Alumni Spotlight: Caroline Crosbie ’20L Caroline Crosbie is an associate in the New York Office of Simpson Thacher.

Caroline Crosbie ’20L

Caroline Crosbie ‘20L was born in Woodbridge, Virginia and grew up in Manassas, Virginia. She graduated from James Madison University in Harrisonburg, Virginia in 2017, where she majored in international relations with minors in political science and French. Before attending law school at W&L Law, Caroline was an intern on Capitol Hill for Representative Robert J. Wittman, the U.S. representative for Virginia’s 1st congressional district. In law school, Caroline interned for the Chief Staff Attorney of the Supreme Court of Virginia, Woods Rogers PLC in Roanoke, Virginia and Cleary Gottlieb Steen & Hamilton LLP in New York City. During her 3L year of law school, she worked in the Advanced Administrative Litigation Clinic (Black Lung). Caroline currently works as an associate in the New York office of Simpson Thacher & Bartlett LLP, focusing on commercial real estate financing. Outside of work, Caroline enjoys exploring New York City, spending time with friends and family, and watching reality TV.

Discuss your career path and how it led to Simpson Thacher & Bartlett.

When I began my 1L year at W&L Law, I was uncertain about the specific direction I wanted my career to go in, but I knew I wanted to pursue a path that would be intellectually stimulating and offer plenty of opportunities for learning and growth. My favorite 1L classes were Contracts, Civil Procedure and Property, which led me to seek out experiences during my 1L summer that would expose me to both litigation and corporate work.

During my 2L summer at Cleary Gottlieb, I continued to explore both litigation and corporate matters, and it was there that I first had the opportunity to work on a real estate transaction. I quickly developed an appreciation for the often collaborative nature of corporate work in contrast to the adversarial dynamics of litigation. I found that junior associates played a vital role in moving deals forward and often had the opportunity to engage in close client contact, which further piqued my interest.

Ultimately, I chose to focus on real estate due to the wide range of complex transactions real estate work entails, as well as the tangible nature of the work product –  there was something very satisfying about seeing the physical property that was the subject of my efforts. In June 2024, I lateraled to Simpson Thacher, where I now specialize in lender-side commercial real estate financing.

What sort of legal issues do you handle on a day-to-day basis?

I represent institutional lenders in commercial real estate financing transactions and deal with all issues that arise during the course of a financing and life of the loan. When originating loans, I draft and negotiate the terms of the various loan documents and review diligence matters related to the property and parties involved. I also work on foreclosures, loan modifications and workouts. One of my favorite things about real estate work is that no two properties are exactly alike, so each transaction I work on presents distinct challenges and opportunities that stem from the specific characteristics of the properties involved.

What do you like about your current job?

One of the things I like most about my job is that the complexity of the transactions I work on  provides me the opportunity to continuously learn and grow. Since I started my role as a real estate attorney, I have had the chance to work on incredibly interesting deals that require me to stretch my knowledge and creativity, and whenever I feel I have mastered one challenge, new and unique issues emerge, pushing me to expand my skill set.

What are some practices you have in your daily life as an attorney to maintain wellness?

Whenever I am feeling overwhelmed at work or completely lost on an assignment, I find it helpful to switch gears and work on something easier for a while, whether that’s a simpler task on my to-do list or just getting an errand done. This allows me to still feel productive but I’m able to come back to what I was working on with a clearer head.  It’s also important to me to unplug entirely when I’m able to by doing something that takes me completely out of work mode. If I need a real break during the day, some of my favorite ways to unplug are by calling family, catching up on a TV show, or going for a walk when it’s nice out.

Which W&L classes and/or experiences do you think were most helpful in preparing you for this job?

Working in real estate finance, property class was helpful for understanding the basics of real estate, and it was one of the most interesting and engaging classes I took during my time in law school. Also, having the opportunity to participate in some of the many substantive extracurricular activities at W&L Law, like working on a journal, participating in student organizations, and being a research assistant, helped me develop time management and organizational skills that are critical for my current job.

What advice do you have for prospective law students?

One of the best things about W&L Law is the strength of its community, and I can’t emphasize enough how important that community continues to be after graduation. The connections I made during law school continue to make up a large part of my professional network and support system. There are a lot of factors to consider when selecting a law school, but as you weigh your options you should take into account how engaged the students, faculty and alumni are with each other. Also, once you get to law school, while classwork and studying are very important, you should make an effort to engage with your classmates and the larger law school community and attend social and professional events. Not only will this make law school a more enjoyable three years, but those connections you make will be invaluable for the rest of your legal career.

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