From legal work to digital asset management strategy: A conversation with Cynthia Lo Bessette, the head of Fidelity Digital Asset Management

In this next episode of The Heidrick & Struggles Leadership Podcast, Heidrick & Struggles’ Lee Hanson speaks to Cynthia Lo Bessette, the head of Fidelity Digital Asset Management, about her journey from starting as a young lawyer to leading digital asset investments and solutions at Fidelity. Lo Bessette shares the skills and capabilities that helped her make the transition, as well as her insights into people management, building and managing diverse teams, and fostering innovation and engagement. Finally, she shares her advice to other legal leaders who might have aspirations to move into a business role.

Below is a full transcript of the episode, which has been lightly edited for clarity. 

Welcome to The Heidrick & Struggles Leadership Podcast. Heidrick is the premier global provider of senior-level executive search and leadership consulting services. Diversity and inclusion, leading through tumultuous times, and building thriving teams and organizations are among the core issues we talk with leaders about every day, including in our podcasts. Thank you for joining the conversation.

Lee Hanson: Hi, I'm Lee Hanson, vice chair and partner in Heidrick & Struggles’ New York and San Francisco offices, and a member of the CEO and Board of Directors and Legal, Risk, Compliance & Government Affairs practices. In today's podcast, I'm delighted to be joined by Cynthia Lo Bessette, the head of Fidelity's digital asset management division, where she has oversight and responsibility for setting the strategy and priorities for the division in building digital asset investment capabilities and solutions for Fidelity clients and investors across the company's platforms.

Cynthia leads the teams responsible for the development of the digital asset research and data platforms and research agenda, including evaluation of blockchain protocols, infrastructure, and financial applications. In addition, she leads the teams responsible for the development, implementation, and ongoing management of digital asset investments, products, and solutions. Previously, she held roles as chief legal officer for asset management and head of digital assets legal at Fidelity. 

And, I'll add, I've known Cynthia now for a dozen years or so and very delighted that she's agreed to speak with us today. Thank you so much, Cynthia. 

Cynthia Lo Bessette: Thank you so much for this opportunity. 

Lee Hanson: To start us off, could you please tell us a little about your career journey from starting as a young lawyer to where you are today? What skills or capabilities from your legal work were most helpful to you in making the move? 

Cynthia Lo Bessette: Sure. I started out in a very large law firm, like many young lawyers coming out of law school, and within my role as a first-year associate in the law firm, I got to work on a number of really interesting projects across a range of different business lines and types of work as well. 

One of the things that I found pretty consistently in all the different projects that I worked on, as well as with many of the senior lawyers that I worked with, was the importance of asking questions: asking lots of questions not just around what the project was about but, more importantly, the objective and the purpose of what the clients were looking to achieve.

Whether that was working on a very large litigation project and understanding what the nature of the dispute was, or whether that was working on the setup and launch of a new hedge fund—there's definitely a range of projects that I worked across!—and understanding the client's objectives, I was asking a lot of questions about what business the client is in. 

I had tremendous teachers and mentors across the firm who had the patience and the time to answer all those questions was just a huge benefit as a young lawyer starting out. 

Lee Hanson: You know, you've had a long career in the investment management space. I think we met when you were still working at Oppenheimer. What attracted you to that sector originally, and what were the significant changes you've seen over the years in the industry? 

Cynthia Lo Bessette: This is an area of the investment and financial services ecosystem that's gone through a lot of change. Starting out as a young lawyer, working on the setup of private funds was my early introduction, and it really resonated with me on a number of fronts.

I started out in undergrad and graduated with a degree in East Asian studies and economics. So, the whole idea of being able to set up funds that were investing across capital markets and thinking about capital allocation and access to financial services started early in my career. Certainly to me, it resonated with a lot of what I spent many years studying.

And so, the opportunity to be able to build products to help investors to meet their financial lives really just was so interesting. After a few years of working in the big law firm, I took my experience and was able to find an opportunity in-house working for one of the largest asset managers at the time. 

As a young lawyer going into a well experienced and very tenured large in-house department, I also got an opportunity to work on a range of different business lines within that asset manager, starting from retail mutual funds to a few of their non-US business units, setting up funds, and also working on investment products in non-US jurisdictions. So, I got an early introduction to a range of different investment type vehicles. I was working with really high-quality people as we were developing new products or opening up new markets for the business that we were in. 

So, as I think back and look at the industry over the last few decades, there's definitely been a few themes, one of which is consolidation. There's been a lot of M&A activity across the asset management industry. I do think that the innovation across products and structures to be able to deliver investment experiences has also really proliferated in this space. And I think that's to the betterment of investors: getting better access and more cost-efficient access to investment products to help them manage their financial lives.

Lee Hanson: You joined Fidelity after spending several years at Oppenheimer when the company was sold to Invesco. What are the differences you've experienced when you stepped into that role from either a company, culture, or business model? Anything else that you would point to that was different? 

Cynthia Lo Bessette: So, carrying forward the theme of M&A in the asset management industry: it, on the one hand, certainly creates efficiencies and scale for asset managers, but it also creates interesting opportunities. The opportunity to join Fidelity certainly was very interesting and Fidelity certainly has a reputation across the industry as being a leading innovator of financial services. 

One of the things that I don't think I fully appreciated until I started here was really the value of the breadth of the businesses that are part of the overall Fidelity portfolio and enterprise. Fidelity has this really unique combination of both distribution businesses covering a wide range of client needs in their financial lives, and of course world-class asset management business that's here. It's just an incredible privilege to be part of this group as we are continuing to look at ways to develop innovative products and services for our clients.

Lee Hanson: You inherited a pretty sizable team as head of asset management legal when you came to Fidelity. What were the challenges you faced stepping into that role, both from a learning curve, people management point of view? 

Cynthia Lo Bessette: So yes, there is an incredibly talented team of in-house lawyers here within the asset management unit.

You know, one of the things that was very evident to me in the early days was just how diverse this team is, in terms of their experience. There are quite a few lawyers who have spent a very long portion of their careers here within the asset management legal division, and several of them have had quite a wide range of responsibilities. I think that again represents the breadth and the scope of the asset management business here. The talent certainly is very deep. 

The challenge for us as an organization has been to continue pushing forward on innovation and growth in this industry, which means adding new products and structures to the overall portfolio that we offer. The culture here is incredibly collaborative and very much relationship based, and it is so evident to see all of the longstanding relationships not just within the legal division, but across the business—how well the teams all work together, collaborating. 

Lee Hanson: What I find interesting is you actually created a digital assets team in 2022, prior to your current role leading the business. Can you talk us through that journey? How it came about and what drew you to a business leadership role? As you know, that's not common in legal departments. What have been the challenges in rewiring your focus, and how do you spend your time differently than in your prior role?

Cynthia Lo Bessette: So, the digital asset business is something that came out of many years of research and development in the digital asset, blockchain, and crypto space, starting back for Fidelity in 2014. 

When I joined in the summer of 2019, I had the opportunity to get to know the digital asset team. Some of the early work where they were looking for some support was building digital asset investment products. And so, there was a natural synergy between the legal support that we were building for our alternative investment business and taking on the support for the digital asset team as they were looking to build investment products. 

That support continued to grow and my own personal interest in crypto was piqued as we were building investment products that gave our customers and our investors the ability to be able to access crypto and digital assets. And, speaking from my economics background, the promise of the blockchain technology and what we think the long-term impact is going to be on the way that our capital markets and financial services will function is rather profound. Thinking about the impact that this technology will have on the way that we're able to transact and store value and offer financial services in the future really was very interesting and was something that I wanted to learn more about.

There really was no better place to be able to have access to expertise and a number of individuals across this organization who were very patient. We spent quite a long time talking about the ways we could leverage this technology to improve the way our products could be delivered, or the way we may be able to build financial solutions, and I think that really was what drew my interest. 

And then, of course, providing the legal support was a natural extension of the team that I was leading. I think at some point, it just became much more relevant to take the group of lawyers who were working on digital asset products and put them together in a team environment where they could work together and share their insights and their perspectives. This was an area where the regulatory environment was evolving and the technology was continuing to evolve, and having the benefit of internal sharing of information and insights in a team environment made a tremendous amount of sense.

Lee Hanson: It’s a terrific opportunity, and not one that many general counsels have an opportunity to do. In terms of motivating your team, have you found that business people respond differently than lawyers? Anything that has surprised you or things you've had to learn? 

Cynthia Lo Bessette: Well, I think, you know, at the end of the day, people are people, whatever your functional role is in the organization.

I think in my role as the head of legal in a couple of different organizations now, I have found that from a leadership standpoint, you need to focus on being able to provide a clear vision for the team. If that is a team of lawyers, that vision is, largely going to be driven by the objectives of our business partners. 

Now, sitting in the role as the head of a business, providing that clarity and that vision is about asking how we grow the business, such that we are delivering high quality and relevant products and services to our clients. How are we continuing to scale that business so that we can continue to grow in that opportunity to be able to provide services to our clients?

Alignment for the team is another important element of running a team, whether it's a team of lawyers or a team of business people. It is about ensuring that everybody on the team understands how their contributions continue to further that vision and that mission. 

I think it's also incredibly important to acknowledge the contributions and to express how much the value of those contributions matter for our ability to be able to deliver on our business objectives. So, there's a lot of synergy between the two leadership roles. 

Lee Hanson: One last question I have for you, because we often meet with general counsels who are very accomplished in their own roles and have an interest in moving to the business: what advice would you have for them, if they have aspirations to move into a business role?

What are the warnings, what are the challenges? And are there any character traits which you believe make some lawyers more successful than others at making that transition? 

Cynthia Lo Bessette: The first thing I always say to anybody who is asking about career advice and the most important bit of advice that I've ever gotten around career objectives is to boil it down to what about your job and your day-to-day work gives you joy. You should be seeking roles that give you joy. And I think being the head of a legal division, or being the head of the general counsel of a company, or being the head of a business unit, you have to ask yourself: what are the elements of those roles that give you joy? 

And for me, working in-house, I've always found joy in being able to be a great partner to my business partners. A big part of that is aligning all of my goals and objectives to help further and enable the success of the business overall. When I think about this opportunity now, to be able to lead a division within the organization, it's such an incredible privilege to be able to set that vision and objective, to help to bring along a group of people that we think are creating interesting, innovative products, and to be able to deliver on that value to our customers.

Being able to do that certainly sparks joy in the team here, and sparks joy in me—being able to do this work and be able to build new, innovative products with this just incredible technology. 

Lee Hanson: Well, congratulations again for making this transition so successfully, and thank you very much for participating in this podcast. I really appreciate it. 

Cynthia Lo Bessette: Thank you again for the invitation to be on the podcast. I really enjoyed the conversation today as well.

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About the interviewer

Lee Hanson (lhanson@heidrick.com) is a vice chair and partner in Heidrick & Struggles’ New York and San Francisco offices and a member of the CEO & Board of Directors and Legal, Risk, Compliance & Government Affairs practices.