There's definitely value in the space, but I struggle to imagine how the ends (capturing that value) justifies the means (how they're pursuing that value).
If you know your way around CalDAV [1], you can build the most valuable 20% of their features in a weekend. A team of 3-4 could build the most valuable 80% in a month or two. In fact, some people have not only done that but kept going, and we have FOSS tools like https://cal.com as a result, that are arguably easier to use.
As a board member/founder/executive, one has to in the mirror each night, and feel confident saying "I'm running this company responsibly".
Especially if you're working in a purely digital space (which Calendly is), you have to bend really far to justify hiring that many people. IDK, maybe I'm a standard deviation or two away from norms on frugality, but this baffles me.
[0]: To contrast, WhatsApp sold in (!) 2014 (!) with 32 engineers (~50 total heacount), servicing 450mm active users. So, Calendly have 10x the headcount, on .2x the valuation.
Massive addressable market, pretty mediocre state of the art, problem that people already spend real money to solve (poorly). $3B is high, but I can see a world where it’s justified.
Employee count seems high but I would imagine a disproportionate number are sales/marketing because, again, addressable market is huge and competition is fierce.
Postman… the addressable market is just not that large, especially for the features you actually pay for.