Getting Past The Glass Ceiling With Kirsten Wolberg

by | Apr 30, 2020 | Podcasts

SWGR 519 | Breaking The Glass Ceiling


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.

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Getting Past The Glass Ceiling With Kirsten Wolberg

Advice From A Tech CTO

You are about to hear an interview with Kirsten Wolberg, who is the Chief Technical Officer at DocuSign, and also does a great deal about mentoring younger people, especially women on how you get to the C-Suite. She got to talking about what we can control and what we can’t. Fearlessness, confidence, going 85 miles an hour while you can in case maybe you don’t have to earlier and how we model ourselves on the people around us. If you find good people around you, that will make all the difference. I’m honored to have Kirsten in this episode.

This is the podcast where we talk about the craft of live communication. This is where we interview experts about how we show up, how we present ourselves and how we can get people that we’re talking to, people who are listening to us to do what we want them to do. That means getting the result that you want whether you’re speaking in a meeting or on a stage or one-on-one conversation. It’s all about how you present yourself to get the right result. Before we begin, I’d like to invite you to go over to our free assessment, which is You could take a 3 to 4-minute assessment that will help you see where your presentation skills are strong and where maybe you could use a little bit of support. I am excited to have the amazing Kirsten Wolberg. Thank you so much, Kirsten, for joining us.

It’s great to be here.

Kirsten is a highly sought-after speaker. She has lots of experience. The important part is that she’s a seasoned leader at the cross-section of technology, cybersecurity, digital transformation and talent management. She’s got a distinguished track record at leading technology and talent at global companies including DocuSign, PayPal, Salesforce and Charles Schwab. She’s a board director of SLM Corporation and Sallie Mae Bank. Prior to Silicon Graphics being sold to HP Enterprise, she was a board director there. In November of 2017, she joined DocuSign as the Chief Technology and Operations Officer.

She speaks frequently in the industry on innovation, payments, technology, cybersecurity, agile development and especially women in technology. That’s where we’re going to focus is how women can get past the glass ceiling. She knows a lot about that part being a C-level executive. She was recognized in 2016 as Computerworld Premier 100 Technology Leaders Master of Disruption and as an IT Rising Star. She’s also been named one of the Most Influential Women in Business in the Bay Area in 2011 and 2018 by the San Francisco Business Times.

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In addition to all the stuff that she does professionally, she’s committed to the organizations that help at-risk or underserved groups find sustainable long-term employment. She’s a founding board member at Year Up Bay Area and Vice President of the executive committee from the board at Jewish Vocational Services. Kirsten, thank you much for joining us. This is a question I ask everybody. If you could interview somebody from history, who would it be? What would you talk about and who ought to be in the audience?

I would love to interview Amelia Earhart. She was a pioneer in aviation and she’d been distinguished as being the first woman to fly solo across the Atlantic. She had dozens and maybe even more records. She wrote books about her experiences. She was an early pioneer for women’s rights and believing that women could do everything that men could do. Sadly, when she was only 40 years old, in her attempt to fly solo and circumnavigate the globe, unfortunately, she disappeared over the Pacific Ocean. I thought about her for my historical interview because one of the things that I focus on when I’m talking to younger women and back on my career, what was a differentiator in helping me get through some of the barriers that came up along the way? The word I always come back to is fearless.

I have a phrase that I use with my girls. I have 19-year-old and 17-year-old daughters. What I say to them is, “Always be fearless. Always take risks and don’t be afraid of anything, but I want you to make sure that you stop yourself if you’re going to be doing something that you could kill yourself or somehow you could die.” Don’t take those risks. What’s interesting is this is a perfect example. Amelia took many risks and I’m sure she didn’t think that her embarking on this journey, she’d successfully had many solo flights in many ways. She took on this ultimate risk and she did ultimately die. I thought to myself, “I wonder what was in her head.” She was fearless. She was someone who could see the possibility and had done all of the right training to prepare herself to take on this challenge.

She went into it. I would love to be able to have the conversation about what was in your youth and in your formative years that gave you that confidence that gave you the fortitude to be able to break through all of the barriers you saw and you experienced along the way. Even more importantly, to set such high ambition for yourself and to be able to do so in a way that was risky because air flight was risky during hearing new. It wasn’t like the jets that we have. That’s who I’d like to talk to and what I’d like to talk to her about. I would love for all young women in the audience to hear and be inspired by her story and to do what I asked my daughters to do and be fearless and take risks. Short of those risks where you may lose your life.

It’s interesting because although what happened was she disappeared, thus spawning many books and movies, but before that last one, she took risk after risk. She risked failing, which is something that women tend to worry about. What happens if I’m wrong? What happens if I don’t do it perfectly? We don’t hear about the times that she tried and blew it and it didn’t work out. We only hear about the successes. How does that relate to women getting past the glass ceiling nowadays?

SWGR 519 | Breaking The Glass Ceiling

Breaking The Glass Ceiling: The differentiators for women are fearlessness and confidence, and that seems to come back time and time again when talking about women not being able to get past the glass ceiling.


Ultimately, the differentiators for women are around fearlessness and are around confidence that seems to come back time again around the controllable parts of women not being able to get past the glass ceiling. There are certainly structural things that are in place that are not controllable by an individual woman. Having that confidence and exuding that confidence. I often hear when I’m talking to the mentees in my organization and outside my organization, women tend to have this negative roommate that lives inside their heads that is saying all of the, “What happens if I’m going to look stupid? I’m not ready for this. This is too big of a stretch.” I call it the bad roommate because I like to say, “If you were living with that person who was saying those things to you, you would ask them to move out because they would be a bad roommate,” but because they are inside your head, you don’t ask them to move out. You let them live there and that is a big part of not leaning into scary stuff.

I don’t know about you, but mine mostly sounded like my mom so I can’t really throw her out. A lot of this sounds like my mom. That’s a good point. I hadn’t thought about it. I’m still living with my mom at age 60 plus. Can you talk about women getting into the C-Suite and on boards? What’s the difference? Is it different in tech? Is it different elsewhere? Is it because you’re in tech? Why do we talk about women in tech especially?

I’ll give this answer in two parts. Sally Blount, who was the former Dean of the business school at Northwestern Kellogg. She was the Dean for about 7 or 8 years. She did a whole body of research with several folks at Kellogg looking at specifically the question, “Why aren’t women moving through the different stages and getting to the board room?” She talked about a woman’s journey in three pivotal steps. The first is launch, not much in the timeline, but about your first ten-ish years. The second phase is a very appropriately named mid-career marathon. The third phase is around the executive transition. The body of research that the Kellogg researchers did demonstrate that you had to excel at each part of the journey. It was not a matter of getting to the C-Suite. What I’ll say is in that early launch to get yourself on a trajectory to be in the C-Suite, you need to have the highest slope in terms of a path of your career. You need to be getting to the next level as quickly as possible. You need to be getting the broadest amount of experience as possible. There are certain careers position you better to do that than others. Traditional careers like investment banking, management consulting, but also, in this world, it’s the fast-growing technology companies. Finding roles there because in those companies you’re dealing with the newest technologies, those companies, the growth in and of itself is giving you experiences.

As the company is growing, your job naturally grows with it. Oftentimes in those environments, you are asked to wear many different hats because you are in this rapidly growing environment, giving you a lot of opportunities to grow your skills and capabilities. You need to be going as fast as you possibly can coming out of the launch into mid-career marathon because this is where life happens. This is where you potentially have kids, you get married, you get cancer, your spouse gets cancer and your parents start aging and need to move into a facility. You have all these parts of life that you have to attend to. You have a career but you have to attend to these things and they may keep you from still going 85 miles an hour. To the extent that you are going 85 miles an hour going into the mid-career marathon, you can take your foot off the gas a little bit because you have these other things going on and still be going 50 miles an hour as opposed to if you enter this phase going 35, you’re going to slow down to five miles an hour.

Making sure you enter that phase going as fast as you can and once you get into that phase, it’s focusing on the differentiators. It’s taking risks, putting yourself out there for jobs that you might not quite feel ready for. It’s focusing on the skills of communication, influence and motivation. It’s finding a network of individuals who are a combination of sponsors and mentors who will help you be introduced to those opportunities. It’s also about becoming known for something and being an expert. That’s where the technology angle of your question comes in. I have become known in the marketplace as an expert in the things around technology, digital transformation and cybersecurity. As companies are looking at the challenges they face, many of them are facing challenges in these spaces and are recognizing in the faces, in the minds of those individuals who are sitting around the board table. They don’t have a representation that can speak with an expert voice to those challenges.

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One of the things is that to rise in a career, this is why I teach public speaking. When you’re up there speaking, it is a wonderful tool. It is a tool for marketing yourself. You’re delivering information, but also if you’re the person up there on the stage or behind the podium, you’ve got automatic credibility and then people say, “Kirsten Wolberg knows about that. Let’s ask her.” It brings you to people’s attention. I wish I’d known that at 25 because I spent years waiting to be noticed. I was great that my mother kept saying, “If you keep quiet, people will notice and you’ll be prompted for the worth.” No, it is not the case. 

An interesting story is, I’m on the board of Sallie Mae. The way I got that opportunity to interview for that board seat was through a panel I was sitting on. I was speaking on digital transformation and agile transformation and how to move from a more traditional development methodology to an agile methodology. After the panel and after the discussion, someone from the audience walked up and said, “Are you looking for a board seat?” I said, “I am.” My ability to convey my expertise through that panel keyed in this executive recruiter’s mind, this is the profile of a candidate that we’re looking for this board seat. I had a conversation with the executive recruiter on a Thursday. I flew back East on a Monday, interviewed for the role on Tuesday and was given the offer on Thursday.

For our non-American audience, can you quickly say what Sallie Mae does? What they are?

Sallie Mae is the largest student loan bank and holding company in the United States. Most people don’t realize that the overwhelming majority of student loans are government loans. Those got 93% of all of the loans that students get for education in the United States come from the US government. There is 7% of the loans that are given by private, not private companies, but non-governmental companies. Sallie Mae is the largest of the nongovernment student loans in the US.

Is that managing a lot of money?

SWGR 519 | Breaking The Glass Ceiling

Breaking The Glass Ceiling: You have to focus on communication, and find a network of individuals who will introduce you to the opportunities you need to succeed.


Yes. Over $5 billion in loans were granted.

You and I’ve done a lot of work with How Women Lead and Julie Abrams, which helps women get set up for board seats. Elsewhere on this podcast, we’ve got an interview with Julie Abrams about that. Could you in a couple of sentences say why it’s important to get women on boards? We’ll go back to talent management at a not quite board level. 

At the end of the day, the importance of getting women on boards is a broader statement of it’s important to have diversity on boards. We have seen through all of the research that diverse groups come up with better decisions, have better outcomes in a technology environment. When I look at a team, if I have women on the team, I get a 15% higher output from that team that if it’s all men.

That’s racial diversity as well and national diversity.

It’s not just gender diversity. We’ve started with in terms of the dialogue and the conversation with the gender diversity component, but it is much more broadly. How do we represent race, gender, sexual orientation, etc? I see it as age diversity. When you talk about the board level, we have a lot of boards that certainly are more senior than probably they should be. They’re all aspects of diversity art, it important at the board level.

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Going back to below the glass ceiling, I spent 30 years in the upper business wanting to run an upper company and I kept getting to the shortlist and watching the job go to a man. It wasn’t until I started working with business and I said, “That was a glass ceiling I was hitting. I thought it was something wrong with me.” It’s a typical female thing. Talk a little bit about the talent manager. You talked about going 85 miles an hour while you can. I want to say DocuSign has been nominated as the third Best Place to Work by Glassdoor. Is that all of America or is that international?

I believe that Glassdoor does have some international companies, the majority of their databases of the companies that are represented are from the US but they do have some multinationals. We are super excited about that because we do work hard at DocuSign to make sure that we are creating an environment where you can do the best work of your career. The diversity and inclusion components are incredibly important to us. Our CEO, Dan Springer, came in and we had one woman on the board and we had no women on the executive team. We have four women on the board and we have three women on the executive teams. He puts his money where his mouth is. He doesn’t say the right things, he does the right things.

As a company that’s part of our value set in making sure that we are creating an environment that everyone can succeed and thrive and the talent management pieces. One of the things that when I was working at PayPal, they had a rotation program for executives to allow them to learn other parts of the business. I was asked to move into a rotational role for eighteen months in the talent organization. I have to say when I was approached, my response was, “That’s unexpected.” A woman who’s been in technology and operations most of my career. I was like, “Okay.” It was a great experience. It was a challenge. I was further away from the business than I’d ever been and that was a difficult transition for me.

It was a different work than I was used to the employees that were in my organization had a different mind frame and a different mindset, different education and experience. I wasn’t working with a bunch of engineers and engineers are problem solvers. They are trained to solve problems and to think in certain ways and be analytical and be data-oriented. I didn’t find that to be the stereotype or the prototype of an employee within the HR organization. It was that mid-career marathon piece of you need to get as many experiences as you possibly can. What I didn’t know at the time is how valuable that particular skillset was going to be vis-a-vis a board seat.

Many of the topics that come to the board are people-related and the nom-gov committee, which I sit on for Sallie Mae. It’s nominations and governance. With nominations is we also look at all compensation issues and succession planning. A lot of the HR-type of responsibilities of the board does go into nominations and governance or a compensation committee structure. Having that direct experience as a line manager in that function puts me at a unique advantage in a board room and those nom-gov conversations because I’ve experienced it at an operator level. It’s not something that I’ve observed, I’ve been driving and leading those types of initiatives.

SWGR 519 | Breaking The Glass Ceiling

Breaking The Glass Ceiling: In the past, the trick to success was to be like the boys. That tends to work for a while, but eventually, it’s not cute even in the slightest.


I’ve got one more question for you. You were talking about having to excel early on and one of the things we talked about a lot in this podcast is how women wait until they’re 100% ready and men are socialized from birth to go for it, even if they’re not ready. Back in my upper days, I used to get these arrogant young men who hadn’t yet failed. Their careers were on arise and they hadn’t yet learned that it was possible to fail and that you could then also survive afterward. Usually, the ones who were too busy talking have time to listen when their job was to listen to me. I know it’s a thing for women to go for it. You’ve said in the past that you used to think the trick was to be the boys and that worked for a while. Can you tell us a little bit about that? 

My career started in commercial banking in the ’80s. I was in banking which is a male-dominated industry. I moved into consulting predominantly for financial services. Again, it’s male-dominated. As human beings, we model our behavior after those around us. I’ve always been a bit of an overachiever. I sat in the front row, always raised my hand, did all my homework and got all As. I have that in my DNA and I didn’t lose that going from school into the business. I wanted to be the best. I want it to be the first in class. I watched around me, who was in that first in class position? In almost every case it was a man. I started to model those behaviors. I was trying to outman the men. I started dressing like a man. I started talking and swearing like a man. I started being aggressive in my behaviors, in my body language because I was trying to do the things that I saw others doing that were making them successful.

While I was young and while I was far below those individuals’ level of power, they all thought it was cute. I was adorable trying to be all professional and stuff. It wasn’t until I got to a place where suddenly I was at a peer level where these behaviors appear or right below that peer-level where these behaviors suddenly became seen as being aggressive and threatening. It stopped being cute even in the slightest. At this point, everyone’s read a ton about it. The language about being too aggressive, being too abrasive was another word I got. I heard too ambitious a lot. That started to be something that was holding me back. I was seen as having user-interface issues where the same behaviors on a man were seen as being positive behaviors. I don’t know that I would have recognized it without external intervention.

It was a series of happy accidents of things that came into my life all at the same time. It made me realize that authentic leadership does start with self. I am a woman. I am proud of being a woman. I know that I have unique gifts, skills and capabilities as a woman that I wasn’t allowed out because I was modeling something that wasn’t authentic. That shifted for me. I almost always only wear dresses. I dress like a woman. I lost most of the profanity from my conversation and I leaned into those more nurturing aspects and more vulnerable aspects of my personality and realized, “This is the difference and this is where I was holding myself back.” As you step into yourself, as you truly let your authenticity be the lead, that’s for me when the shift happened and opened up a lot of career opportunities that I wasn’t seeing otherwise.

It’s one of those things that in some ways, you’re damned if you do, damned if you don’t. I call it walking the tightrope between respected and being called bossy and abrasive. You do have to assert your authority, but you can’t do it bearing in mind that rule number one in speaking. It’s all about your listeners and how you’re being perceived. You have to put yourself in their shoes and say, “There are things men can get away with that women can’t. It just is.” It’s the way we’re socialized. One would hope that, when we were marching in the protest marches with Gloria Steinem and all of that, we would have fixed it. This is a new wave of it. Kirsten, this is amazing. I don’t want to let you go. I know you have an incredibly busy day. I’m thanking you much. If you had one thought to leave for our readers, what might it be? 

Be fearless: take risks and don't be afraid of anything. Share on X

The phrase I always come back to is tied to the conversation we had which is, “Honor your feminine.” I had an opportunity to participate in the Hello World Project, which was an opportunity to write something on my body and have the portrait taken. That’s what I chose to write, “Honor your feminine in my Hello World photo because it’s a message that women need to celebrate their femininity.

For the men who are reading, it’s mostly women, but we do have men reading. Do you have one word of advice for the men?

Learn to be an ally to the women in your life to enable them to achieve the level of power and influence that men have been able to have in the past and the present.

That men take for granted because we socialize that way. Kirsten Wolberg, this has been such a delight and an honor to have you with us. Thank you much. I will see you at the next one.

Thank you so much.


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About Kirsten Wolberg

SWGR 519 | Breaking The Glass CeilingKirsten O. Wolberg is a seasoned leader at the cross section of technology, cyber security, digital transformation and talent management. She has a distinguished track record leading technology and talent at global companies including; DocuSign, PayPal, and Charles Schwab. Kirsten is a current Board Director of SLM Corporation and Sallie Mae Bank where she serves on the Risk Committee and the Nominating, Governing and Compensation Committee. Formerly, prior to the company sale to HP Enterprise, Kirsten was a Board Director at Silicon Graphics International (SGI), where she served on the Audit Committee. In November, 2017 she joined DocuSign as Chief Technology and Operations Officer.

Kirsten is a frequent industry speaker on innovation, payments, technology, cyber security, agile development and women in technology. She was recognized in 2016 as Computerworld Premier 100 Technology Leaders “Master of Disruption” and as an “IT Rising Star”. Kirsten was named one of the Most Influential Women in Business in the Bay Area in 2011 and 2018 by the San Francisco Business Times.

Kirsten is committed to organizations that help at-risk or underserved groups find sustainable long-term employment. She is a founding Board Member of Year-Up Bay Area, and Vice President of the Executive Committee of the Board at JVS, (Jewish Vocational Services).

She holds a BS degree in Business Administration from the University of Southern California and an MBA degree from the J.L. Kellogg Graduate School of Management at Northwestern.