I've gotten flack from my tech industry friends by stating that "executives handle IT" at small firms. For insurance, a small family office for financial planning. Type A personalities will onboard new hires themselves, even while working as a financial advisor. People who have "been out there" will back me up on this. How do you convince people (who have no time, but work like time is unlimited) to invest in dedicated IT resources? What convinced them to change?
I've found that the first time they are told they're screwed and have lost all their data because of a crypto ransomware attack or something like that is the trigger.
These types usually penny pinch at the worst places. Save a dime, spend a dollar, and all that. If it doesn't hit the pocketbook in a *direct* manner, it just gets pushed down the road.
On boarding new hires? That might not be so bad; implementing your tech needs without knowing what they are and having the time to upkeep it all? Not so good.