Can startups make scheduling less terrible?

There’s only one thing worse than sitting through meetings: scheduling them.

In theory, scheduling is a simple task. But now that we’re in an age of endless Zoom check-ins, phone calls, and team meetings, syncing a calendar often isn’t as painless as it should be.

A handful of startups are trying to end our misery

Everyone in Silicon Valley wants to disrupt the calendar:

• Clockwise ($31.4m funding) uses AI to move around your meetings to avoid overlap and create more “focus time.”
• Superhuman ($33m) trawls through your email for key phrases, like “tomorrow at 3pm,” and whips them into calendar events.
• ReclaimAI ($1.5m) lets you assign different levels of priority to your meetings (so if someone wants to book you for that 1pm slot you dedicated to The Sopranos, ReclaimAI will just bump your Tony time to the evening).
• Calendly ($350k) shows your available times and asks people to book you to avoid the ol’ back-and-forth. Sending your Calendly link is also a power move: You’re saying, Look over my schedule, pleb, and find your own space.

Do we have to brace ourselves for calendar influencers?

Some players in the calendar space are even trying to make scheduling — dare we say — fun.

The startup IRL has raised $11m with the mission of building a social calendar platform, where you check the calendars of hip people who live near you. It’s kind of like Instagram meets scheduling.

The next frontier in the digital calendar arms race could very well usher in a new class of “calendar influencers” who hype up virtual Megan Thee Stallion concerts just by adding them to their public plans.