A Conversation with Venture Advisor, Kyle Bailey
Kyle Bailey is the Senior Director of Engineering at Cash App. He brings more than 15 years of startup experience to GCVC — previously holding positions at AirBnB (Head of Engineering for AirBnb.org), Uber (Software Engineer, Manager), and AirWatch (Engineering Lead) acquired by VMWare for $1.5B. Kyle hails from Detroit, Michigan and holds a B.S. in Computer Science from Michigan State and an MBA from Wharton. We caught up with him last week to get his take on leadership during the pandemic and diversity in the workplace.
Question: How did you meet our GP, Maggie?
Kyle Bailey: Maggie and I met through our Wharton MBA program. She’s one of my favorite people. In fact, I would make sure to sit near Maggie when we shared classes because not only was she the most prepared of our classmates — she was absolutely hilarious too. She always paired her extremely thought provoking comments with some totally unexpected one-liners.
Q: With more competing priorities for your time than ever, we are so lucky to have you as a VAN member. What about the GCVC portfolio companies excites you the most? Is there something you are particularly eager to work on with them?
KB: I’ve been at startups for my entire career because I believe founding companies — creating something useful in the world that didn’t exist before — is one of the most valuable things to do in life. To me, talking to founders is rewarding in itself. I get excited hearing about the passion, creativity and lessons required to make something from nothing. I’m happy to help walk through general management challenges, hiring, roadmap questions, technical issues and anything I’m between.
Q: We believe everyone in our herd has a superpower, what is yours?
KB: This is an interesting question as I wouldn’t say any specific skill but rather the unique intersection of all of my experiences. I believe innovation happens at either the intersection of disciplines or through serendipity. For me, coming from a diverse blue collar town (Detroit), having a background in art, deeply understanding computer science and studying business helps me to innovate more consistently and relate to a wider array of people.
Q: You’re currently at CashApp. What changes did you make in how you managed your teams to adjust to remote work in 2020? What worked and what won’t make the cut for 2021?
KB: My top issues managing teams remotely have been building community and dealing with the stress of COVID. I don’t know if anyone has really figured out how to do either of them that well but we’ve found some success encouraging our teams to take time off even if they don’t go anywhere. Also, no one is really operating at anywhere close to 100% right now. There’s a lot going on in the world. You have to let people know that’s ok because not knowing if they’re living up to expectations can cause even more stress.
Q: You founded the Black Employee Resource Group at Uber. How early in a company’s life cycle should leadership consider implementing a similar resource/group? What other wisdom can you impart to founders looking to promote diversity and inclusion? Where should they start?
KB: D&I has such an underrated impact on a company’s business — it’s become a secret weapon. You can look at companies like Clubhouse and TikTok and see how appealing to diverse communities drives serious business outcomes. I wouldn‘t worry about building formal ERGs until you’re a very large company but you should start early in building inclusion — finding ways to involve all of your team in decisions and culture — and hiring diverse members — giving those diverse use cases a seat at the table as you build your products. It just makes sense to have the communities or your customers build products with you.
Q: Is there a book/show/movie that you have read/watched during the pandemic that you would recommend to our community?
KB: I finally finished Sapiens — which I highly recommend — but I’m sure everyone may have already read that. One of the most stress relieving shows that I’ve been watching are old episodes of Grand Designs on YouTube. The show follows English, New Zealand and Australian home owners as they build their dream houses over a few years. There’s no drama, only really nice homes, so it helps me escape, learn a bit of architecture and appreciate people’s creativity.
Q: What is the first place you want to travel to once everything is open and safe?
KB: Straight to my mothers home to give her a hug. It’s been a strange year and nothing has been stranger than not being able to hug my mom. I’m looking forward to her visiting me in NY and spending a lot of time together.
