There seems to be a chain of events that causes the bug. I just got the achievement by:
0) starting as an Investment Banker
- b-line to her office.
- Turn off the wi-fi in her personal cafeteria,
- when she sits down, turn on the gramophone and retreat back to the coin displays.
*) If she gets a question mark above her head, she’ll be distracted.
**) Make sure to save as she doesn’t always check out the reward!