What PayPal’s VP Of Technology Learned From Facing Adversity

Kirsten Wolberg’s career was sidelined by a family illness. Now back in the saddle, she advises women to be unique and seek out mentors.

What PayPal’s VP Of Technology Learned From Facing Adversity
[Beautiful girls: Olesia Bilkei via Shutterstock]

Kirsten Wolberg had a career plan. She’d studied finance at the University of Southern California and worked for several banks, finding employment as a management consultant and project manager before landing at brokerage firm Charles Schwab.


But then life threw Wolberg a curveball. Doctors diagnosed her husband with stage 4 cancer while she was pregnant. She took several months off work to care for her family. When she returned to the office, she interviewed for a technology position with Charles Schwab that cemented her path in tech.

Today, everyone’s doing well.

Fast Company spoke with Wolberg, now vice president of technology for San Jose, California-based PayPal. While she says her husband’s illness was one of the unluckiest things to happen to her family, making her own luck out of a difficult situation was critical to her career.

Wolberg reveals to Fast Company about what she wished she knew when she was first starting out, and what she’s learned along the way.

1. Embrace Who You Are

Wolberg says it’s important for women, particularly in a traditionally male-dominated field like technology, to embrace who they are and what makes them unique. She says it’s important to not “try to out-man the men.”

Early on, she reflects, she wore an Oxford button-down shirt with a silk bow tie, trying to look–and act–like a man. Wolberg soon realized that by trying to be more masculine, she wasn’t embracing the skills and capabilities that are intrinsic to being a woman, such as teamwork, empathy for customers, and an inclusive communication style. After that, she abandoned the bow ties and put her skills to work.


2. Treat Yourself As You’d Treat Someone You Admire

When you admire someone, you listen to what they’re saying, Wolberg notes. She says women especially need to give themselves permission to have a voice, a point of view, and to express themselves at meetings.

Everyone has a unique view they bring to the table, she says. It’s important to evict the negative roommate living in your head that keeps you from speaking up.

3. Find Your Supporters

“It’s so important for women to seek out and find mentors and sponsors,” Wolberg says. Wolberg adds her first boss created a job for her in a new company, and her sponsor at Schwab believed in her more than she believed in herself at times.

The importance of finding the right sponsor or mentor can’t be overstated, she says. What’s the difference? Wolberg explains a mentor can offer situational advice from time to time, whereas a sponsor has an added interest.

“[Sponsors have] a vested interest in the success of your career, and will go the extra mile for you,” she says. “A sponsor is actively looking for the next role with you and doing what they can to influence and create that opportunity.”


About the author

Lindsay LaVine is a Chicago-based business and lifestyle freelance writer who's worked for NBC and CNN. Her work has appeared online in,,, NBC News, MSNBC, Yahoo, Business Insider, and Fox Business.