Alumna Spotlight: Kaley Pillinger ’21 B.A., ’21 M.A’s Road from Dwight Hall to Stanford

Originally from New York City, Kaley Pillinger ’21 B.A., ’21 M.A., was recently awarded the prestigious title of a Knight-Hennessy Scholar. Kaley is pursuing a master’s degree in business administration from Stanford Graduate School of Business while concurrently earning a J.D. at Yale Law School. During her time at Yale, Kaley graduated Phi Beta Kappa and magna cum laude with a double major in economics and history, in addition to a master’s degree in history.  

Kaley’s interest in public service began while growing up in New York City, where she witnessed her neighborhood change and saw how her community responded during periods of transformation. Connecting with the community around her became one of the most formative influences on her goals and ambitions. When she arrived at Yale, Kaley was eager to learn more about New Haven and its similarities to New York as a city undergoing change, while also discovering her own role within the broader community. At the Service Bazaar, she found that opportunity through Dwight Hall. 

At Dwight Hall, Kaley explored academic interests and gained professional experience by serving local New Haven organizations and working as a Dwight Hall Urban Fellow. As an Urban Fellow, Kaley worked with Neighborhood Housing Services of New Haven (NHS), where she had the opportunity to work alongside the executive director. At NHS, Kaley deepened her interest in housing while directly getting to understand people’slived experiences and the meaning of equity. 

“Being at NHS gave me a profound understanding of New Haven’s housing ecosystem through directly working with residents. I saw how first-time homeownership could be a pathway for people to build wealth, power, and more just systems within the city. Growing up in New York, where the majority of residents rent their homes, I hadn’t had as much exposure to homeownership initiatives or the role they can play in creating long-term economic stability and opportunity.” 

After her graduation at Yale, Kaley worked in real estate at Blackstone and in affordable housing development at Fairstead, where her responsibilities included a $600 million renovation of an 87-building portfolio in Brooklyn. 

Kaley came back to the Hall in 2025 where she was a panelist at the “Young Alumni in Social Impact Careers Panel,” hosted by the Alumni Mentorship & Career Development Task Force. Kaley and her fellow panelist offered insights for the 16 students in attendance, a glimpse into dynamic social impact careers and practical guidance on leveraging college experiences to forge meaningful paths after graduation. 

Now, Kaley is excited to return to academia at Stanford. 

“I feel lucky to be going back to graduate school and pursuing a business degree at Stanford. School gives you the opportunity to explore different roles and ideas in a way that’s much harder to do once you’re fully immersed in the working world. Being part of a program that emphasizes creativity in the realms of social justice and public service has been especially meaningful because you’re surrounded by peers who are also committed to making an impact.” 

For those eager to use their skills, she encourages students and anyone willing to engage in service to engage with New Haven, emphasizing the importance of spaces like Dwight Hall that have been formative in her own growth in public service. Kaley also advises individuals to stay open to learning, emphasizing the importance of starting with the impact that they hope to create and build the skills and experiences needed to achieve it.  

“I try to begin by imagining the ideal version of the world. While we often have to make trade-offs in the real world, I think it’s important to first ask what the best possible outcome would look like—whether in housing or other essential areas of service—and then work toward that vision in whatever ways are possible. Even if we cannot achieve that ideal immediately, the goal is to keep moving in its direction.” 

Kaley’s Dwight Hall experience embodies the Grow pillar of Dwight Hall’s EngageGrow, and Advance program delivery model, developing students’ intellectual, moral, civic, and creative capacities to the fullest with experiential learning, internships, fellowships, mentorships, and training.  

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