founded Software Applications Incorporated in 2023, quickly raising about $6.5 million with Sam Altman (OpenAI’s CEO) listed among early backers.

If you’ve never really used Shortcuts, give it a try. It’s one of the most underrated features on any Apple device. Our team constantly relies on it, for example, to clean up duplicate photos, create quick notes, or set up simple automation chains for daily routines.

Armed with years of Apple experience, the trio built their next creation – Sky, an AI assistant for Mac. This AI assistant that sits above your Mac desktop and actually gets things done. It understands what you’re working on, interacts with your apps, and completes tasks, like summarizing a webpage, turning it into a calendar event, and messaging your team, all through simple commands.

Before OpenAI stepped in, it was still in limited testing, but early testers described it as an assistant that feels like the missing piece of macOS. Or, as Ari Weinstein put it, “an AI experience that floats over your desktop to help you think and create.” In other words, the kind of feature Apple fans would expect from Apple, if OpenAI hadn’t done it first.

What OpenAI Plans to Do with Sky?

When OpenAI bought Software Applications Incorporated, it got a team that knows how to make Apple’s software feel effortless. The company said it would “bring Sky’s deep macOS integration into ChatGPT,” meaning ChatGPT could soon live on your desktop, access your apps, and help with real tasks instead of just chatting.

The Sky team (Ari Weinstein, Conrad Kramer, and Kim Beverett) joined OpenAI to make this vision real. Their automation expertise fits perfectly with OpenAI’s goal to turn ChatGPT into an assistant that works across macOS. In practice, you could ask it to schedule a meeting or summarize a document, and it would quietly handle it inside your apps. OpenAI CEO Sam Altman, an early investor in Sky, clearly saw the potential. With the team on board, OpenAI can now plug its top-tier models directly into a Mac-native environment. The company recently launched ChatGPT Atlas, a browser for Mac with built-in automation.

With Sky’s technology, that same logic could extend to Mail, Calendar, or Finder, basically, anywhere you click. And since OpenAI also collaborates with Jony Ive on AI hardware, it’s clear they’re building something bigger.

What This Means for Mac Users and Apple’s Ecosystem

For Mac users, OpenAI’s acquisition of the Sky team marks a turning point. It brings the kind of AI assistant many hoped Apple would deliver years ago (one that actually performs actions, not just gives polite answers). ChatGPT could soon manage apps, automate complex workflows, and handle everyday Mac tasks in a way that makes Siri’s current abilities look… well, nostalgic.

Apple’s own Apple Intelligence still trails behind in scope. Siri’s major revamp, initially promised for 2024, is now delayed until 2026. That leaves a gap, one OpenAI seems ready to fill. Apple’s strong focus on privacy keeps its AI grounded on-device, while OpenAI can move faster with cloud-driven features. As a result, Mac power users might get their smartest assistant yet, just not from Apple.

This is what Vidichi wrote when testing Sky:

At the same time, Sky allows power users to make their own tools that combine custom LLM prompts with actions powered by Shortcuts, shell scripts, AppleScript, custom instructions, and, down the road, even MCP. All of these custom tools become native features of Sky that can be invoked and mixed with natural language.

That single quote sums up the difference in approach. While Apple perfects its ecosystem under tight privacy controls, OpenAI is building flexibility with an AI layer that connects with the core of macOS. If Apple doesn’t speed up Siri’s evolution, ChatGPT might soon feel like the real assistant Mac users always wanted.

Final Thoughts

Well, this story turned out quite interesting. It’s great that we, along with you, already have at least a rough idea of what the final result may look like. We’ve seen Sky in previews, some even had the chance to test it (unfortunately, we somehow missed that part, our bad). So now we wait for the next announcements from OpenAI, hopefully with the release of the actual tool.

As for Apple, we hope this event will give a strong boost to Apple Intelligence, so it actually works as it did in the promo (the one later deleted). Because, as far as we remember, Apple’s promises looked almost identical to the functionality shown in Sky. At the same time, we hope this becomes a push, not pressure, so Apple doesn’t rush to announce something again and end up with nothing concrete.

We believe in OpenAI’s potential, we believe in Apple’s power, and we’ll keep watching what both sides do next.

Jeff Cochin
Author
Jeff Cochin has more than ten years of experience in data recovery, management and warehousing. On Macgasm he mostly writes about Apple news and software reviews. Jeff's journey with Macbooks began in 2008, showcasing his enduring commitment to the Apple… Full Bio
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