Calendly changed its main positioning in 2024 for the first time in 8 years.

Our quick definition of positioning:

Positioning = target market + differentiation

Between 2016 and 2023, Calendly was primarily positioned for individuals and companies that were scheduling meetings using back-and-forth emails (their "target market").

During these seven years, many other scheduling tools came on the scene, trying to grab pieces of the market Calendly had so adeptly created and captured.

I don't have insider information on the conversations happening within Calendly leadership, but my guess is that the sales teams were hearing more and more about other competitors in deal cycles.

And likely, Calendly's account executives were having to do much more objection handling when pitching Calendly vs. the other platforms.

No longer were the conversations "here's why Calendly is way better than sending emails..."

...now it's likely "here's why Calendly is so much better than Chili Piper, EasyCal, etc."

Believing that the market and category had sufficiently matured, they made (the likely difficult) decision to no longer position against back-and-forth emails, but directly against the vendors in the "scheduling tools" category.

Did they make this shift too late?

You could potentially argue they should have done this sooner, as the up-and-comers continued to still market share.

But you could also argue that they've made this shift too early.

There is likely still a very large portion of the business world that is still using back-and-forth emails to do their scheduling (and has never heard of Chili Piper or any of the other 50+ scheduling tools).

Internally, Calendly's leadership has done the calculus that it's worth focusing on the more mature market that 1) knows what scheduling tools are and 2) is potentially evaluating or using those tools already.

Time will tell!