When Chelsea Grayson first accepted the role of general counsel and chief administrative officer with troubled retailer American Apparel in late 2014, she couldn't have known that someday she would find herself preparing the company for a sale after its second bankruptcy and then taking the helm as chief executive officer.

Grayson's tenure as GC began after Dov Charney, the apparel company's founder and CEO, was ousted from the company over allegations of sexual misconduct. She led American Apparel through a turnaround after the retailer filed for Chapter 11 bankruptcy and resolved lawsuits with Charney. Grayson found herself as a candidate to step into the CEO role after his replacement, Paula Schneider, decided to leave the company. In an interview at the time, Schneider detailed how in her time with American Apparel she received death threats and needed a bodyguard to go to work.

Grayson didn't feel the same toxicity within the company and accepted the CEO role last September. But despite the new title, she didn't take off her lawyer hat that quickly, as she was immediately tasked with selling the company after a second bankruptcy.