Whitehead, who is currently the CEO of her fourth company, The Pink Ceiling - an organization that offers consulting, seed investing, and commercial support for startups that affect women - recently told Adam Bryant of The New York Times:
"I have this wish to never go above 50 employees. Above that, there is a shift in the personal interaction you have with them. Below that, I can still remember your dog's name and whether you just had a baby. At a certain size, you lose some of that.
"I love knowing everybody. My quirk is that I nickname everybody who works for me, and I don't know if I can nickname 250 people the same way I can with 50."
When Bryant asked Whitehead how she comes up with nicknames she explained that they usually come from stories employees share with her. "There will be something that is very memorable that totally captures them. It becomes a big thing the day you are nicknamed, and everybody knows the story behind why you get that nickname. You can literally go to company events and we only call each other by our nicknames."
Her nickname, she said, is "H.B.I.C."
"They have promised me it stands for Head Betty in Charge, but I'm pretty sure that's not what the B stands for," she told Bryant. "But it's out of love. My business card says Head Betty."