2023 Best & Brightest MBA: Caitlin Piccirillo-Stosser, Yale School of Management

Caitlin Piccirillo-Stosser

Yale School of Management

“I am a mission-driven individual who is deeply passionate about solving challenging problems in education.”

Hometown: Ossining, NY

Fun fact about yourself: I Irish step danced for 10 years while growing up and competed at regional, national, and international levels.

Undergraduate School and Degree: The University of Chicago | BA Economics, BA Public Policy Studies

Where was the last place you worked before enrolling in business school? The Home Depot Pro (nka HD Supply), Senior Financial Analyst

Where did you intern during the summer of 2022? Bellwether, Strategic Advising Summer Fellow (remote)

Where will you be working after graduation? Bellwether, Consultant (remote)

Community Work and Leadership Roles in Business School:


Education Club: Co-President (2022-23), 1Y Leader (2021-22)

Women in Management Club: 1Y Leader (2021-22)

SOM United Soccer Club (2021-23)


Admissions Interviewer (2022-23)

Admissions Student Ambassador (2022-23)

Admissions Guide (2021-22)


Career Advisor (2022-23)

Which academic or extracurricular achievement are you most proud of during business school? As part of the Education Club at SOM, I had the opportunity to organize the Education Design Challenge, an annual case competition that the club hosts in partnership with the Design & Innovation Club about a dilemma related to education. It was incredible to be part of the planning process, from choosing a theme to identifying a partner organization to writing a full-length case. It took a lot of work, but seeing the event all come together in the end was so worth it. In 2022, we had about six teams of students from all across the university participate; I loved seeing the solutions they came up with in response to the case question, which was about reimagining pathways for marginalized students to get good first jobs. I certainly learned a lot, and I think that the student participants did too!

What achievement are you most proud of in your professional career? I think my proudest professional achievement was getting an internship during my first year of business school with an EdTech startup called Tutored by Teachers. I knew coming into business school that I wanted to pivot my career to working in education, but I also recognized that it was going to be a difficult process, since I didn’t have any professional experience working in education. However, when I was offered the position as an MBA intern with Tutored by Teachers, it brought that dream of working in education a little bit closer. It was not easy at times, balancing my internship with my classes, clubs, and other commitments at school. However, it was an incredible learning opportunity and I’d like to think that I made a difference in some of the teachers’ and students’ lives who Tutored by Teachers was working with and helping. I am so grateful to the team at Tutored by Teachers for giving me a chance and for being such a great group of mission-driven individuals from whom I could learn!

Why did you choose this business school? What brought me to SOM was, without a doubt, the people. Everyone I met throughout the admissions process was so kind and welcoming, whether it was current students, other prospective students, staff, or alumni. Community and culture are two of the most important things that drive my decisions around choosing where to work and go to school, and I could tell that SOM had a very inclusive, collaborative culture where I would be happy. Further, I wanted to be surrounded by people who were supportive of my career pivot from retail into education, and who would help me achieve those goals. Throughout my two years at SOM, I am constantly validated in my rationale, and I am so grateful to have such a wonderful community here.

What was your favorite course as an MBA? I’ve taken so many incredible classes during my time at Yale, so it’s really difficult to choose just one. However, I think one of my favorites was Strategic Management of Nonprofit Organizations with Professor Judy Chevalier. Not only is Professor Chevalier amazing, but the class was wildly intriguing. Since I’m going into social impact after graduation—and will not only be working for a nonprofit organization, but will be working with various nonprofit organizations—I had wanted to get a better understanding of how nonprofits work, financially, structurally, and operationally. The class provided all of that and more. Professor Chevalier had a great balance of lectures and guest speakers; I learned so much, and am now better equipped to support nonprofits in the future.

What was your favorite MBA event or tradition at your business school? One of my favorite events at SOM was our Winter Stroll in December 2021. It was essentially just a lot of food and drinks out in the courtyard at SOM, but it was the first big event with everyone together, since there were still a lot of COVID protocols in place. It was also the first event that partners were allowed to join, so I was really excited to bring my partner and to meet some of my classmates’ partners as well. Overall, it was just a great night to spend some time with friends, eat good food, and welcome the holiday season before we went on winter break.

Looking back over your MBA experience, what is the one thing you’d do differently and why? I try to make my decisions with as much consideration and thoughtfulness as possible. For the most part, I have been very pleased with my MBA experience. If there was one thing I could have done differently, it would have been getting more involved in the New Haven community. I often try to volunteer in the communities in which I live; when I lived in Jacksonville, FL prior to coming to Yale, I volunteered at an after-school reading program run by the YMCA. However, because I started school during the pandemic, many schools and nonprofit organizations were not accepting volunteers due to COVID concerns. I had to make some difficult decisions about how to spend my time outside of the classroom, like choosing to pursue an in-semester internship instead of doing pro bono social impact consulting through one of our clubs at SOM. Ultimately, I did not have time to also volunteer regularly in the New Haven community. Still, I feel that I have been able to give back to the community in other ways, such as participating each year in a 5K run for refugees through the local nonprofit IRIS and helping to organize a day of volunteering in a New Haven school through the Education Club. I look forward to being more actively involved in whatever community I move to after graduation.

What did you love most about your business school’s town? Many people would probably say the pizza is the best thing about New Haven. Since I grew up outside of New York and went to school in Chicago, I think the best thing about New Haven is East Rock Park. The park is a quick 20-minute walk from SOM and is a great mini-getaway from the hustle and bustle of downtown New Haven. Even the air feels fresher! Hiking up to the top of East Rock rewards you with beautiful views of the city and Long Island Sound. I appreciate the ability to relax and wander around the park, especially during the busiest times of the year.

What surprised you the most about business school? Something that I was not prepared for in business school was the sheer number of things happening at all times. There are so many events, speakers, and activities every week, not only at SOM but across the wider university; it’s impossible to go to everything. Sometimes there will be three different events happening on the same day at the same time and I want to go to all of them! Business school has been a lot about balancing priorities and making sure I set aside some downtime for myself.

What is one thing you did during the application process that gave you an edge at the school you chose? I’m not sure if it gave me an “edge,” but something that helped a lot during the application process was talking to current students. Having these conversations enabled me to better understand who the students were at Yale and what the culture was like. I was able to get a stronger sense of the community at Yale and realize that this was where I wanted to be.

Which MBA classmate do you most admire? This is so difficult to answer because I am surrounded every day by so many inspiring peers. If I had to pick just one, I would choose my Education Club Co-President and dear friend, Erica DeMond-Moriyama. Erica is an incredibly active member of the SOM community, not only through her leadership in the Education Club but also through her revival of the Running Club. She is similarly dedicated to improving education, and she couldn’t wait to get started doing so; she recently started a job (while still in school!) as the Operations Director at Edwell, an educator wellness startup launched by an SOM alum. In addition to her amazing leadership and professional successes, Erica is a wonderful friend and someone who I know I can always turn to when I am struggling with anything. Erica is a true embodiment of “business and society,” and I am so lucky to have gotten to know her well over the past two years.

What are the top two items on your professional bucket list? There have been problems in education ever since it started in this country, and attempts to solve those problems for just as long. I don’t expect to find a silver bullet that will magically fix every existing and future issue, but I do hope that the work I do can make educational experiences and outcomes at least marginally better for students across the country and around the world. Two of the areas in which I hope to achieve this are the following:

  1. Distributing funding and resources equitably to all students, teachers, and schools
  2. Creating systems, schools, and policies to enable all students to dream

What made Caitlin such an invaluable addition to the Class of 2023?

“Caitlin Piccirllo-Stosser is the club leader for SOM’s Education Club. She exemplifies the usefulness and importance of SOM’s mission “to educate leaders for business and society.” In her capacity as Education Club leader, Caitlin has brought to fruition a new partnership between SOM students and Junior Achievement of Southwest New England that seeks to positively impact New Haven’s youth. Caitlin and her fellow leadership team promptly took charge of the making this partnership happen. Most importantly, she helped ensure that SOM put forward a robust team of diverse volunteers for our first JA Day, recruiting almost 50 students, staff, and faculty to participate. I know Caitlin seeks to transition her career post-SOM into education, and it was a joy to watch her take this opportunity to gain valuable experience in New Haven Public Schools that supports her own goals, but also to identify their alignment with the School’s goals of growing our engagement with New Haven.”

Lauren Zimmerman
Chief of Staff 

“All of our MBA students are busy – that simply comes with the territory. However, every once in a while, a student somehow exceeds what I thought was possible in terms of time management. That’s Caitlin. Whether she is leading admissions tours, helping to train incoming first-year Admissions Guides, having lunch with prospective students, or participating in the million other ways she has over her two years at Yale SOM, she always makes it seem like there is no other place she would rather be. Caitlin has been wonderful to work with and I have no doubt she will continue to be a valued member of the community as an alum.”

Kate Botelho
Senior Associate Director Of Admissions


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