> The CEO at my last company (2022) refused to use Let's Encrypt because "it looked cheap to customers".

Spoken like a true dinosaur. How can a certificate based on open, public and proven secure protocols be cheap?

> So my question: has anyone actually commented to you in a negative way about using Let's Encrypt?

No, but I personally judge businesses which claim to be tech savvy if they don’t have an ACME issued certificate, because to me that instantly shows I’m not dealing with someone who has kept up with technology for the last 10 years.