I worked at a startup that found it's traction competing against Calendly when it was already well established. Company eventually made it over $3m ARR and the

I worked at a startup that found it's traction competing against Calendly when it was already well established. Company eventually made it over $3m ARR and then started expanding into other functionality and today, is very, very different from Calendly. I was chatting with the COO a few months later and he said that the key is that you just have to be "1000x better" (exaggeration for emphasis) than the competitor in some key way. In the case of Calendly, the problem is how clunky it is. The gist of it is that yeah, you can't compete against the multi-million dollar incumbent directly, but you can do one thing way better than they do and that might be enough to pull away some customers.