Risk & Resilience

The Only Woman in the Room

Kirsten Wolberg

11.08.21

Kirsten Wolberg has led companies in tech and finance - two industries typically dominated by men, especially at the leadership levels. Her take on leading, especially as a woman, is hard-earned and insightful.

Summary:

Kirsten Wolberg has led companies in tech and finance – two industries typically dominated by men, especially at the leadership levels. Her take on leading, especially as a woman, is hard-earned and insightful.

Thuy

Your experience is pretty unique among women leaders. You have held senior tech positions at PayPal, at Salesforce, Charles Schwab, and most recently at DocuSign. Senior leadership in tech is primarily made up of men, you know that, so I would imagine there were many times when you were the only woman in the room, what made you want to pursue this professional path? And were you guided by some kind of greater purpose?
Kirsten_Wolberg

Kirsten Wolberg

I started my career in financial services, another male dominated industry. So, I think that the experience I had coming through financial services and learning to find my voice in rooms full of men in that setting was ultimately what helped me get into technology.

Thuy

Was there ever a point during that journey, though, where you thought, why am I in such a male dominated field to begin with? Wouldn't it be easier to do something else?
Kirsten_Wolberg

Kirsten Wolberg

I definitely have that feeling. And I think it was the move when I went from Schwab to Salesforce that I really started to question, what am I doing? This is not easy at all. And it…

Thuy

Did you think about though when you were at Salesforce, was it something about the culture? Was it just the difficulties of often being the on the woman in the room?
Kirsten_Wolberg

Kirsten Wolberg

I think it was more the culture of the organization. Salesforce is a very strong engineering culture and I actually didn't come to technology through a engineering path. I found that being the only woman in the room and being a woman in tech became harder the more senior I became. And so Salesforce was my first C-level role. I learned after I accepted the position that no one had survived in that particular role at Salesforce for longer than nine months, it didn't matter your gender. It was a really difficult role. And because nobody had really been in that job for any period time, what happened was my peers kind of took a step back when I joined because their experience was that person is not going to be in that role very long. So, we're just going to kind of not invest in that relationship because, it's probably not going to endure. I felt very alone. That was the first time where I was like, wow, I am really doing this by myself.

Thuy

So, then how did you deal with that? Because this is probably a wonderful teaching moment for so many other women leaders and leaders of all types actually.
Kirsten_Wolberg

Kirsten Wolberg

So, the way I dealt with it really was to really focus on my team. So, when I started, I only had men on the leadership team and I quickly went about making the changes that I needed to make. I had 50% women on the team, 50% men on the team. I had ethnic diversity across the board and I just became really, really proud of this team that I had built. And we started to do great things.