Yvonne Wassenaar of Puppet

    We Spoke to Yvonne Wassenaar of Puppet on How to Rebuild in the Post COVID Economy

    As part of my series about the “How Business Leaders Plan To Rebuild In The Post COVID Economy,” I had the pleasure of interviewing Yvonne Wassenaar.

    Yvonne Wassenaar is the CEO of Puppet, a trusted enterprise provider of IT automation software across traditional and cloud-native environments. She has more than 25 years of experience scaling companies globally and driving enterprise transformation with technology. Prior to Puppet, Yvonne served as CEO of Airware, CIO at New Relic, and held multiple leadership roles at VMware and Accenture. She is currently a board member of Forrester (FORR), Anaplan, and Harvey Mudd College. Amidst growing concerns with how modern technology could be used, Yvonne is championing it to drive a safer, more efficient and innovative planet.

    Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

    I started as a COBOL software engineer, back when COBOL was cool the first time around, but was disenchanted by the waterfall approach to software development and wanted to get closer to the business. Post business school, I moved into strategy consulting and while different from engineering, in many ways shares the same logic and art of programming and focused my efforts in the technology sector. In total, I spent 17 amazing years at Accenture going from software engineering to strategy Partner.

    As I looked to diversify my own experience, I jumped from consulting to an operating executive role at VMWare. I held several executive positions and ultimately worked for Pat Gelsinger, the CEO, as we focused on positioning VMware for its next big chapter of growth.

    It was at New Relic where I was able to then apply my many learnings as we took the company public and post-IPO, I became the New Relic’s first-ever CIO. In parallel with this, I joined my first non-profit boards (Harvey Mudd College & The Athena Alliance) and also a private company board (Bitium) and public company board (Forrester). From there I joined Airware, a drone analytics company, as COO and ultimately CEO and joined Mulesoft’s board before the company sold to Salesforce.

    All of these experiences formed the foundation for me to take on my current role as CEO of Puppet and enabled me to join the board of Anaplan.

    Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

    Turning back the clock to 1992, this story is perhaps more painful than funny, but very foundational and one I often reflect on. I had just been promoted to manager at Accenture back when I was still writing code. We were on a very intense project that was behind schedule which translated into a lot of very late nights. Of all the bad luck, the coder they put on my team at the time, the first person I ever needed to manage in my career, was HORRIBLE. I could not believe he had not been fired. He could not debug his code for the life of him. I would end up standing over his shoulder until the late-night hours thinking to myself I should just be doing this myself (and sometimes I did). In retrospect, I am surprised this poor gentleman didn’t quit on me. How stressful to have someone back-seat coding over your shoulder. Thankfully some good mentors help me recognize that my job as a manager was not to stress people out or make people feel bad. It was my job to create an environment where people could do their best work and to give them tips and skills to do their jobs better. The reality was that I was the one being horrible at my job back on that first project, not the coder. I often think back these early days when I am struggling with someone on my team — is it them or is it me? Are there things I can be doing better to support this individual’s success and sense of accomplishment in their work?

    Is there a particular book that you read, or podcast you listened to, that really helped you in your career? Can you explain?

    One of the great benefits of working at a large enterprise like Accenture is the investment they make in your career from an early age. For me, one of those transformative investments was a course that introduced me to the work of Stephen Covey and his book The 7 Habits of Highly Effective People. As an “action-oriented” person, I found it is easy to get sucked into the momentum of checking things off of my to-do list 24 x 7. I found this concept of segmenting my to-do list into a two by two matrix where important/not unimportant is on the vertical axis and urgent/non-urgent is on the horizontal axis powerful. It opened my eyes to how many things I was spending my time on that probably did not deserve any time at all, as well as how many important but not urgent things I was not spending enough time. Over twenty years later, I still leverage this framework to prioritize where I spent my time on both the work and family front. For example, without conscious effort, it is easy to be too busy to see what silly creation the kids have cooked up, sit down and watch a comedy show on the couch or make a nice breakfast for the family. While these are not urgent, they are important. Kids grow up quickly and it is important to make sure they don’t grow up without you, no matter how important you feel your work might be.

    Extensive research suggests that “purpose driven business” are more successful in many areas. When you started your company what was your vision, your purpose?

    When I was 36 years old, my fiance was diagnosed as terminally ill with cancer. Home with the help of the hospice service, he woke up one night at 3am and could not fall back asleep. We ended up getting some tea as he reflected back on his life and expressed regret that he had not done more with it. He felt he had failed to take the risks and do the things that really mattered; that he had failed to follow his true dreams. It was devastating to hear and I committed to myself at that time that I would make every day I had left on this planet matter. I thought deeply about this when I decided to take on my current role at Puppet. I even challenged my team the day I started to reflect on the purpose of the company, the vision I had for what we could do together, their role in that vision. I encouraged the team to ensure that they felt the same sense of purpose that I had for the company and if they didn’t that it was okay; they should seek that sense of fulfillment and purpose elsewhere and I would be supportive of that change.

    Puppet eliminates the soul-crushing work associated with managing and scaling out technology infrastructure. As software starts running more and more of the world around us, Puppet enables us to have a safer, more innovative and more equitable world. But it is not only what Puppet does that I believe is meaningful, it is how we do our work that has purpose.

    We are big believers in the power of open source and how by open-sourcing technologies, you can democratize the access and advancement of that technology. To this end, not only do we continue to head a powerful portfolio of open source projects ourselves, but we also encourage our teams to contribute to other open-source projects and as a company have started contributing to upstream projects. Open-sourcing goes beyond just technology, we are also going to be open-sourcing our playbook to re-opening our offices so that we can learn and grow together in a safe and scalable way.

    We also believe that companies can fuel innovation and competitive advantage by drawing on diverse backgrounds, skill sets, and perspectives. Throughout my experience, I’ve found that diverse teams are more effective in solving problems and delivering stronger results. But more than just hiring diverse candidates, companies must foster an inclusive environment. For example, we recently introduced our IDEA council, a collective of perspectives and voices from around the globe who aim to make a positive impact. This group helps oversee and assess the effectiveness of our inclusion, diversity, equity and access (IDEA) efforts, introduce reform and/or innovation when needed, and help drive organizational change in partnership with our People team and executive leadership. Given the importance of diversity in positions of power when you are working to move the needle on change, I have diversified my board (now composed of 3 women and 4 men) and expanded the diversity of my executive team. Only collectively can we make the needed difference around the world.

    Do you have a “number one principle” that guides you through the ups and downs of running a business?

    My number one principle that guides me through the ups and downs of running a business is to make hard decisions and make them with integrity, honesty and social consciousness. All too often people shy away from hard decisions to the detriment of those around them. They fail to consider the societal and environmental implications of their decisions (or indecision which is a decision itself), they fail to give hard feedback, they fail to exit a part of the business that has suboptimal performance and a bleak future. What I remind myself, however, is that making hard decisions should not be reserved for when a crisis hits, but it should be part of how we assess every day. We need to take the time to ask the hard questions, look at the short and long term implications of making (or not making) key changes and have the courage to do what is right. Importantly, this means you should be transparent with your teams on the journey you are on and the decision processes you use. You should also go the extra mile to make sure that when a decision negatively impacts people, those people are treated with care, empathy and respect. Only by doing this can you, your team members, and your business reach their truest level of impact in the world around us.

    Thank you for all that. The Covid-19 pandemic has affected nearly every aspect of our lives today. For the benefit of empowering our readers, can you share with our readers a few of the personal and family related challenges you faced during this crisis? Can you share what you’ve done to address those challenges?

    I’ve found that one of the biggest stressors throughout this situation has been the unknown; not knowing when my kids might go back to school, not knowing when I’ll see my colleagues again in person, not knowing how the virus will personally impact my loved ones.

    I’ve found that one way I’m able to bring order to all these unknowns is through scenario planning. At Puppet, we’ve used scenario planning to help us get our arms around what different potential futures might mean to our business strategy and workforce, but I’ve also done a bit of scenario planning in my personal life. I’ve started mapping out what my life will look like in the fall given I have 3 school-age kids (a 14-year-old in high school and 12-year-old twins in middle school). So, I’m thinking through my plans for each potential situation: whether my kids go back to school full time, if they go back part-time, or if they stay home and continue learning in a distance format. This helps identify no regret moves I can make today that benefit us going forward in all of those scenarios and develop a playbook for the nuances of each as well. By doing this, I’m able to get the upper hand on those stressful unknowns in my life.

    Can you share a few of the biggest work related challenges you are facing during this pandemic? Can you share what you’ve done to address those challenges?

    Puppet is fortunate in the sense that we are a software company and it is very possible for us to operate remotely. That said, during normal times, ~70% of our team works out of one of our five global offices and the rest of us typically are flying around and engaging with customers, partners and our community fairly frequently. This meant that while we were technically able to move to an all-remote company, it is very hard on us as team members, family members, leaders and individuals. This is particularly true given the complicating challenges of the “shelter in place” orders and the closing of schools (requiring many team members to need to manage the homeschooling of their children as well — myself included). Stress and anxiety can arise from everything from a feeling of extreme isolation for some of our team to being completely overwhelmed for others. There are a variety of ways we have been working with our team to deal with these challenges including:

    • A lot of video conferencing. This helps us stay connected and the team has gotten creative to keep the personal connections going through virtual happy hours, trivia games, scavenger hunts, virtual talent shows and more.
    • Since many people did not have home offices before the work from home orders came into play, we are letting people check out furniture from offices to help improve their home work environment where it is safe for them to do so. We have also set up a special expense budget so they can purchase needed items as well.
    • We are also actively working on the plans to get people back into the office (in a socially distanced way) for those team members looking to get back into the shared physical work spaces. The key to planning this is ensuring we are being thoughtful of both employee and community safety and that we are being guided by data versus dates. Engaging the team in this work and open-sourcing our playbook as it is developed is a key way we are empowering our team during a time when there is so much stress related to the unknown.
    • And while all of these things have been helpful, we have still found our teams are very understandably more stressed than usual. In fact, for some of us, the stress and anxiety is like a migraine — it is so ever-present you can forget what it feels like to not have one. To help address this challenge for our team at Puppet, we declared Monday, May 4th, Star Wars Day, a holiday for 2020. We did this so people could focus on high-priority items outside of work and what was most striking was how so many people commented on how much they needed that break and didn’t even realize it. This was so well received we recently declared Monday, July 6th another company holiday in 2020 and we are encouraging people to take PTO during this time as well. Even for those sheltering in place, taking PTO during this time can help reset and redraw that line between professional and personal lives, which has been increasingly blurred.

    Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the coronavirus pandemic have understandably heightened a sense of uncertainty, fear, and loneliness. What are a few ideas that you have used to offer support to your family and loved ones who were feeling anxious? Can you explain?

    These are particularly challenging times for everyone, though the challenges are different based on your personal circumstances, and during this shelter in place era, based on your home living conditions.

    For my immediate family of five people (two adults and three children the ages of 14, 12, and 12) we are fortunate to all be healthy and to get along well and enjoy each other’s company. At the same time, like so many others, there is a heightened sense of stress and anxiety in the household. For my children, the hardest part is missing out on the social aspects of being a kid, of playing with friends, missing out on baseball season, and not being able to just get out and about. Additionally, my kids are old enough to hear the news and read the blogs that can be grim as the deaths from the virus continue to climb and uncertainty abounds. To help us manage our stress and anxiety:

    • We are all focusing on the basics of mental health including keeping routines, eating well, getting exercise and getting enough sleep.
    • What has been particularly nice, and helpful, is that we have also found extra enjoyment and relief in the “family dinner.” It is the most anticipated time of day in the house. While we have always tried to do the family dinner at the table to chat about the day’s events; these days we tend to stay longer and longer as the pandemic progresses to check-in, laugh, engage and debate what is going on around the world.
    • Reconnecting with nature is another welcome and refreshing way to recharge. So, in addition to the regular routines associated with taking care of our pets (including 3 bunny rabbits, 4 chickens, a cat and a dog), we have started up a home garden with spinach, strawberries, tomatoes and lettuce. These activities, along with daily walks around the neighborhood park, are not only helping us manage through these times but also bringing us closer together as a family — one of the many silver linings of COVID-19.
    • We also talk about what it all means and the potentially positive short and long term outcomes of the pandemic so that my children understand the power they have to guide us towards a better world. While it is undeniable that there is a lot of tragedy and pain in the world right now and the uncertainty is stressful, we are also seeing many good things happening as well. In some regards, the world was running too fast and this has forced us to pause; to reconnect as communities and families. We have been able to accelerate many powerful trends such as telehealth, virtual learning, greenhouse gas management and the like. We are realizing that we probably don’t need to travel as much as we all have been doing and while we desire to get away from 100% virtual engagement, some of it is really powerful and engaging.

    Obviously we can’t know for certain what the Post-Covid economy will look like. But we can of course try our best to be prepared. We can reasonably assume that the Post-Covid economy will be a trying time for many people across the globe. Yet at the same time the Post-Covid growth can be a time of opportunity. Can you share a few of the opportunities that you anticipate in the Post-Covid economy?

    Puppet’s technology runs some of the most critical businesses, governments and municipalities around the globe and the current situation highlights the opportunity we have to help leaders run their organizations more efficiently, securely, and remotely as they navigate the crisis to a brighter future.

    As companies emerge from the crisis, we expect a “new normal” to have arisen that aligns well to the portfolio of offerings Puppet brings to our community and our customers:

    • Remote work is here to stay: Initially, businesses have had to find more ways to work remotely. Post COVID-19 they will recognize that being able to work remotely is not only a good business continuity capability for the company, but also something businesses will need to offer in order to attract and maintain the best talent as employees discover the value remote work.
    • Innovation will be key to winning. The pandemic is separating out the future winners from losers. Companies who spend all their time keeping the lights on during the crisis will emerge outdated and unable to adjust to the new demands of customers. Companies who work to drive efficiencies and cost containment during the pandemic without turning their back on innovation (in our world, companies that continue to automate their infrastructure and take advantage of technologies such as K8S and cloud-native) will win.
    • Security and compliance will be “must-haves.” With more workers accessing company operations remotely, it is essential to ensure the networks are secure and systems are protected against exploits and vulnerabilities. Similarly, compliance will also play a larger role in business software moving forward. Companies that can incorporate continuous compliance policies into their technology infrastructure will save thousands of dollars and countless hours by reducing the complexities of audits.

    In practical terms, from an IT Operations perspective, how leaders adjust to this “new normal” will vary. Some may accelerate their infrastructure automation projects from managing hundreds of nodes to hundreds of thousands of nodes to better support remote work and business continuity. For others, it may mean tighter integrations with Splunk, ServiceNow and other security tools as companies streamline security operations by closing the “find it, fix it” loop over expanded attack surfaces. For some, it will mean taking that first step towards infrastructure automation that perhaps just wasn’t a top priority in the past. Whatever their needs are, Puppet is here to help our customers operate and scale their infrastructure in secure and compliant ways by leveraging our portfolio of automation offerings, including Puppet Enterprise.

    How do you think the COVID pandemic might permanently change the way we behave, act or live?

    The pandemic has significantly caused us to change how we behave, act, and live. Given the duration of these changes, people are being forced to break down old beliefs and try new things; some things they will discover they really like and will be lasting changes over the years to come; many of these changes will be the acceleration of trends already in the works including:

    • Much of our personal lives will be virtually enhanced. People are realizing that leveraging video conferencing to connect with people can be a great way to stay in touch with loved ones who live far away and/or can not travel and I doubt the virtual dinner parties will entirely go away. Selecting a new pair of glasses by trying them on virtually before ordering them or swinging by the physical store to pick them up is another example of a technology here to stay. In general, online shopping is more convenient than many of us realized.
    • More and more work will be done remotely. While challenging for many initially, people are starting to experience the benefits of remote work and companies are being forced to get used to it as well. My prediction is we will start to see more people taking advantage of working from home to enable more balance in their lives; particularly when commute times to an office are long and/or family members at home need care. Additionally, we will likely see more people moving to different areas of the country, maybe to be closer to family or to escape the expensive rent. All of these trends have the potential to support more diversity in the workplace and fewer emissions of greenhouse gases if effectively implemented.
    • More focus on physical and mental health. It is clear that we are living in highly stressed times and more companies and individuals are talking about both physical and mental health. There is an opportunity for us to continue this heightened sense of awareness and care of both physical and mental health as we exit the pandemic.
    • More telemedicine and distance learning. We are also all getting used to having our health care and educational needs being met virtually. While I don’t see many people keeping to a 100% virtual approach to either health or education, it is clear that there is an opportunity for an increased hybrid approach to both which can increase access, lower costs, and enable new and exciting innovations that are good for individuals and corporations/institutions.

    All of these changes ideally enable us to be more community conscious, more socially connected, healthier, and to do more (traveling less) in support of a healthier Mother Earth as well.

    Considering the potential challenges and opportunities in the Post-Covid economy, what do you personally plan to do to rebuild and grow your business or organization in the Post-Covid Economy?

    While the onset of COVID-19 has been very disruptive to our teams, the communities they live in and the world around us, both economically and health-wise, I do see some great opportunities for Puppet to emerge an even stronger and more impactful player going forward.

    • From a people standpoint, we are committed to nurturing a growing remote-hybrid model of operations. We understand the benefits remote work provides our employees and we are excited about how this flexibility can help us create more inclusive and diverse environments. At the same time, we understand the important role our offices play in providing cultural gathering spots and enablement for our team, our communities, and our customers. We will continue to nurture and leverage our offices in these powerful ways while ensuring ongoing flexibility for our teams.
    • From an operations standpoint, I am increasing our focus on investments that deliver efficiency and optimize the business while increasing our customer intimacy. This has involved streamlining our organization to increase agility, including kicking off a cross-team effort to drive increased customer engagement and doubling down on our OKR process as our alignment mechanism within the company.
    • From an offerings/investment standpoint, we have refined our offering portfolio and investments to align with the “new normal” we see arising. This means we are squarely focused on extending and enhancing the lives of current investments our customers have without turning their backs on innovation. These investments include the simplification and scale-out of our Puppet Enterprise platform and the launch of new cloud-native, task management, patch management, and compliance solutions.

    Similarly, what would you encourage others to do?

    Every business should take this time to rethink its purpose, its operating model, and its talent strategy. There are great opportunities to use this pandemic as an accelerant of positive and powerful change. As you do this, ensure you are not completely turning your back on innovation in an effort to achieve needed cost savings and efficiency. While cost savings and efficiency might save you short term, exclusively focusing on these may well limit your long term viability. Opportunities you may want to consider to get the best of both worlds are in increasing the automation of your business processes and infrastructure as well as leveraging machine learning in what you do. From a talent perspective, think through and start investing in your long term strategy now; build out new opportunities for ongoing remote work as a way to enable greater flexibility along with finding new ways to skill up, grow and engage your team.

    Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

    “Be the change that you wish to see in the world.” This quote, which is often attributed to Mahatma Gandhi, is one of my favorite “life lesson” quotes. What I find so powerful is its simplicity and power. It asks us to stop judging others, replace complaining and a victim mentality with self-reflection and an empowerment mentality, and it encourages us to take action through our own being. For me, a particular area I practice and preach this mentality is around diversity, inclusion, access and equity in technology and leadership. Having worked in this industry for almost 30 years I have been witness to and heard many horrible stories. What I started to recognize, however, is that being frustrated or angry was not going to really change anything. I realized that to change things, I needed to become the empowered female leader I did not see enough of in the world around me; that I needed to be the leader who created a diverse and inclusive environment for my team; and that if I could be these things that I wanted to see in the world, that others would do the same and collectively the world would be truly different as well.

    How can our readers further follow your work?

    Be sure to check out all the cool things we are doing at — and you can follow me on LinkedIn and on Twitter at @ytechdata.