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Puppet CEO Yvonne Wassenaar, left, visits a pumpkin patch with her family. (Photo courtesy of Yvonne Wassenaar)

Not only has Yvonne Wassenaar worked in Silicon Valley and the San Francisco Bay area most of her career, it’s also where she grew up.

But recently, she got a new perspective. Almost a year ago, Wassenaar took over as CEO of Puppet, a Portland-based, 500-employee cloud automation company that helps customers develop software. The 14-year-old business has raised $150 million from investors over the years.

So how does the city embodied by the chill, hipster vibe of “Portlandia” stack up against the win-at-all-costs depictions of Silicon Valley?

Wassenaar sees pros and cons to both.

“Because of the economics in [Portland], you can attract people who want to have it all,” she said. Housing, restaurants and recreation are all cheaper, while still offering good jobs in the tech sector.

In Silicon Valley, competition permeates the culture.

“It becomes more about, ‘How am I doing relative to other players?'” she said. In Portland, “it’s more about, ‘How am I driving impact?”

And the downsides to the City of Roses?

In Portland, “there is just not as much depth and breadth of startup experience,” Wassenaar said. That’s a shortcoming in the collective knowledge base.

“You learn a lot,” she said, “from what doesn’t work and from trial and error.”

Yvonne Wassenaar presenting at an event hosted by Zuora. (Photo courtesy of Wassenaar)

But Wassenaar does see more venture capital and startup talent defecting from California and spreading to the Northwest and elsewhere.

In her role, Wassenaar is eager to expand Puppet’s customer base to bigger companies, moving beyond “super users” of their tools. She wants to shift from talking about solutions for solving specific use cases, to putting their products into a business context. Wassenaar wants to be a leader in a “container-based world.”

“We’re in just an incredible spot really to not just support, but to lead the companies we work with,” Wassenaar said.

Her scaling strategy is to broadly apply the agile software development philosophy to expanding Puppet’s products. Wassenaar is a fan of going through fast iterations and continually learning by doing small experiments and making small refinements.

Some of that thinking comes from the Valley, she said, which is tuned into resilience and the idea that you can “fail responsibly, creating an environment where you can make mistakes and get to the right outcome faster.”

As the rare female CEO — just 5 percent of Fortune 500 CEOs, for example, are women — Wassenaar is eager to help other leaders diversify their corporate boards and employees. Many male colleagues are asking for her help and perspective as they diversify their teams. She emphasizes that inclusion — making people feel heard and valued once part of a company — is just as important as hiring them in the first place. She agrees that it’s key that there are diverse perspectives represented in tech development.

“Diversity and inclusion is one of the most important business topics on the agenda today,” she said, “and the reason for that is technology is changing every aspect of life around us.”

We caught up with Wassenaar for this Working Geek, a regular GeekWire feature. Continue reading for her answers to our questionnaire.

Current location: My family lives in San Francisco, not far from where I grew up in Saratoga/Sunnyvale (the current day Silicon Valley), though Puppet is headquartered in Portland with offices and customers around the globe, so I find myself spending a fair amount of time at airports and on the road.

Computer types: I use a MacBook Pro (recently upgraded because of the amount of video conferencing I do with people in an increasingly connected world and the need for a bit more oomph). This is a touch controversial as my partner (and tech support on the homefront) is deeply “anti-Apple” and while he runs the home server and firewalls, he refuses to use a Mac because it doesn’t have a touch screen. Well, this year the three kids have all been asking for Macs because that is what is cool in school. Let’s see where the homefront lands in a couple years.

Mobile devices: I was a long time fan of the Blackberry because I loved the feeling of those little keys under my fingers. Ultimately, however, the apps on the Apple phone ultimately stole my heart (and dramatically improved my productivity). My current phone is the iPhone X, which doubles as my camera. My biggest disappointment is the never ending changes in power cords and the inability to charge my phone and use my headset (unless I am using my Airpods, which I bought for that reason and are fabulous to go running with, getting rid of the never-ending wire management problem).

Favorite apps, cloud services and software tools: I’m all about apps that drive efficiency and foster connection. As a mother of three who travels a fair bit, I love Amazon because it saves me a lot of time as I run the household and Puppet. I also use Waze, Lyft and Routsey because they help me get around efficiently. Despite the fact the technology does not yet work seamlessly, I’m a big fan of video conferencing (BlueJeans, FaceTime, and Zoom) because it enables me to create better connections across our global customer and employee base in a more personal manner without needing to always be in person. And in an increasingly collaborative world, I find it very valuable to be able to work with others on documents and presentations through Google Docs and Google Slides.

Yvonne Wassenaar still lives in the San Francisco Bay area and commutes regularly to her Portland office at Puppet. (Puppet Photo)

Describe your workspace. Why does it work for you? Being a road warrior of sorts, my location is ever changing so my workplace is best defined by my computer, phone and me. You can find me working on an airplane, in meeting rooms or seated in one of our many open spaces in the office. For some people this type of lifestyle would drive them crazy, but for me, I love the variety.

Your best advice for managing everyday work and life? It’s important to set your own definition of what “doing it all” means based on your own life priorities. Don’t judge your success day-by-day but rather week-by-week so you can more creatively manage what matters most.

For me, the biggest challenge is ensuring I am spending enough quality time with my family and finding time to take care of my physical and mental health. One technique that works well for me is to keep a calendar where I track how many days I am sitting down and enjoying dinner with my family and how many days I go for a run or to yoga. I set an average target number for each of these activities and then measure my success on a weekly and monthly basis. This has enabled me to determine at work what I need to say no to or when I need to rebalance my workload to get my life balance in check.

Your preferred social network? How do you use it for business/work? LinkedIn. It enables me to stay connected with a network I have built over decades, especially as people change jobs more frequently today than they did in the past. LinkedIn keeps me up-to-date on interesting developments such as job changes, work anniversaries, and posts by colleagues that I otherwise might miss. Additionally LinkedIn enables me to get quick context on the people I am recruiting or looking to engage with, and it provides me a platform to get my own perspectives out across my network.

Current number of unanswered emails in your inbox? Too many to count. According to my phone it is 41,700. Why so many? The spam filters don’t catch all the spam. I have a variety of newsletters I subscribe to. I am on school and sports mailing lists and I get cc’d on emails that I don’t really need to read and respond to, combined with it takes too much effort to delete things I am not interested in and I have not set up great filtering rules (yet).

What do I read? Depending on time pressure, I do value my news summaries. Time sensitive family items pop to the top along with requests for input from my team, customers and stakeholders. The advice I give to my team is to not take an unresponded email request as a sign that I don’t want to do something. If you don’t hear back, try again. Likely the first request got lost in the pile of other unread emails.

Number of appointments/meetings on your calendar this week? A lot. Roughly 30 a week or about six meetings a day during the week. The reason for so meetings/events is driven by the fact that I am a very hands-on leader. I deeply value connecting with as many members of the Puppet community as I can to understand what is really going on and how to drive accelerated impact. It is also important that I am strengthening and building our external network, ensuring we thoughtfully understand our customers’ pain points and opportunities. Being a global company, my meetings can start as early as 5 or 6 a.m. and extend into an evening event. When do I have “thinking time?” Typically in the very early morning hours, on a long run, or when I am commuting on the train, a plane or in my car.

Yvonne Wassenaar at a family graduation event. (Photo courtesy of Wassenaar)

How do you run meetings? I believe meetings work best when they have a clear purpose and adhered-to rules of engagement. I work to ensure we have alignment on the agenda and objectives in advance, send out pre-reads where relevant, look to engage in dialogue and discussion (versus just doing updates), and recap agreements and action items before we leave.

I keep meetings small though sometimes end up being guilty of having 10 or more people in the room, which is not a great practice if you are really trying to work through challenges and opportunities. Typically in these situations you end up with five people in a meeting and more than five people observing from inside the room. If things start to spiral or go poorly in a meeting, I leverage tools such as parking lots and “hitting pause” to move to another topic. Ultimately, I am thankful that my 17 years in consulting gave me a lot of practice on meeting facilitation that serves me well today.

Everyday work uniform? It varies depending on my location and what’s happening in the day. It could be anything from jeans to a dress with “fun” shoes or occasionally barefoot, if I don’t need to leave my house or hotel room.

How do you make time for family? It is probably the hardest and yet most important thing that I try to get right every week. What seems to work best for me is to get up early to work before the household gets up, block important kid events on the calendar and treat them as my most important meetings of the week. I work hard to have family dinner time together where we can all catch up at least four times a week or more. I also always have a family trip or two on the calendar to look forward to.

Best stress reliever? How do you unplug? I find the best stress relief in doing physical activity. I love taking my 75-pound dog Max for a run in Golden Gate park or riding my bike down to the yoga studio for some hot yoga. Music also plays a big role in my life, allowing me to escape into a different mind and emotional space.

Wassenaar takes a break from the world of cloud computing to play in the snow in Tahoe. (Photo courtesy of Wassenaar)

What are you listening to? Top pop or country music is what I listen to most often these days given that I live with three “almost” teenagers. Depending on my mood, occasionally I go back to the classics from the 1970s and ’80s. There are also times I enjoy classical music (Mozart was my Dad’s favorite along with Beethoven and Handel) and then there are the beautiful sounds of George Winston on the piano or Yo-Yo Ma on the cello.

Daily reads? Favorite sites and newsletters? I wish I had more time to read and yet time is scarce. Given this, I do value the newsletters that help to quickly separate the signal from the noise. My regular reads are GeekWire, CEO Daily, The Broadsheet, PitchBook News and the Economist.

Book on your nightstand (or e-reader)? “The Lightning Thief” by Rick Riordan. Probably not the most common book for a CEO to be reading but a fun one that blends Greek mythology and adventurous kids (somewhat along the lines of Harry Potter). The back story on how this ended up on my nightstand? A friend of mine is a Broadway producer, and he recently did a fabulous and engaging musical interpretation of the book that drew me into it. It allows me to take a break and free my mind from the more technical and business issues that consume my daytime hours and reminds me of the values and moral challenges that we can face as we live our daily lives.

Night owl or early riser? I try to get work done before my kids are up, so I benefit from being an early riser. However, I also love to nap when I have the luxury. Helping my napping habit is the fact that I can sleep almost anywhere (especially on airplanes). Key to a good nap: eye shades and ear plugs. I have built up a good collection of eye shades from many an international trip in United business class over the years.

Where do you get your best ideas? Best ideas is a subjective assessment. That said, I believe I get my best ideas when I am going for a run, doing yoga and, on occasion, when I bounce crazy ideas off of colleagues in situations where we really let ourselves push outside the box. What enables us to think out of the box? Taking away constraints (fear is not a great advisor) and pushing people to define really crazy ideas (ideas that clearly may not be feasible) to create space to see options and opportunities that represent step change versus incremental shifts.

Whose work style would you want to learn more about or emulate? PagerDuty CEO Jennifer Tejada. She has done a fabulous job with PagerDuty (a San Francisco-based cloud computing company), driving purpose, profit and diversity in an integrated and powerful way. I work to incorporate this into my own leadership style by surrounding myself with sponsors, mentors and team members who share the same core values. I engage regularly with Jennifer and others whom I respect to push my thinking and my prioritization of focus areas to ensure I am leading with integrity, purpose and power.

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