Software Applications Incorporated, introducing their new Mac app earlier this week:

Sky floats over what you’re doing so AI is always at your fingertips. Whether you’re chatting, writing, planning, or coding, Sky understands what’s on your screen and can take action using your apps.

The company is founded by Ari Weinstein, Conrad Kramer, and Kim Beverett, three Apple vets. Weinstein and Kramer were the team behind Workflow, which Apple acquired and turned into Shortcuts. App Intents—an integral part of the since-delayed “more personal Siri” Apple Intelligence feature—came from the work the Shortcuts team did.

Federico Viticci at MacStories wrote a comprehensive preview of Sky:

What sets Sky apart from anything I’ve tried or seen on macOS to date is that it uses LLMs to understand which windows are open on your Mac, what’s inside them, and what actions you can perform based on those apps’ contents. It’s a lofty goal and, at a high level, it’s predicated upon two core concepts. First, Sky comes with a collection of built-in “tools” for Calendar, Messages, Notes, web browsing, Finder, email, and screenshots, which allow anyone to get started and ask questions that perform actions with those apps. If you want to turn a webpage shown in Safari into an event in your calendar, or perhaps a document in Apple Notes, you can just ask in natural language out of the box.

The whole piece is great, providing both explanations and context for the features of the app. Viticci is a longtime fan of both Workflow and Shortcuts, and it’s fitting he gets the honor of writing the first major story.

Sky looks right at home on macOS. In fact, everything Sky is doing seems completely aligned with what macOS and Siri should be doing—it’s functionality that should be built right into the system. In several ways, it mirrors what Apple announced at WWDC would be possible with that “more personalized Siri,” including reading what’s on the screen to provide “context-aware” behavior.

That it’s not part of macOS makes me wonder why Weinstein and team couldn’t build it while at Apple. Weinstein was certainly on the right team (Shortcuts and Intents) to do it, and obviously had the vision and technical chops to pull it off.

The short window between Weinstein’s departure from Apple and the first interview where he shared the plans for his new company—about five months—is at least suggestive he’d floated the idea inside Apple… and received a cool reception.

Regardless, I’m guessing some executive inside Apple is kicking themself now—and possibly plotting how to acquire Weinstein and team, for the second time.

(They may have competition: The app relies on OpenAI’s ChatGPT, and OpenAI’s Sam Altman is an investor in Weinstein’s company.)

I’ve signed up for early access. While generative AI has many, many (many!) issues, it also offers tremendous potential.

I first met Ari when he was a WWDC student award winner; I’m pretty sure he was still a teenager in high school. We chatted for a bit in the labs, and I remember coming away very impressed. We caught up a few times over the years at the conference, and when he showed me Workflow, I was blown away. I was very excited for him and his Workflow team when Apple acquired them—and excited for Apple. I remember thinking he would go far inside the company. He was smart, focused, and ambitious. His team and mine worked together a lot over the years, and I remained impressed by his drive and leadership.

It saddened me when I heard he left Apple. When he launched Software Applications (a fantastic domain and terrific site!), I very nearly reached out to him with an offer to invest in whatever he was doing—before seeing he’d already raised $6.5 million from Sam Altman and others.

Which is to say, I have sky-high hopes for Sky.