Kelly Kay serves as President and Chief Operating Officer for YapStone, where she oversees the day-to-day operations of the company. With over 15 years of global payment and regulatory experience, Kelly brings vast international experience to the YapStone team. Before joining YapStone, Kelly played key legal and government relations roles at PayPal, MasterCard, eBay, Banc One, and the Wikimedia Foundation. Her career-long payments expertise helped to drive PayPal’s expansion throughout Asia Pacific including Singapore, Hong Kong, Australia, Taiwan, Philippines, India, and Malaysia.
How has your life experience made you the leader you are today?
I have a great love of change and adventure that stems from a childhood of moving from place to place. This has often made me the first to jump into projects that seem like a lost cause, and many of these have led to some crazy adventures in the law, forcing me to step up and into various positions of leadership.
Throughout my career, I have also worked in various countries throughout Asia and Europe. The opportunity to deal with different cultures and management styles was an enormous learning opportunity. Imagine being a six-foot tall American woman presenting to a room full of regulators from Japan, Thailand, Malaysia, Singapore, Taiwan, China and the Philippines. Many of these countries have cultures where women are not part of this type of work. It was a challenge to win them over and get them to listen, trust and engage with me, as well as see me as an expert and leader in the payments space. But in the end, knowledge, creativity and friendship led to amazing working relationships that made it possible for me to succeed in the tasks I was given.
How has your previous employment experience aided your position at YapStone?
I’ve been working in the global payments industry for over 15 years. At PayPal, I built and subsequently led the International Legal and Compliance team focused on bringing PayPal’s online payments business to Asia Pacific at a time when laws did not exist that applied naturally to the services we offered. It was an amazing time to be in the payments space and gave me an opportunity to work closely with regulators throughout Asia. After PayPal, I joined MasterCard in Singapore as the Head of Public Policy and Regulatory Affairs playing a similar role. I started my career at Banc One Corporation (now JP Morgan Chase) at a time when no one knew where the Internet and banking would intersect, but there were some great ideas and I was lucky to get to help bring them to life.
YapStone is a natural fit for me. It is fast-growing, faces similar challenges to my other roles, and is giving me a great opportunity to build a team of driven, hardworking people all working towards the same goal.
What have the highlights and challenges been during your tenure at YapStone?
YapStone has been an amazing adventure. No day is the same. The co-founders of the company — Matt Golis and Tom Villante have given me some great opportunities to lead in areas like Risk and Fraud, Human Resources, Security, as well as Legal and Compliance. My willingness and desire to step in and do anything has brought me face-to-face with some interesting challenges – some I never dreamt I would have – and some amazing rewards. And now I’m helping shape and lead one of the fastest growing companies in the payments space.
How is YapStone changing the online payments industry?
Our goal is to change how people pay for everyday expenses by making it simpler and easier than it has traditionally been. We focus on industries that are currently dominated by paper checks. For example, YapStone powers online marketplaces like HomeAway and VRBO. We also simplify how people pay for rent, vacation rentals and charitable donations by providing online and mobile payments solutions.
What advice would you give to women who are looking for a career in a similar industry?
What I tell my team, and what I have always lived by, is to remember to do what no one else is doing. Pick up the project that no one else wants to touch and shine. The others did not take it for a reason; either it was outside their comfort zone, too hard, or just not possible. Through this, you can show you are willing, confident and creative. And just imagine the looks on the naysayers’ faces when you succeed where they were afraid to tread.
How do you maintain a work/life balance?
Work/life balance is a hard lesson to learn. I lost a lot before I learned the value of it. Earlier in my career, my mom told me I should quit my job so I could have a personality again. While I did not listen to her about the job, I did take her comment to heart and started taking time to do the things I wanted to do. I got my Skippers License (a two year project!) from the Royal Yachting Association and started organizing yacht trips for my friends and I in Thailand, Greece and Croatia.
I also took up kickboxing and found an excellent instructor in Singapore that taught me to kick some butt. It’s a great stress reliever! Now, when one of the co-founders comes to pull me out of a meeting, they think twice!
What do you think is the biggest issue for women in the workplace?
There are two issues that come to mind for me based on what I’ve observed. First, in business, it’s important for women to stand up for what they believe in and be able to effectively and persuasively argue their case without being overly emotional. The other challenge for women is the perception that they are too distracted by home life and kids to be a reliable part of the team. Work and family should not be mutually exclusive.
How has mentorship made a difference in your professional and personal life?
Mentors have played an important role in my life and in my career. John Muller, who was the General Counsel at PayPal was a great mentor and role model for me. He taught me to use intelligence in leadership, to be firm in my convictions, be flexible, and to listen to my team as they usually know more then me.
Which other female leaders do you admire and why?
I found the women leaders of the Wikimedia Foundation to be amazing. If there was ever a world driven by men, it is the open source and free knowledge space we lived and worked while at Wikimedia. Gayle Young, Sue Gardner, Michelle Paulson and Patricia Pena are all amazing women who work tirelessly to give women a place in one of the most amazing worldwide free knowledge movements. I was proud and lucky to work alongside them and all the other women at the foundation.
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