Interviewed by Brooke LePage ‘19 

BL: What have you done since leaving Trinity?

AW: When I graduated from Trinity I thought I wanted to own a restaurant, so I went and worked in two restaurants. One was in western Massachusetts and the other was back in New York City, where I’m from. I cooked at the restaurant in Massachusetts and worked on the business management side of the one in New York. After nine months, I realized I actually did not want to own a restaurant after all. I loved hospitality and service, but it didn’t feel like the right fit for me. So, I consulted alumni; I don’t know if you have any friends on the football team, but we have a really strong alumni network. 

BL: My best friend’s dad was on the football team and he comes back all the time to talk and network with current student-athletes.

AW: Yes, it’s an amazing network. It’s a pretty special thing, and I know that. I was in a LinkedIn group and I got introduced to Christian, an alum who graduated in 2005 or 2006. He was also a football player who was working for a startup delivery service. The head coach of the football team at Trinity put us in touch, and it was initially a conversation where I was trying to convince Christian to get my restaurant on this delivery platform. He actually ended up offering me a job working on operations, customer support, and restaurant support for a tiny ten-person delivery company. In 2014, we got acquired by Square, which is what is being used when you see people taking credit card payments on phones. I moved to San Francisco where Square is headquartered, and we began growing from a team of ten people to about two hundred people now. Then I moved from Square to a product called the Cash App, a peer-to-peer payment app similar to Venmo. Cash App has a lot more features, though, and I work on our college marketing team where we’re trying to figure out how to expand to campuses like Trinity where Venmo is the dominant product for sending and receiving money amongst classmates and peers. Our focus is on the best marketing strategies for converting a campus like Trinity from Venmo and to Cash App, which we think is a superior platform. I’ve been here for just over five years now. I absolutely love working for a really cool technology company. Starting at a company with only ten people, it’s pretty massive growth both personally and professionally. 

BL: That’s awesome. Is there anything you learned at Trinity that you’ve used in your career? 

AW: I took a course at Trinity with Professor Chambers that dealt with issues of urban education and as part of that course, I had an internship and a group project where I worked with an organization in Hartford called the Achieve Hartford. It was an advocacy organization for Hartford Public Schools. I learned about issues in urban education, and I also mentored with members of the football team at the McDonough School just a couple blocks away from Trinity. My personal interest was in Urban Politics and Urban Education, so being right in Hartford really let me explore that. What I’m doing now is totally unrelated to political science but the cool thing about a Liberal Arts education is my jobs have always been about finding a problem and really digging deep to learn more about it. How do we best go about solving that problem? I link that back to my Trinity education; when you have to apply yourself to learn things that don’t seem related to each other and solve problems, that’s exactly what I do on a daily basis. 

BL: I think a lot of students have trouble verbalizing the value of a Liberal Arts education, so that’s a great way of putting it. My last question is, what are some of your hobbies, passions, accomplishments, or anything that you would like Trinity to be aware of?

AW: Football. Football is core to my experience at Trinity. I was a three year starter on the team, played all four years, and I was a captain my senior year. And we won! We came in second place in the NESCAC championships my first three years, so I’ll never forget closing out my football career after winning on a beautiful November day at Wesleyan. I will never forget that day. It was an unbelievable feeling to work incredibly hard for something over the course of four years and have it all culminate with this awesome experience. All my best friends who didn’t play football all came that day and watched and celebrated with us afterwards. I think about that moment when I look back, having all of my best friends and so many people who are still a huge part of my life. They were all there celebrating, happy for me and our accomplishments as a team. That was so so so memorable. I also remember all those days I did student calling…

BL: I did too!

AW: In that room with no windows right?

BL: Yes! Exactly.

AW: I remember speaking with alumni when I worked as a caller and I always thought that people’s connections to Trinity after graduating was really special. It was something that I really hoped for. So after  graduating and being offered this job through my football coach and another Trinity alumnus, I feel a really strong responsibility to give back to Trinity — not just by giving money, although I do give money directly to the football team every year. Some of my proudest moments post-grad have been landing young Trinity football players jobs at my company. I think Trinity has the most passionate, engaged, and amazing alumni base. Being able to return the favor has meant a lot to me. 

BL: That’s amazing. It sounds like the football team alumni network is a great model for the college as a whole.

AW: When I graduated, there were fourteen seniors on the football team and we all got jobs. I think eleven of the fourteen got jobs with a Trinity Football alum. It’s amazing. I love Trinity. It really is an amazing place.