A successful IPO has no necessary correlation to having crossed the chasm.
You've successfully crossed the chasm when you are the clear market leader in the a "mainstream market" segment.
In Twilio's case, that would be Being at the center of communications infrastructure for Fortune 500-1000 companies.
They've made some inroads (ING, etc). But most larger enterprises are still using Cisco/MSFT/Avaya and other on-premise tech for call centers, conferencing, video chat, collaboration, etc.
Also: Twilio is not profitable and it just lost one of its highest volume customers (Uber) who had been using it for "point solution" use cases, mostly around automated SMS and voice.
So if you disagree, that's fine. I'd find it much more productive to know what you disagree with and why than the ad hominem accusation that I'm a "bitter former employee" which is a. Not useful and b. False.