Four Women

In celebration of International Women's Day, I'd like to repurpose some content that I wrote on Medium five years ago. Feel free to read the piece which has added context and numbers showing the challenges that women and underrepresented groups face in careers in technology and becoming founders. I did want to repost about specific women who have had a huge influence in my career. They, along with my wife Sarah, have been so influential in shaping who I am, how I think about problems, how I interact with all sort of people and so much more. Any success I have had is thanks in a large part to their help, guidance, hard work, attention to detail, ability to think big, and overall support. To these women and all the women who I have had the opportunity to learn from and work with, I am so grateful.

1 | Mary-Lou

Mary-Lou is hands-down the best boss I’ve had, and I’ve had some good ones. I’ll never forget the impact she had on my career. At the time I joined Oracle and Mary-Lou’s team, my work career (~4 years) was average at best. I felt uncomfortable stating my opinions, especially with those more senior than me. She encouraged me to trust my analysis, speak up, and take risks. With her support, I grew from a somewhat diffident analyst to, in less than 2 years, a key Oracle leader talking to multiple CIOs in a given day. She epitomized “get it done and ask for forgiveness later.” That phrase is one that is used positively in Silicon Valley. Yet, on more than one occasion, I would hear people say that Mary-Lou was a bull in a china shop. I suspect they wouldn’t have used that term for a male colleague. I regret not calling out those people as Mary-Lou is as smart, aggressive, and fair as they come.

2 | Shilpa

I had never been a product leader, yet I was asked to take over two existing products at Oracle. Shilpa ran one of them and patiently helped me get up to speed and succeed. Frankly, she could have been resentful that some guy with no product management experience was now her boss. Two experiences with Shilpa come to mind. She taught me about customer empathy. I won’t shock anyone when I say that Oracle didn’t have the greatest reputation in the application industry. Yet, Shilpa showed me how to listen to customers, understand and empathize with their pain, and suggest paths to success. For startups, this is incredibly important. The first slide of almost every startup’s presentation (whether talking to prospects or fundraising) is about customer pain. Customers loved her and that was a huge accomplishment. A mega-customer, GE, actually made a Star Wars-themed video about how awesome Shilpa is. Name another product manager where that has happened. The second experience is one that is a guiding motto that I have used the rest of my career. I learned that work life is SO MUCH EASIER when you hire people that are smarter than you in their role. They attack problems, come up with solutions, and keep you advised of sticky issues. You end up spending so little time managing those employees and more time finding ways to expand their role. If your startup isn’t hiring Shilpa’s, then you won’t succeed.

3 | Casey

Casey is an awesome designer with a heart of gold. That’s what her LinkedIn profile says and it’s 110% true. She became the first UX designer at Coupa and cleaned up our mess. And she has gone onto way better things as one of the earliest designers at Uber, and the first one at Forward. Super talented, Casey was named one of the most powerful female engineers by Business Insider. But that’s only a small part of what makes her and her companies successful. She creates a culture that work is about people and developing relationships. Coupa was my fourth job in my career. A big Wall Street firm, a small strategy consulting firm, and Oracle. When I went to work, I worked. I knew my co-workers, but I didn’t really know them. Too much of my thought was on the end-work product. It wasn’t about the people and the process that went into it. In hindsight, I see that was short-sighted and potentially devastating for a startup. Startups go through way too many highs and lows, arguments, and controversial decisions. If you walk out of a heated internal meeting feeling like you “beat someone else,” it’s a bad sign.

Casey showed me that you build relationships inside and outside of the office. In relatively boring enterprise software company, she looked for ways to have fun and bring many people into those experiences. Some are obvious like going for drinks after work. Then there was decorating the office where she encouraged lots of people to come in and paint. She knows my family and they know her. Work isn’t a sprint measured by deliverables. It’s a community of people working together towards an often-changing goal. This is one area of development that I still have much work to do. Startups and life are about experiences and Casey defines that.

4 | Cynthia

Cynthia, or Cyn as she likes to be called, started working for me as a product manager and thankfully joined me at a second company. In Cyn I saw a mix of the successful attributes of Mary-Lou, Shilpa, and Casey. Plus Cyn possessed the control, discipline, and attention to detail (and a lover of the Oxford comma) under enormous pressure of a startup and crazy life at AWS. Bringing a new service to market with AWS is no small feat, and it’s mayhem on launch day. Cyn controlled our launch day and I had several leaders of other teams tell me how she was a rockstar.

Cyn is all about data. Yes, she made me look like an Excel newbie. But it is her ability to come up with hypotheses, find the data, and use it to put together smart business decisions is special. As an aside, when I started looking at evaluating moving to a new home, Cyn sent me a spreadsheet with the 39 criteria she used to evaluate a recent purchase. I’m so happy that she is now leading big teams at Zillow…and definitely not surprised.