Tejada, who previously served as CEO and president of Keynote Systems, and Wassenaar, who has held jobs as CEO of Airware and CIO at New Relic, met at a tech conference and forged a professional bond that, they say, shows how crucial networks can be for women and people of color. They spoke with Fast Company about their paths to power, and the role of mentors, sponsors, and good industry contacts. Edited excerpts follow.
Fast Company: Jennifer, how did you get your first CEO gig at Keynote Systems?
Jennifer Tejada: My career is quite unconventional [among] people who lead deep tech companies. I started at Procter & Gamble in brand and sales and marketing. Eventually I learned a lot about supply chain, and I ended up at a supply chain automation company in the late ’90s. I came into tech as a marketer, as opposed to a technology person. Around 2010, 2011, I was working for a CEO named Greg Clark, who went on to be the CEO of Blue Coat and Symantec. And Greg sat me down one day and said: “You know, you’re basically running the company as the No. 2, but I essentially get the credit. And it seems like you should be a CEO.”
I had a list of reasons why I either wasn’t ready or didn’t want to be the CEO at the time. I had a young baby. I had a husband that was also a leader and traveled significantly. And I really felt like being able to delegate some things and not being where the buck stopped was a good fit for me. [Clark] actually convinced me that leading the company allows you to set the clock and allows you to build the company and the culture around the way you work best. He started putting my name in the ring for CEO jobs.
But it didn’t happen right away.
JT: The first CEO gig is a hard gig to get, because nobody likes to bet on a first-timer unless they come highly referenced. We discount people who haven’t done a role before, even if they have more than enough qualifications, and as women, we often discount our own qualifications. When you think about the difference between a mentor and a sponsor, a sponsor is someone that is connected, who has visibility into powerful networks where opportunities live, and will actually make you visible as a candidate and will advocate for you.
Yvonne, how did you get the CEO job at Puppet?
Yvonne Wassenaar: My path was not too dissimilar. My first CEO gig was at a startup where I went over to be COO and two weeks into it they came to me and said, “No, you should be CEO.” And I had the long list of all the reasons why that was a bad idea. I have three kids. John Chambers [the former CEO of] Cisco happened to be on the board, and he sat me down and he said, “You’re more ready than you realize, and I’m going to be your wingman.” You need somebody who’s going to sponsor you, but you need that self-belief. And part of what holds us back is that there’s not enough of both of those things.
My first CEO gig was a great learning experience. I was trying to figure out if I wanted to just do board work or take another operating role. And then Jenn sent me a very innocent text. It just said, “Hey, there’s a really interesting company looking for a CEO. And I’m a huge fan of the folks running the search. Would you talk to them?” She didn’t tell me what company it was. She didn’t tell me that she was on the board. She just said, “I’d love to introduce you to these people if you would consider talking to them.” I naturally said yes, and that comes from the fact that I deeply respect Jenn. I trust her.
Jennifer, what made you reach out to Yvonne about the Puppet CEO job?
JT: I remember where I was standing when I sent that text. I was standing out on the patio in my backyard. When you’re a board member responsible for a leadership transition, you feel the weight of making sure that the company you have oversight responsibility for is transitioned from good hands to better hands. I wanted someone for Puppet who was technical, but who had heart, who could expand the vision, and who could build on top of the culture and scale the company. That’s hard to find in a single person, but I had seen Yvonne really flex muscles, coming from a large company background, being the CIO at New Relic, and then going to this sort of high-growth startup. But I didn’t know if she would take another CEO gig.
In recommending Yvonne, was part of your motivation to make sure that there was a strong female candidate on the slate?
JT: I have an almost relentless perspective on final slates because I don’t think one diverse candidate is enough. I think half the final slate needs to be diverse and underrepresented for a diverse or underrepresented person to even have a fighting chance of being selected.
Yvonne, are you frustrated or bewildered that we’re still having these conversations about diverse slates, and that people like you and Jennifer still need to speak up on it?
YW: Frustrated? Yes. Bewildered? No. People have good intentions, but we’re not moving the needle. There are two challenge areas that jump out at me, particularly when we’re talking about high-level roles. The first is that you have to be tied into the quote, right networks, unquote. Most of the C-suites and boards are run by white men, and so when they go and they brainstorm who should be on the slate, they think [of] the people they know. Unless you have diversity in that room, it’s highly unlikely that you’re going to get diversity on that slate. And even if you do, there’s unconscious bias throughout the whole process. Take somebody like me. I have 13-year-old twins and a 15-year-old daughter. There’s an immediate assumption about how much I’m going to want to travel. I’ve programmed in assembler, Pascal, and I started my career as a software engineer. Yet people would come up to me [when I was at New Relic] and say, “Wow, CIO, that’s a really technical job. How did you get that?” There’s just layer upon layer upon layer of unconscious bias.
JT: When I insist on a balanced slate, it means the recruiting process will take longer. And I am the same annoying leader who’s also saying we’ve got to hire fast, we’ve got to grow. I expect my leaders to just manage that paradox. That is just part of the gig. When we decided to open another location in North America a couple of years ago, one of our top three criteria for a new office was to create access to careers in the tech industry for underrepresented people. We ended up launching an office in Atlanta, which has been a huge business success. Atlanta produces more underrepresented undergraduate engineers than anywhere else in North America. You can [diversify your workforce] and drive further and faster at the same time.
YW: I wanted to diversify my board as it related to people of color, particularly black leaders. I looked at my own network, and I didn’t have a lot of black leaders, but I had a couple. I went to them and they introduced me to some people, who introduced me to other people, and all of a sudden this whole valley of unicorns appeared. They invited me in because I had true intent to actually make a difference.
Sometimes you have to test limiting beliefs. “Gosh, can someone who’s never been a CEO before be a CEO?” Well, somebody had to do the first time. On my board, of the four members I added, three had never served on a board before.
JT: I believe representation on the board is super important. I know that the black community within PagerDuty felt very strongly that they wanted to be inspired by seeing a black person on our board, by having someone who sets an example and who is looking out for that community as a part of, of their directorship.
Yvonne, how did you and Jennifer first meet?
It was in San Francisco, at a Girls in Tech conference, and Jenn was the speaker before me. One of the nice things when you’re on the speaking circuit is you do get to meet these other amazing leaders. I could text Jenn and be like, “Hey Jenn, I’m raising money. Do you know so-and-so?” She was somebody who would always get back to me. And she could reach out to me and say, “I’m back-channeling this person—do you know them?” That real kind of support of each other is critical.
You’ve talked a lot about the power of networking, which women and people of color can find difficult. What’s your advice for professionals from underrepresented groups—or individuals who just really hate doing it?
YW: But the best advice that I got from one of my male colleagues was: networking is part of your day job. There’s this belief networking has to happen after hours and on the weekends, and as a single mom with three kids, that’s pretty hard. And my male colleague looked at me and he said, “Yvonne, you eat your lunch at your desk. At your level, part of your job is networking. It helps you get information, make relationships with future talent.” I think it’s really important that we give ourselves permission, particularly early in our career, to know networking isn’t extracurricular, it’s part of your day job. And the more senior you get, the more that you should be doing.
JT: I sucked at networking for most of my career. I actually dismissed the importance of it for a long time. [I didn’t appreciate it] until I had been living in Australia for 12 years and came back to the U.S. and nobody had ever heard of me in Silicon Valley. If you think about your network as currency, you approach it very differently than if you think of it as a necessary evil or something that you have to do in order to get ahead. The other thing is, like any other form of currency, you have to invest in it to get [something] out of it. So a lot of my networking time is spent helping others.
YW: Jenn and I aren’t personal friends; we don’t hang out or get-together with our families. But we’re great professional friends. I can always call on her for anything, and she will help me out, and I will do the same. Most people assume that, you know, women network personally, and we must get our hair done together. We don’t. Jenn and I network professionally—I’d do anything for her and she’d do the same for me.