For so long, the glass ceiling is something that has existed for women, no matter what environments they were in, or what they were doing, and it has severely limited the opportunities that those women receive. But more recently, more and more women have been able to put in the work in breaking the glass ceiling, ensuring that they - and the women that would come after them - could advance safely and surely. As the Chief Technical & Operations Officer at DocuSign, Kirsten Wolberg has many ideas about how women can get past the glass ceiling. She talks with Elizabeth Bachman about how to deal with doubt, who to surround yourself with, and why being "one of the guys" worked - until it didn't.