Caught Being Good

Robert Chatwani, Tidemark Fellow

An uncommon career based on intuition, innovation, and integrity

What is Caught Being Good?

We built a Tidemark community of practitioners of excellence, but also people who we like, trust, and admire. Caught Being Good spotlights some of business’ best minds and their unique stories and brands of positive change. 

Who: Tidemark Fellow Robert Chatwani

What: President of Docusign, Former CMO of Atlassian, Former CMO of eBay North America

Why: Robert believes that purpose is a powerful filter, why is often more important than what, and the future will be forged at the intersection of technology, people, and potential.

Robert’s passion is building meaningful businesses that create hope and opportunity in the world, and doing it with high-performing teams. Whether helping the world’s entrepreneurs and producers connect directly to buyers at eBay or guiding the growth engine at Atlassian, he leads with both mind and heart. For Robert, technology isn’t just a tool to increase productivity or profits, it’s a way to build a tomorrow he deeply believes in, one that conquers humanity’s challenges by embracing the power of our individual and collective potential. 

Catching Robert doing good is easy – goodness is a baked-in trait and an ethos he furthers as a Tidemark Fellow. Here are 12 questions we asked Robert about his history, his vision, and what he’s excited about today. 

Q: Where did you grow up?

A: I grew up in the suburbs of Chicago. There’s a lot that I loved about growing up there, and I’ve built deep roots, which feels very Midwestern. Many of my friends and family still live there, so one of the things I love most is simply going back home to spend time with them. That, and picking up reminders to bring back to California. Whenever I’m back, I strategically plan my return to the airport with just enough time for me to stop by my favorite pizza place and pick up some frozen deep dish! Wherever I live, Chicago’s still home.

Q: What is your best childhood memory?

A: My favorite childhood memory is getting my first bicycle. During the summer, I’d often leave for the day without my parents knowing exactly where I was, but they knew I’d be back home in time for dinner. There was something magical and empowering about that sense of creativity  and exploration that my red and yellow Schwinn Stingray gave me – it was freedom on wheels! 

Q: How did childhood/young adulthood influence your professional path and career today?

A: There are three big things. First and foremost, my dad always taught me that there’s no substitute for hard work. My parents were immigrants from India who came to the United States in the early 1970s. After years of working for others, they eventually started retail businesses and became entrepreneurs. They worked incredibly hard, giving up what was comfortable to pursue their dreams and provide for our family. They taught me that success often comes with a tremendous amount of sacrifice. 

Second, I learned that the people you surround yourself with really matter. My father was fortunate to have individuals in his life that took him under their wings to coach and mentor him, and this helped him grow as a leader and entrepreneur. I observed first hand how powerful it is to have role models and to connect with those you can learn from, no matter your stage of life. My philosophy is to always be learning. 

There are a number of leaders I’ve had the privilege of learning from during my time at McKinsey, eBay, and of course Atlassian, and many of them are on what I call my “Personal Board of Directors”. They are my support team, and are always there to give me open, honest and unvarnished feedback on almost anything, professional or personal! One example is some advice that I received from John Donahoe, who is now at Nike but at the time was CEO of eBay. He said that there’s nothing more important than the alignment between your personal values and the purpose or values of the company for which you work. If that intersection is not strong, it’s impossible to thrive as a leader. 

Third and lastly: do your best to understand and be clear about what you believe in, and stick to it. Let the people around you know what you stand for, even if your views are unpopular. I saw my dad make decisions based on what he believed was the right thing to do, even when it was the harder path to take. He always asked himself: “Is this in the best interests of my family? Is this a lesson that I want my kids to learn from watching me?” I carry that with me to this day. 

Q: What was your “breakout” moment, professionally?

A: It was in 2004 and I had just joined eBay, which, at the time, was experiencing hyper-growth. Prior to eBay, I was an entrepreneur, having started an online barter marketplace called MonkeyBin. I was probably six to eight months into my job at eBay, sitting in a cubicle in San Jose, when I realized that I was witnessing the birth of online commerce at scale. It was sort of the start of a true global economic democracy. 

It dawned on me that this model of trade – buying and selling between people who had no prior connection yet were bound by trust – had not yet achieved its potential in terms of reach. I thought, “Wait a second. I’m part of a business that’s the world’s most powerful engine for commerce, yet it isn’t accessible by those living in parts of the world that could benefit the most. How can we fix that?”

That spawned an idea: What if you could take the world’s producers and artisans, and connect them to a global marketplace? What would be possible? At the time, our CEO, CFO, and President all rallied around the vision. Jump forward, and we forged a partnership with the private sector arm of the World Bank to build the world’s largest sustainable commerce shopping experience within the broader eBay Marketplace. That led to us building and scaling a number of new ventures across eBay and PayPal, including eBay for Charity, which has raised over $1 billion for charities throughout the world. We had a positive impact on tens of thousands of global entrepreneurs and organizations through these programs. It helped that the leadership team at eBay, including our founder, Pierre Omidyar, believed that the business was a force for good. eBay is the place I learned to take an idea – any idea – and always dream one size bigger. 

Q: Tell us about a moment when something you really cared about went wrong. How did you manage that?

A: During my 12 years at eBay, I inevitably had to make some tough decisions. There was a moment during that journey when the company made a decision to let go of about 7% of the workforce. For better or worse, there’s a pretty standard playbook, along with legal requirements and paperwork, that goes along with a process like this. The easiest thing to do would have been to execute on the playbook. However, being part of a very purpose-driven company, I felt empowered to do this my own way. I pushed back and asked questions like: What’s the environment in which we’re communicating this? What’s the message we’re delivering? What help are we going to provide? How much time are we giving people?

None of those things alone made a big difference, but pausing to ask these questions and handling this the right way – in a human way – really mattered to me. I’m a big believer that how you do something often matters just as much as what you’re doing. I asked myself how I would want to be treated in a situation like this. It led to a leadership discussion on empathy, because being human matters. It’s about that person-to-person connection, especially when you’re having hard conversations or have to make tough calls. It didn’t change what we needed to do, but it dramatically shifted how we did it. 

In my view there are two really important moments when you’re part of an organization. The day you join, and the day you leave. The memories always stay with you, and these moments really matter. 

Q: Where do you see the most potential for good in your work and career?

A: The through-line of my career journey is organizations – either those that I’m building or those that I’m contributing to – that are at the intersection of technology, people, and opportunity. At eBay, it was about commerce, community, and creating access for global sellers and entrepreneurs. At Atlassian, it’s unleashing the potential of teams through better and smarter ways of working. 

In Silicon Valley, we often get so focused on the tech itself that it’s easy to lose sight of what it is in service of. I’m a big believer that technology should be in service of advancing humanity and improving life – be it our personal lives, our work lives, or the communities we live in. It may mean creating economic opportunity, helping individuals and teams reach their potential, alleviating suffering and improving longevity, or creating a more sustainable and just world. Any number of human and societal challenges can be improved and supported through the use of technology, as long as we are clear who we are trying to serve and why we’re doing it. That’s the starting point for any worthwhile endeavor.

Q: Who is your hero?

A: I have two. First, my father, because he taught me about the power of resilience and perseverance. He passed away about 10 years ago, but not a day goes by when I don’t think about a lesson that either he taught me or that I learned by observing him. 

Second, I have admiration for Mahatma Gandhi and his belief in being the change you seek in the world. We all have the power within us to serve humanity in some way. “Be the Change You Seek” also happens to be one of Atlassian’s company values. Every big idea starts with a small change and a small action; there’s a huge amount of power and potential in that. 

Q: Tidemark has a saying, “You can’t pour an empty cup.” How do you fill your cup?

A: For me it’s about living and being on purpose. Many years ago, inspired by my coach Vance Caesar, I took out a piece of paper and wrote down my purpose: why I do what I do. And for me, that hasn’t changed. I love building meaningful businesses with high performing teams that create hope and opportunity in the world. And, I strive to serve as a role model for my family – as a great husband, father, and son. That’s it. I work hard to align decisions I make about how I spend my time, who I spend my time with, and what I work on, with my “why”. When things feel aligned, it creates a lot of energy for me. I keep my cup full by constantly using my purpose as a filter to focus my time and my energy.

Q: What would the title of your memoir be?

A: Life Discovered, Not Planned.

Q: In five words or less, what does the world need?

A: More love, less fear.

Q: What are you excited about, right at this moment?

A: Human potential. At Atlassian, we get the privilege of working with hundreds of thousands of customers across many industries: life sciences, automotive, biotech, e-commerce, financial services, and more. We get a bird's eye view into how teams around the world are moving work forward. I believe we’re in a digital renaissance of knowledge work, where the rules of how and where we work and collaborate are being completely rewritten. What we observe is that the pace and amount of innovation that is taking place – for breakthroughs that haven’t even been launched out into the world yet – is mind-blowing. It gives me unbounded optimism for where humanity and the world is going.

Q: What do you want to be your legacy?

A: That’s a big question! In relative terms, none of us are here for very long, and that’s an important reminder. For the time I am here, I want to demonstrate how anyone can be a role model for someone else – as a leader, a parent, or simply as a friend. Through my actions and decisions, I want to show how acts of leadership, kindness, and generosity can inspire others to be the best version of themself. I don’t believe in allowing fear and scarcity to define our life decisions. To me, there’s nothing more powerful than leading a life defined by love, abundance, and serving others.


May 2022

The information presented in this post is for illustrative purposes only and is not an offer to sell or the solicitation of an offer to purchase an interest in any private fund managed or sponsored by Tidemark or any of the securities of any company discussed. Tidemark portfolio companies identified above are not necessarily representative of all Tidemark investments, and no assumption should be made that the investments identified were or will be profitable. For additional important disclaimers regarding this post, please see “ Purpose of the Site; Not Investment Advice; No Recommendations” and “Regulatory Disclosures” in the Terms of Use for Tidemark’s website, available at Terms of Use (

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