Interview with Karen O’Toole, Senior Vice President and Deputy General Counsel Fidelity Investments

Financial services has long been a vital industry in the Commonwealth, and women lead in that sector as well. Karen O’Toole is Senior Vice President and Deputy General Counsel at Fidelity Investments.  Karen spoke about her career path, the financial services industry, challenges she has faced and what makes her hopeful about the future for women in the law. 

Q: Can you share your path to becoming Senior Vice President and Deputy General Counsel at Fidelity? What experiences, opportunities, or decisions helped shape your path?  

Karen O’Toole: I always liked and have been interested in the financial services industry. After my dad retired from the USAF [U.S. Air Force], he became a broker, and I worked in his office during school and summers. I will date myself, but back in the day as part of my job, sometimes I put paper order tickets into pneumatic tubes to send them to the exchanges. 

I found the US securities markets fascinating. I liked the energy, excitement, connection to world and national events, and helping people invest for their future.  

After law school, I joined a law firm that specialized in securities litigation and enforcement – for example, we handled the defense of class action litigation and DOJ/SEC/FINRA cases. One day the assigning partner asked if I could cover a particular matter. I did and I loved it – it was incredibly interesting and the client that we – I and my firm – represented was doing the right thing by its shareholders. That client was Fidelity. I asked to work on other Fidelity matters, learned the industry and the law, and later was fortunate to have the opportunity to join the Fidelity Legal Department.  

I was a litigator at the time I joined Fidelity, but one of the great things about working at Fidelity is that you can grow professionally and be exposed to many opportunities at the firm. At one point, Fidelity’s General Counsel asked me to work on a new project involving anti-money laundering, which exposed me to new legal and regulatory areas, and I just kept expanding my practice as Fidelity grew into new products and businesses. And now here I am!  

Q: Looking back, what were some of the biggest challenges you faced as a woman in the legal profession, and how did you navigate them?  

Karen O’Toole: As I mentioned, in private practice I focused on securities litigation and enforcement. And at that time, I did not see a lot of women partners in that legal space or even in positions at our clients. I had a lot of adventures, learning the subject area and navigating the practice.   

Once I was in the law firm library and a partner in a different department asked me to pull some books and make copies for him – he thought I was the new librarian! (By the way, we became great friends and he still apologizes to me many years later!) I am sure that many women and others who read this have experienced similar situations. Of course, these kinds of experiences are challenging – they can be demoralizing and can wear us down. But my advice is to keep showing up – take a break, talk to friends and mentors, keep your sense of humor, know that you got this, and advocate for yourselves.  

Q: What’s a lesson you’ve learned over time that continues to shape how you lead and practice?  

Karen O’Toole: I think professional success—in the legal profession or elsewhere—is based on a few key things:  

Your work ethic – Be willing to work hard, help others, learn.
Integrity – Have personal and professional integrity. Do the right thing by your clients and colleagues. 
Be a good person – Be kind to people, respectful, inclusive, collaborative – and work well with people. 
Be smart, inquisitive, and ready to learn. 

In my experience, the keys to success are based on a combination of these things: how you treat people + interpersonal skills + knowledge/brains + hard work and ethics + perseverance.  

A colleague once told me that a happy life is like a three-legged stool: strive for personal  satisfaction (for example, have strong, rewarding relationships with family and friends), professional satisfaction (that is, aim to be happy in your work life), and explore and enjoy other interests (charitable work, fitness, sports, the arts, etc.). I like the idea of balance and strive for it – I do not always achieve it, but I try!  

These are the lessons that I have learned that I try to embrace in my legal career.  

Q: What has been the most interesting or rewarding part of leading within a legal department at a company like Fidelity? 

Karen O’Toole: One big difference between practicing in a law firm and a company is that at a law firm you likely have multiple clients, and in-house you have one client. It is both very interesting and rewarding to be able to deeply learn about and develop an understanding of a client, the way I am fortunate to have been able to do at Fidelity.  

So, for me, it has been interesting and rewarding to immerse myself in the company as it grew. Fidelity has a long legacy of pioneering industry-changing technology aimed at helping our customers achieve their goals. We continue to challenge the status quo and harness innovation to create value for our customers, developing new products and services to stay ahead of their distinct and evolving financial needs.  

Q: What advice would you offer to women attorneys considering or pursuing a career in the financial services industry or in-house? 

Karen O’Toole: I tell women attorneys considering a career in financial services or in-house to look for a firm that is a great fit for you, based on what is important and interesting to you. It was important to me to work at a company that aligned with my values, for example, which emphasizes integrity and puts our customers first.   

I wanted to work at a company where I could stay, put down roots, learn and continue to develop as a lawyer, do challenging legal work, and engage with others in the industry. And Fidelity was the right fit for me.  

I had other in-house opportunities, but the roles were narrower and the career path seemed shorter – I felt I would be managing outside counsel or even more specifically managing outside counsel spend rather than practicing law. That is not what I wanted to do.   

Our in-house lawyers are very hands on – while we work with outside counsel, we are very engaged in our work. We practice law and act as counsel for Fidelity, as we help grow the business and protect the firm. That was important to me.   

Q: What makes you hopeful about the future of the legal profession, particularly for women?  

Karen O’Toole: I am hopeful because I continue to see more women entering the legal profession. And when they do, I see them seeking out opportunities for connections, collaboration, and mentorship, with more senior lawyers, their peers and the next generation. That organic networking is exciting to see and suggests that we are on a path forward.  

In today’s workforce, which spans five generations, Gen Z has the unique opportunity to learn from the women who came before them: adopting what works for them in today’s environment, evolving what doesn’t, and cultivating a more inclusive professional culture in the process.  

We’ve made progress since I started my career years ago, but we have more to do. I look forward to working with the next generation of women lawyers and to watching them make great contributions to our profession!