At another company in 2015, I discovered we were sending user credentials for a large hospitals in plain text across the network and need to fix this ASAP. When I brought this up to management, they shrugged and said "it's been this way for years and we have other priorities". After a large New York hospital was breached, I suddenly had management show up to my desk in panic asking how we can fix the issue immediately. I came up with a nice write-up for both our company and the hospital IT groups on how to secure our infrastructure with certs and whatnot and they still half-assed it with self-signed certificates.
In 2018 I worked for a fin-tech company in charge of some A-list celebrity 401K portfolios. We had a default admin password for our production database. ZERO encryption on the data; including SSN, birth-date, phone numbers, addresses, beneficiaries info, etc.
Last year one of the leading payroll providers in the country (USA) I used to work for started aggressively out-sourcing the software and allegedly had a really nasty security breach due to a back-door inserted by one of the out-sourced team members. It's alleged that leadership threatened employees if they disclosed the incident to anyone outside a key group of members.
Nobody give a damn about security until their identity is stolen and they have to spend hours/days/weeks/months putting their lives back together from the fallout.