As a part of our interview series called “Women Of The C-Suite,” we had the pleasure of interviewing Megan Meyer Toolson, Chief Customer Officer.
Megan is responsible for go-to market efforts, including marketing, sales and support, in-market operations, and in-market expansions. Since 2015, Megan has served in multiple operational and leadership roles at Opendoor. Most recently, she was the Head of Operations, overseeing the day-to-day centralized and local activities required to efficiently buy and sell thousands of homes per month.
Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
Growing up I was lucky enough to watch both my parents succeed in careers they loved — my mom as a teacher and my dad as a master planned community developer. As I started to think about my career, I knew from their examples I’d be happy to work hard as long as I was building something that would make a lasting difference.
Fast forward (some) decades later; when I had the opportunity to join Opendoor back in 2015 I was drawn to the impact we could have on families, communities, and economies across the country by empowering a seamless move. For me, it doesn’t matter the particular work I am focused on (and that changes all the time anyway at a startup), because the mission is something I can dedicate countless hours to and be proud of at the end of each day.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
Hard to pick just one, but starting out I definitely thought I had learned everything I would ever need to know about home improvement from my thousands of logged hours watching “This Old House” and HGTV. I assumed that every kitchen remodel would turn out flawlessly more or less “after this commercial break” with limited planning or design iteration.
I had one particularly terrible experience where I left it to the contractor to choose a bath tile and he picked a very particular patterned clay that a few buyers would adore and most would hate. Despite our substantial investment, the house took months to sell because we hadn’t invested in planning and design up front.
I learned a bunch from that experience: 1) to always keep my end customer in mind when making decisions (even a decision to delegate); 2) that planning up front can save lots of pain and headaches for “future me”; and 3) of course nothing is as easy as it looks on television.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
I’ve been incredibly lucky to have many traditional mentors over the years, including three female bosses who all had an enormous impact on me personally and professionally.
Some of the most significant growth periods for me have also come from peers and colleagues who challenged my thinking — even the ones I thought I would never find common ground with.
Early on in a startup, stress can be high and the lack of structure, process, or even hierarchy can lead to a lot of highly impassioned debates. What I learned from those moments and those teammates was how many different ways there are to approach problems, and that real innovation is impossible without a lot of disagreement along the way. I also learned to always question my beliefs from multiple angles to try to find alternate, better solutions.
In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?
I’ve learned over the years that almost everything gets easier and less stressful with practice and repetition. I used to get so nervous before big presentations or critical conversations that I’d beg to get out of them. Now, I use a little mantra called “don’t wing it” (it comes with a hand signal of flapping your arm like a bird). Preparation and thoughtfulness in advance helps me exhale, relax, and be present in the most critical moments.
As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?
To start, diversity of experiences drives diversity of thought, creativity and ultimately innovation that will lead to better business performance.
Diverse teams also better reflect the (likely) diversity of a company’s customer base, helping them to more deeply understand and build for the users of their products.
Finally, diversity at the highest levels of leadership creates role models for exceptional talent throughout the organization who can grow into future executives.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?
Executives are tasked with putting together and conducting the orchestra, but not playing any particular instrument. They need to deeply understand the music, the instruments, the musicians, and the audience and how it all works together, but will be a master of none of those things alone. Importantly, an executive’s most important role is inspiring and empowering the talent around them to work together toward a common ambition that initially seems entirely unrealistic.
What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?
A lot of people think executives exist to have all the right answers at every turn. In reality, an executive’s role is to ask the right questions and support his or her team in finding those answers. My mom used to have a poster in her classroom titled, “Everything I Need to Know I Learned in Kindergarten” and I think that holds true for my role today. Always ask why, practice makes perfect, treat others the way you’d want to be treated, and don’t forget to cross your t’s and dot your i’s.
In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?
I think a real challenge is a lack of role models. When I was younger in my career I received feedback that I was visibly trying to emulate an older male executive, and it didn’t work for me because I was a young woman so I was losing trust and influence.
There are so few female executives it can be hard to look around and see a picture of what to aspire to that is authentic, achievable, and relatable. We’re left to piece together elements from various places and hope we can breathe life into something that works.
What is the most striking difference between your actual job and how you thought the job would be?
I think the biggest difference is that there is no one version of the job every day. I thought I would always be thinking 6, 12, 18 months ahead and helping the organization plan and build capabilities for future success. The reality is some days I am doing that, some days I am focused 1 inch in front of my face to help my team hit a milestone, some days I’m a professional therapist, others a networker and recruiter, and other days I’m just a blindly optimistic cheerleader.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
“If everyone else jumped off a bridge, would you?” This one still echoes in my head from childhood and I think about it all the time.
For me, having a unique and clear perspective has been one of the most important parts of my journey and something I deeply respect in colleagues and teammates. I’ve found it’s rarely possible to accomplish something noteworthy by modestly tweaking what everyone else is doing. At the end of the day, no matter what my peers say or think, it’s me who will need to own and live with my decisions. The most brilliant accomplished leaders in any field can’t know my customer or business well enough to know exactly what the right answer will be for our situation.