Building Power Collectively with VEST Member Casey Williams, COO at Fenway Summer Ventures.


"Don’t act the part. Be authentic in your approach and have confidence in what you uniquely bring to the table."

VEST Member Casey Williams is the COO of Fenway Summer Ventures, an investment and advisory firm based in Washington, DC. Casey has worked in finance and entrepreneurship across the country, as an R&D analyst at Wells Fargo in San Francisco, California and as a manager for the non-profit Kiva Microfinance U.S. in Tulsa, Oklahoma. Her work with Kiva earned her the 2018 Financial Service Champion award from the Tulsa SBC, as well as Entrepreneur of the Year from Tulsa Young Professionals. Prior to her work in financial services she spent two years as a fourth grade math teacher through Teach for America.


Tell us more about your current role and why you chose to lead from this perspective.


I’m the COO of a venture capital firm based in Washington, DC focused on early-stage fintech companies. We’re a unique organization in that we are willing to invest in, advise, and even build companies that we believe should exist and will be successful. I joined venture because I wanted to be part of an industry that can make real changes, where you can literally put your money where your mouth is. My role covers the day-to-day aspects of keeping a company running, but also gives me plenty of opportunities to research solutions to financial problems and meet with entrepreneurs who have dedicated their lives to solving these problems, which is and incredibly rewarding way to spend my time.


What’s been the most challenging part of building your career?


The uncertainty. My older sister is a surgeon and I have always said that I envy how clear cut her path has been, that she knew what she wanted to do and all the steps to get there were clearly laid out for her. I’ve since learned that it’s not that easy for any of us (even doctors), and almost everyone I’ve spoken with--no matter how advanced or successful in their career--still doesn’t quite know what they want to do when they grow up. We are all just figuring it out as we go, and even though that can be a stressful experience it’s also a great gift that we don’t have to stay in the same company or industry for decades in order to rise through the ranks, and that we have autonomy in determining our own way forward.


Do you have a unique experience that changed your perspective in life?


My first job out of college was as a corps member for Teach For America, where I taught 4th grade math in a Title I school. Nothing has shaped my understanding of the world around me more. Teaching kids who grew up in a completely different environment than the one I was raised in really built my ability to empathize with others, and helped me identify my privilege and the opportunity gaps that exist for so many people. It also gave me the courage to be an advocate for change, and I’m so grateful to have gained that early on in my life.


What are your top two values? Why?


Hard work and curiosity. I think both are necessary to living a fulfilling life, and that they balance each other out. I love surrounding myself with people who are inquisitive, who listen and seek to understand, and who take what they’ve learned and use it to make things better, which takes a solid work ethic!


If you could go back in time, what advice would you give yourself upon starting your career?


Meet as many different people as you can, in your current industry and in any other industry that interests you. Meet people who inspire you even if they do things you would never be interested in doing, and meet with people you wouldn’t normally interact with. Ask them questions and use each conversation as an opportunity to think about your own answers as well. I would tell myself to do less “networking” and more relationship building.


What's the worst advice someone has given you?


When I started as a COO I was given the advice to “act the part.” I was encouraged to act like what a COO “should” be like: someone uber-professional, analytical and rigid. I am none of these things, but I’m a successful COO because I’m organized, efficient, and a fast learner. I’m also a fast-talking energetic person who enjoys nerdy jokes and struggles with mental math, and if I tried to hide those qualities in order to appear more competent I think it would have been a real disservice to myself and my company. Don’t act the part. Be authentic in your approach to your role and have confidence in what you uniquely bring to the table.


If you could change one thing about the challenges women experience at work, what would it be and how would you change it?


One explanation of DEI that has always resonated with me is that diversity is who is sitting at the table, equity is who is talking, and inclusivity is who is being taken seriously. I think in all aspects of life, we need more women to be taken seriously, and it’s our collective responsibility to look at the tables we sit at, whether it’s in a boardroom or PTA meeting, and consider what we are doing to ensure everyone is being taken seriously.


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