‘Risks Aren’t Risky’: Yvonne Wassenaar’s Unconventional Path to CEO

We all want to do work we love and make a difference in the world. But the path to that life isn’t always easy to identify—and it’s rarely a straight line.

So says Yvonne Wassenaar, a veritable rock star whose own path has traversed many roles: strategy consultant, software engineer, operating executive, CIO, and CCO. Now she’s CEO of Puppet and serves on the board of directors at Harvey Mudd College, Forrester, and Anaplan.

“I love when people ask me how I got to where I am,” Yvonne told us on a recent episode of the BUILDing To Boss podcast. “Because I think it’s so important to dispel the belief that people who get to the top have some master plan that’s all perfectly mapped out. There are absolutely those who fit that mold, but that certainly wasn’t my journey. So if you don’t fit that mold, don’t give up.”

As Yvonne made her way along the twists and turns of her career path, she relied on a few fundamental attributes:

• Intense curiosity. Yvonne found that her innate curiosity made her an agile learner who’s open to feedback. “I’m in an incredibly competitive race against myself,” she said. “I get bored easily, so curiosity and learning have been key.”
• Big-picture thinking. In any fast-paced industry, it can be difficult to consistently take the long view when it comes to making career choices. Things happen so fast that decisions easily become reactionary. Yvonne’s natural tendency to think things all the way through in a broader context helped her navigate the risk of always focusing on short-term rewards. Her advice: “Think about what gets you out of bed each day. But it’s also important to think about what you want to be doing two, five, or 10 years down the road. I’ve always optimized for the bigger-picture version.”
• Networking ability. “If there was one piece of advice I could give my younger self, it would be to start investing in my network earlier,” said Yvonne. She got intentional about her networking efforts in her late 30s and realized it’s something you should be doing as part of your job every day.

While these personal attributes set up Yvonne for success, she learned a lot along the way. Two lessons that stand out for her:

• Risks aren’t risky. Starting a new company, changing jobs, trying a new strategy—all of these things can feel like they put everything at risk. Yvonne felt that fear when she was leaving Accenture to go to VMware, but her executive coach helped her see that even if things didn’t go the way she expected, she’d still have options. The experience showed her that risks are rarely as risky as they seem.
• Asking for help is a sign of strength. No one knows every answer. But if we want to learn, we need to be brave enough to ask questions and ask for help. “It takes a lot of courage to get over the insecurity of vulnerability. I reinforce this with my team all the time: the smart people ask for help. That gets you down the field faster,” she said.

The democratizing role of open source

Yvonne is a big proponent of open source for multiple reasons. Puppet started with an amazing open-source project, and to this day Puppet’s open-source users are some of the most active and helpful folks. They engage enthusiastically, and they bring the company opportunities.

But open source isn’t a business model. You need to figure out how to create a long-term, scalable, monetizable model that enables you to benefit and give back without going out of business.

Related read: How MongoDB Scaled Their Open-Source Product with a Bottom-Up and Top-Down Sales Motion

This looks a little different for each organization, but for Puppet it’s a blend of open-source technologies with combined proprietary technology. And the glue that holds the strategy together is intense clarity around where Puppet focuses its commercial efforts (in their case, the Global 500).

“Open source deserves tremendous credit for the technological advancement that we have.”

But Yvonne’s love of open source goes far beyond her own company’s use of the strategy. “Open source deserves tremendous credit for the technological advancement that we have,” she explained. “It’s foundational to democratizing technology, making it easier for people to participate in development, which allows us to benefit from technology more quickly.”

She also pointed out how open source democratizes technology. It enables access, which encourages engagement from a diverse group of contributors all around the world—all different backgrounds, education levels, and ages. “Nobody’s judging you on how you look or how much money you have or where you got your education,” she said. “If you can bring value to the project, you will thrive.”

The power of purpose and the potential of diversity and inclusion

“I’m a huge believer in purpose, and I feel that everybody should have the opportunity to do things they find meaningful and important in their life,” said Yvonne. When she considers an opportunity, she thinks not only about the what, but also about the how.

For instance, when she was thinking about joining Puppet, she was attracted in part because she believes the work Puppet does is strategically important to the health and well being of many, many people around the globe. Then she dug a little deeper to look at how Puppet does what it does. She liked what she saw there, too, because Puppet places huge focus on diversity and inclusion and being engaged in the communities its people work and live in.

“That was really important to me,” Yvonne said. “Because I have a personal objective to demonstrate a different way of leading and engaging from a business standpoint—more around the elements of conscious capitalism that addresses all the different stakeholder groups—not just investors, but the communities and the climate, and all those other things.”

On the topic of diversity and inclusion, Yvonne thinks we can do better. She recommends developing a higher level of social consciousness about the issue around leadership tables. “We need to actively and aggressively diversify the top levels of leadership at the board, C-suite, and senior executive levels,” she said.

“We need to actively and aggressively diversify the top levels of leadership at the board, C-suite, and senior executive levels.”

She also recommends opening up how we think about sourcing talent. She wants to crack down on the idea that technology and software is a specific kind of path that’s only right for a very specific kind of person.

“We need to think outside of the box,” Yvonne said. “We have to approach the issue from the top down and from the bottom up and from the sides in. And we need to do it quickly.”

Related read: From Radical Candor To Just Work—Trier Bryant on Her Partnership With Kim Scott

The reason for her urgency is one we’ve all heard: The winning companies of the future will be the ones with diverse teams. Their diversity will give them the advantage of the best thinking and access to the best talent.

The best sources for insight into the future

What are Yvonne’s priorities for the next few years? As the mom of three teenagers, her biggest one is being a good mother and helping her kids go to college, and—hopefully—into careers they enjoy and love. Beyond that, she’s passionate about improving diversity and inclusion in the industry, and helping Puppet make its mark in the areas of infrastructure, automation, security, and compliance.

But Yvonne’s initial reaction when asked about the future was to quote William Gibson: “The future is already here.” To ensure she stays relevant in terms of where the world is now and where it’s going, she turns to the youth. In addition to having her own teenagers, she also sits on the board of Harvey Mudd, which is one of the leading STEM colleges. She works to understand what younger generations are looking at, how they like to engage, how their minds work, and what they value.

“The hard part isn’t envisioning the future, it’s figuring out the best path to get from where you are today to where you want to be tomorrow.”

She’s also intentional about spending time with entrepreneurs and people in the venture space because she values the way risk takers think differently. To help drive her own innovative thinking, she does an exercise that involves freeing the mind from all constraints of the real world in order to really imagine—if you didn’t have anything holding you back—what might be possible.

“We used to think the internet was just a great way to do e-commerce, but look at what we do with it now,” she said. “The hard part isn’t envisioning the future, it’s figuring out the best path to get from where you are today to where you want to be tomorrow.”

More from Yvonne

This is just a taste of everything Yvonne shared on BUILDing To Boss. Tune into the full episode below to hear more from her about how software buying has changed (and why), how to measure and quantify the customer experience, and how she balances all the different parts of her life.

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