A Career Built Beyond the Courtroom - a Q&A with Cynthia Carter
Cynthia Carter is the Vice President of Claims at Berkley Select and a member of the National Association of Women Lawyers (NAWL). She has an extensive background managing complex professional liability exposures to law firms large and small. In this Q&A written by NAWL, she tells us her career journey, what drew her to pursue law, and where she finds fulfilment and inspiration.
What made you want to become a lawyer?
For as long as I can remember, I’ve been drawn to the law. As a child, I was a voracious reader, especially of mystery and detective books that culminated in civil or criminal cases. I was endlessly fascinated by the courtroom scenes—the unfolding of facts, the strategy, the advocacy, and the pursuit of justice.
Even then, something about that environment felt like a place where ideas, fairness, and human stories came together in powerful ways.
In high school, I joined the mock trial team, which proved to be a defining experience. It was the first time I saw how legal analysis, preparation, and advocacy could shape outcomes. It made the profession feel not only compelling but also attainable. When I reached college, I minored in what was then called Women’s Studies—now Gender Studies.
Those courses introduced me to deeper discourse about women’s roles in society and pushed me to think critically about systems, equity, and structural challenges. They taught me to analyze, to question, and to situate issues within a broader sociological framework. By that point, law school was the natural progression for me.
Looking back, each step layered together to confirm the path I envisioned for myself. They helped shape not only my decision to become a lawyer but also the way I approach the work today.
What do you enjoy most about being a lawyer?
What I enjoy most about being a lawyer is the versatility the profession offers—a quality I did not fully appreciate in law school or even at the beginning of my career.
Over time, I’ve come to value just how dynamic a law degree can be. In my current in-house role at an insurance company, I’m regularly faced with new and complex challenges. Much like in a litigation environment, my work still centers on strategy, problem-solving, and advancing our organizational objectives. But the context is broader, and the opportunities to innovate are constant. I’m learning new things almost every day—about the business, about the industry, and about how legal strategy can help shape outcomes. That continual growth is what I find most rewarding.
Being a lawyer means evolving, adapting, and expanding your perspective as new issues emerge. It’s a profession that never stops stretching you, and I appreciate that it has allowed me to develop in ways I couldn’t have imagined early in my career.
What is your biggest challenge right now, and how are you working to overcome it?
One of my biggest challenges right now is keeping pace with the rapid evolution of AI and emerging technology and determining how to integrate these tools thoughtfully to create meaningful efficiencies in our work.
AI is inherently complex and evolving so quickly that what feels groundbreaking today can become outdated in a short time. With countless vendors and solutions promising transformation, it requires careful discernment to distinguish tools that truly add value from those that are more hype than substance—while also balancing information security, data privacy, and regulatory obligations in an industry that handles sensitive information every day.
Equally challenging is successful implementation and adoption across the organization. Integrating new technology requires more than training; it involves behavioral change and genuine buy-in to new ways of working. I view this as both a technical and leadership challenge—not just adopting AI, but using it in ways that support sound judgment, enhance decision-making, and improve outcomes. We are addressing this through a deliberate, collaborative approach with vendors, IT and security teams, and, most importantly, the members of my team who use these tools every day, with the goal of sustainable progress in an ever-changing landscape.
What has your career path been like?
Like many attorneys, my career path looks nothing like what I imagined when I was younger. I never had my “Perry Mason moment”—and despite all the legal thrillers I devoured growing up, I have never actually tried a case.
My early career was shaped largely by the opportunities available when I graduated from law school, and those opportunities ended up steering me in a direction that I did not predict but am grateful for.
I started my legal career in an insurance coverage practice where I represented Lloyd’s syndicates in relation to healthcare accounts here in the United States. It is a relatively niche area of practice and presented somewhat of a steep learning curve, but it gave me an exceptionally strong foundation. That experience taught me how to analyze complex issues, navigate risk management and the insurance industry, and develop a deep understanding of coverage principles. I didn’t know it at the time, but those skills were exactly what I needed for the next chapter.
Eventually, I transitioned into insurance claims work—something that was not remotely on my radar back in law school. It turned out to be a career path filled with opportunities for growth, learning, and leadership.
About ten years ago, I left private practice entirely and moved into the insurance industry full-time. From there, my career continued to evolve, and I ultimately moved into leadership, working my way up to lead the Claims department at my current company.
Looking back, the trajectory has not necessarily been as I initially mapped out, but it has been incredibly rewarding. Every unexpected turn has led to new challenges, broader perspectives, and a deeper appreciation for the range of careers a law degree can make possible.
Is there anyone who has had a particularly significant influence on your career? Tell us about them.
I’ve been fortunate to have many influential women in my life, and they have shaped my career in ways both profound and subtle. My first role model was my mother, who graduated from Northwestern Medical School in the 1970s—one of only a handful of women in her class. Her determination, resilience, and belief in her own capabilities set a powerful example long before I fully understood how remarkable her path truly was.
I’ve also been surrounded by entrepreneurial and professional women—friends and colleagues—who are achieving remarkable things in their own fields. Their drive, creativity, and courage continue to inspire me daily. They provide encouragement, perspective, and strength, often at moments when I need it most.
But the people who have influenced my career the most are undoubtedly my daughters. Working parents make countless sacrifices, but one thing has always been non‑negotiable for me: being a visible role model for them. I want them to see firsthand what women can do, the spaces we belong in, and what we are capable of achieving. Now that they are older and understand what I do and why I do it, they have become my biggest supporters.
It is the ultimate reward for me as I listen to them map out their own futures with confidence and intention. I hope the number one thing that I have shown them is that the sky is truly the limit—if I have instilled that mindset, I have succeeded.
How have you grown as an attorney?
When I was a young attorney, most of my energy went into learning the fundamentals—understanding the law, mastering legal writing, and figuring out how to persuade through clear and logical arguments. Those early years were all about developing strong technical skills, and that foundation has served me very well.
As my career has progressed, my focus has shifted. It has become less about how to do the work and more about why the work matters. I now draw on that early training not just to analyze issues, but to think strategically, solve problems creatively, and make decisions that support broader business goals.
Today, my growth is centered around leadership. I work intentionally to be a thoughtful, empathetic leader who listens, collaborates, and creates an environment where people can succeed. One of the most rewarding parts of my role is supporting the professional development of my team—helping them grow their skills, expand their perspectives, and see paths they may not have imagined for themselves.
In many ways, this evaluation and where it has led me is the most meaningful growth of all.
What are you currently reading, watching, or listening to?
I just finished the novel Theo of Golden. It’s beautifully written, but I was moved by the theme of the central character who changes the lives of others through his acts of kindness, and without expectation of anything in return. That kind of quiet goodness is a welcome message and inspiration right now.
As for listening, my 2026 Spotify Wrapped is going to be filled with throwback indie albums from the ’90s. Lately, it’s been all about nostalgia for the soundtrack of my teen years!
What is one thing that people would be surprised to know about you?
This might not necessarily be surprising, but one of the most interesting things about me is my love of travel and how much it has shaped me. I’m so grateful for the opportunities I’ve had to explore and experience countries all over the world. These first hand interactions with people, cultures, and perspectives so different from my own have formed the basis for my values and beliefs. This has also instilled deep feelings of gratitude as I approach the world with curiosity and humility.
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This feature is brought to you by Berkley Select, a proud Sustaining Sponsor of NAWL.