On March 20, 2025, the CFA Society Chicago hosted a Distinguished Speaker Series (DSS) event presented by the DSS Advisory Group. The event featured a conversation with Heather Brilliant, CFA, Chief Executive Officer of Diamond Hill, a valuation-disciplined boutique asset manager based in Columbus, OH. Rachel Madsen, CFA, Director of Institutional Strategy and Development at Loomis Sayles, moderated the conversation.
The event started with welcome remarks from Chris Vincent, CFA, President & Chief Executive Officer of CFA Society Chicago. Chris highlighted that CFA Society Chicago is celebrating its 100th year in 2025 and will also be the host of CFA Institute LIVE 2025 beginning on May 4 this year. Vincent also highlighted Brilliant’s notable service to CFA Society Chicago and the overall CFA Institute, having served on the boards of both organizations over the years.
Madsen initiated the conversation with Brilliant by noting the many industry trends that continue to be in the headlines since Brilliant has last been part of the Distinguished Speaker Series, including fee compression and the rise of artificial intelligence, and asked if those trends were impacting how Brilliant was managing her company now. Brilliant noted that some of the recent downturns in the equity markets seem to signal some sense of a return to rationality given how markets could be perceived as overvalued in recent years. Brilliant noted that value investing philosophies have been enduring a long run of extended valuations in recent years. Brilliant also pointed out that the recent equity market downturns have highlighted opportunities in fixed-income investing, as some fixed-income securities are seeing strong real returns.
Madsen inquired into Brilliant’s initial attraction to the investment world, and Brilliant noted that she initially had full intentions of going to law school, but then, during her undergraduate years, switched from a major in political science to economics and was very intrigued by her classes in international finance. She wanted to work some before a potential return to graduate school and was hired by Bank of America in 1998. Brilliant noted some key transitions in her early career helped shape her ongoing interest in investments. She started out as an equity analyst for 10 years but noted she was not confident that this career was her true calling. She noted to the audience that making sure others know about your desire to move into new roles can be valuable as not all future available roles are formally posted at firms. At Morningstar, she moved up through the ranks, eventually managing around one hundred people in a cost-center role. She later moved into broader leadership roles, fulfilling her ambition to have P&L responsibilities. Her final position at Morningstar was to serve as the CEO of Morningstar Australia / New Zealand.
Madsen asked about Brilliant’s transition to Diamond Hill and what she found to be challenges and interests as Brilliant started her role there. Brilliant noted that she was Diamond Hill’s first external appointment as CEO, so she was focused during her initial time
there on continuing the firm’s portfolio mentality and helping the team gain familiarity with her style. In the past, the company had tended to have investors as CEOs, and in her role, she wanted to emphasize strong leadership qualities. She initially noted some hesitation in moving to Columbus, Ohio, but has found that it is a great and growing city and quickly got involved in the broader Columbus community. She appreciated that Diamond Hill had historically had strong client relationships and wanted to continue emphasizing that with the firm.
Brilliant noted that two of the core values that she emphasized the most in her work were humility and vulnerability. In her leadership, she tries to apply broad leadership skills and then applies humility. At times, she admits that she may not know the final answer but looks to work towards a collaborative solution. She emphasized that strong leaders could show vulnerability by admitting that there are challenges, and being transparent and emphasizing a well-thought-out group conclusion can be beneficial.
Brilliant also noted that each organization is different when it comes to creating and implementing strategies. She has found a lot of value over the years in collecting small group insights, understanding the culture of her organization, and emphasizing where her firm may have a competitive advantage. She noted it was important to her to be able to articulate the firm’s values and build them further through employee involvement. She noted that Diamond Hill has always been long-term oriented in its investment analysis and has a deep understanding of what drives the cash flows of its investments.
Madsen inquired if there were any key strategic changes that Brilliant saw as important as she moved into the role at Diamond Hill. Brilliant noted that the firm had historically been focused on U.S. equity and, when she came into the role, was generally 99% focused on that investment category. Since then, she has been emphasizing diversifying the business, leaning more toward fixed income, and contemplating building up more of an international equity franchise in the future. Additionally, Brilliant noted that the role of growth at the firm had been a key discussion. Internally, the firm had debated whether overall growth was important and whether the firm could focus simply on staying at a similar size and serving the current client base. Brilliant pivoted the firm to move towards more growth, noting that it was not inspiring to not grow and would provide the best future opportunities for their employees and clients.
Brilliant added that her arrival at the firm was just in advance of the global COVID pandemic in 2020, and many early decisions were entrusted to her as the new firm leader. She noted that her early efforts in getting to know and trust key people within the firm were key to making decisions early in the pandemic. She recalled some early decisions on the key day of Friday, March 13, 2020, when they needed to come up with a defined remote work plan that she knew would have to work at least for the next few weeks and might have to be the way the firm ran for the next few months. She made the decision to send
people home with a wide variety of company assets such as desktops, laptops, monitors, and technology to get work done and stay connected. The firm has approximately 130 people, and she flexed to create some leadership through various video messages and town hall meetings. She again noted there was some vulnerability in these activities since she herself thrived on being in person to collaborate and do great work for their clients, and her staff was relieved to hear her make these vocalizations in order to stay in tune and stay real with the way the pandemic was evolving.
Brilliant added that a key asset of leaders was to be able to address change and build strong communication. She focuses on meeting with employees both individually and within small group settings, which can help substantially when change occurs within the organization. Brilliant also emphasized that culture is an important part of running an organization. A firm’s culture can be defined at times by identifying the worst behaviors that are tolerated, and strong leadership will look to have zero tolerance for adverse behaviors. She noted that being “Midwest Nice” can lead times to inadvertently accepting behaviors that firms might want to avoid but do not get appropriately addressed.
Finally, Madsen inquired to Brilliant about her thoughts about women in leadership in the spirit of March as Women’s History Month. Brilliant noted that the proportion of women in CEO roles is still low, and additionally, there is still an underrepresentation of minorities. Madsen noted that current events in the U.S. have been leading companies to reassess their position on diversity, and Brilliant added that Diamond Hill has ongoing efforts through their foundation to help encourage organizations who focus on moving the needle for broader diversity within the investment profession and noted that there is a strong benefit to have diverse and inclusive teams.
A question from the audience asked for thoughts on the future of mutual funds. Brilliant does not expect mutual funds to grow further but predicted that they will not completely disappear. In contrast to mutual funds, Brilliant noted the growth of exchange-traded funds (ETFs), as well as that of other investments vehicles such as Collective Investment Trusts (CITs) and separate accounts.
The event concluded with thanks to Brilliant and Madsen for a great discussion and helpful insights on leadership within the investment profession.