Caroline McCaffery ’00, CEO, ClearOPS, Inc.
Caroline McCaffery '00 is the CEO of ClearOPS, Inc., a company dedicated to enhancing privacy and security for tech companies. Her experiences at NYU Law played a formative role in her journey and career path, marked by exploration and adaptability including time as an associate at Gunderson Dettmer and as General Counsel at Sailthru, Inc. Her advice to students: embrace diverse experiences and projects to uncover their potential. Read more below.
---
What made you decide to pursue a career in entrepreneurship after NYU Law?
Upon graduating, I joined a law firm called Gunderson Dettmer. I joined because of the people, but I found that the work they did, working with technology startups, really inspired me.
How did NYU Law prepare you for this career?
When I attended NYU Law, I had one class and one clinic that really impacted me. The class was Corporations, and the professor had us launch our own corporation. He asked for volunteers, and when no one volunteered to be the CEO, I did. We sold NYU Law hats, which I remember vividly. The bookstore, from which we needed permission to use the NYU Law logo, told me that they rarely sold any hats. Our design enabled us to sell out within a couple of hours on the first day, and we were able to return a dividend to our “investors”—our classmates and the professor. The clinic that influenced me was the Prosecution Clinic in the Bronx. At the time, I was considering going the public interest route but that clinic helped me decide that I was not meant for litigation. Sometimes it is the unexpected that drives your career path!
Why do you think lawyers find success in this career path?
I think certain lawyers who can balance the risk taking are very well suited for entrepreneurship because of our breadth of skills, particularly in judging risk.
What was the biggest challenge you faced as a lawyer in this career path?
When you tell people you are a lawyer for a tech startup, you are faced with an immediate bias that you are not suited, since lawyers are presumed to be non-technical and to “not do math.”
What is the most important thing students should do while they are still in law school to prepare themselves for a career in entrepreneurship, in venture capital, or at a start-up?
To take a variety of classes and explore the outer realms of what they are capable of, whether that is through summer internships, clinics, or taking on unique class projects.
What was the most important lesson you learned in your career thus far?
That my career path was not, and is not, linear, and that is actually quite fun.
---