Pepper Anderson is President and Chief Executive Officer of Chilton Trust, with nearly three decades of experience in financial services and wealth management. Prior to joining Chilton, Anderson spent more than 20 years with J.P. Morgan Private Bank, where she most recently served as Managing Director and Market Manager for Connecticut and Westchester County, NY.

Russ Alan Prince: Let’s begin by having you describe Chilton Trust?

Pepper Anderson: Chilton Trust is an independent, privately-owned wealth management and nationally chartered trust company servicing high-net-worth and ultra-high net worth clients. We are seeking to be a disruptor in the industry by combining the best of traditional, high-touch, and flexible wealth management with today’s technology, access to information, and investment creativity. 

Our firm was founded in 2010 by Richard Lockwood Chilton Jr., who identified a void across the wealth management industry. At Chilton Trust, we combine deep investment expertise with white-glove service to find the middle ground between large brokerage or banks and small trust companies.

As the wealth management industry continues to evolve, Chilton Trust is positioned to adapt to it. We utilize proprietary modeling to build portfolios around our clients, rather than model portfolios that have a tendency to be rigid and overly diversified. In fact, mathematically speaking, you need a lot less diversification in a portfolio than you think. We combine that investing approach with a full suite of family office and fiduciary services to give our clients the benefits of having their own family office without the burden of building and managing all that this entails themselves.

Prince: How are white-glove client services and deepening client relationships instrumental core to your success?

Anderson: The foundation of Chilton Trust is built upon premier client service; we made a commitment to always put the client first and it is one of the main reasons we have been able to find such success within the industry. We think of our network of clients and employees as the “Chilton Trust family,” and within that mentality, our high-touch service is essential to delivering the type of personalized strategies that we offer.  

That grounding allows us to naturally deepen our client relationships. The world of ultra-high-net-worth individuals has a lot of intricacies, and knowing that your advisor is providing you with guidance that’s been crafted specifically for you has a reassuring effect. Over time, the trust that those types of relationships build becomes an invaluable asset that we intend to safeguard as we expand and grow.

Prince: What are your plans for growing Chilton Trust over the next few years?

Anderson: Our growth strategy is a bit different from many of our peers, as we prioritize organic growth. We believe that the best way to gain a new client is through the recommendation of a satisfied client. Taking an organic growth approach allows us to commit ourselves to what makes us truly unique in the industry. 

The fact that Chilton Trust is privately owned, not looking to be sold, and not looking to implement a roll-up strategy or become an acquisition machine shows our clients that we will remain consistent. At the same time, our model has been beneficial for attracting new business given the concern with the industry’s current M&A activity. Our growth approach allows us to stand out amongst our competitors, fosters authentic client relationships, and assures our clients that growth is not our number one priority, they are.  

While the notion of acquiring another firm is never out of the question, it is not a priority and would have to present the right synergistic opportunity that could meet our high criteria. We have explored an expansion strategy, most recently opening an office in Naples, Florida. 

We favor authentic over purely geographic expansion and focus our research on where our existing clients and networks are, rather than on what regions are populated through demographics. We look at markets where we have developed a base and if a firm like ours seems needed, we will happily fill that space. Our new Naples location is a perfect example of this strategy in play as we have many ties to the area and clients who have opened the door for us. As a leader, having this flexibility and open-mindedness has been very empowering, especially as we continue to develop and grow. 

Prince: In September 2020, Chilton Trust received its National Trust charter. How does this allow the firm to continue to provide white-glove client services to clients and has this helped Chilton grow its business? 

Anderson: When Chilton Trust was granted its National Trust charter in 2020, we were the first Trust company to be approved by the Office of the Comptroller of Currency in 13 years. Having this type of accreditation not only is a testament to the quality of our business but is a true value-add for our clients. 

Being granted a National Trust Charter enabled us to expand the breadth of our fiduciary services to our clients on a national scale. We opened our Delaware fiduciary offices in Wilmington, which allowed us to operate within the state’s trust system. For a company that typically deals with multi-generational families, having this flexibility allows us to craft solutions that will help them achieve their goals in the most efficient way possible. We have a brilliant team of fiduciary experts and with this, they can take their level of service to the next level for our clients.  

The fact that we focused our efforts on achieving a National Charter, again speaks to our overall strategy at Chilton Trust. We seek to expand the capabilities of our team so that we can provide the best range of quality services possible, putting the client first rather than prioritizing growth. 

Prince: As we emerge from the pandemic, we have been thrust into the “Great Resignation.” How has this trend impacted the financial advisory space, and what can firms do to help attract and retain talent? 

Anderson: One cannot deny that the talent marketplace has changed dramatically since COVID-19. I believe that what is being deemed the “Great Resignation” is a result of employees feeling increasingly less connected to their employer. For companies that did not already have a tight-knit workplace culture in place, it is difficult to try to build that in a work-from-home environment. 

At the same time, the roles that are available in the financial advisory space are changing. While finance used to offer a clear-cut path for career advancement, today there is a myriad of trajectories one’s career can take because there are so many new types of roles available across the industry. 

As an employer, the challenge is making our positions compelling enough to compete with these new career opportunities, as well as the ones that will be created five to ten years from now. To retain talent, you must think about how a position will fit into the candidate’s career and provide a value-add in ways of development, resources, mentorship, and internal advancement opportunity. 

While wage inflation is one piece of the puzzle, it is also important that employers do not take their employees’ personal and career priorities for granted by focusing on compensation alone. In today’s world, employees take a well-rounded approach to selecting a job; weighing factors like company culture, career advancement, and work-life balance. There are no universal criteria for choosing one job over the next anymore, rather employers must look at the full picture of each person. 

RUSS ALAN PRINCE is the Executive Director of Private Wealth magazine ( and Chief Content Officer for High-Net-Worth Genius ( He consults with family offices, the wealthy, fast-tracking entrepreneurs, and select professionals.