Yes?
Try abacus, slide rules or mechanical calculating machines vs electronic calculators.
Or ancient vs modern computers and software. They didn't even have "end-users" like we understand them now, every computer user was a specialist.
Programming.
Writing. Quill vs. ballpen, but also alphabets vs what you had to write before.
Photography, more than one big jump in usability. Film cameras, projectors/screens.
Transportation: From navigation to piloting aircraft or cars. Originally you had to be a part-time mechanic.
Many advanced (i.e. more complex than e.g. a hammer) tools in manufacturing or at home.