At 25, Vestmark's CEO on outlasting five market cycles — and betting on AI

With 25 years in the industry, financial software services provider Vestmark is emerging as both an industry innovator and a seasoned pro. 

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During the early 2000s dot-com bust, tech upstarts and legends alike succumbed, to the tune of $5 trillion, by some estimates. Vestmark was just getting itself off the ground with tech companies crashing down around it. 

In addition to dot-com woes, over the years, Vestmark has weathered significant financial events, including the Great Recession, the rise of robos, COVID-19, and now, the AI-fueled boom. 

The secret to its growth, according to CEO Karl Roessner, starts with a solid, talented workforce as its foundation. Then, add an unwavering mission to provide great services that meld humans and tech seamlessly to help advisors make smarter, more efficient decisions. 

Where others might shy away from change, Vestmark approaches it head-on. It continues to lean into its SaaS products as a core service, but the addition of Dynasty Financial as a client meant taking on new challenges.

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"Dynasty was our first break into the RIA aggregator market," he said. 

To better service its clients, Vestmark also launched a tax tool suite called VAST. Introducing VAST also provided an entry point for more RIAs to use Vestmark products "without having to convert off an existing platform," he said. In addition, Vestmark introduced Pulse, a real-time information hub that utilizes AI agentic loop technology. 

Roessner, who just marked his fourth year at the company, took a quick look back, shared what's going on right now and a bit about the company's planned way forward. 

This interview has been lightly edited for clarity and length. 

Karl Roessner Headshot.jpg
Anthony Tulliani/Anthony Tulliani

Financial Planning: You recently reported exponential growth to $50 billion over the past handful of months. Congratulations!

Karl Roessner: Vestmark was built by intelligent, hardworking individuals, many of whom are still here today. So we do have the 18-to-24-year tenured employees, and they've really kept this place [going]. They love to innovate, to continue to deliver products and to make customers happy. So that's how this place survived and thrived for 25-plus years. 

The core group has fostered that spirit of innovation, and in the past four years we've been able to tap into that, add some new people, deliver some new products and really grow the company in a meaningful way. It's been an amazing journey. We look forward to what we do every day.

FP: You've reported that the growth is related to branching out into the RIA space. Tell us about tech solutions there.

KR: We have to provide a solution that is really simple, or at least intuitive, for the advisor to use, because our job is to make their lives easier every day.

Our newer RIA partners have been fantastic. Our technology is leading edge with UMA technology that we can deliver for them, but it's also about the stability, reliability and the compliance, alongside the safety of the underlying tech. 

FP: What are some of the lessons around working with RIAs more?

KR: The key is listening to the customer or potential customer because you don't want to walk in with guns blazing or over-technical speak and tell them how great your mousetrap is. The real way to build a partnership is through communication and listening, and sometimes it can be a very long sales cycle, because at the end of the day, it comes down to trust. 

Do they trust you to help them with their clients? Do they trust that you're going to be there every day for them? So we do go in and have some great technology, and the user experience is very simple, but it's really starting with those basic building blocks of listening to the customer.  

FP: And what about introducing new tech to a client?

KR: You don't want to overwhelm, and you want to try and make sure the solution fits their needs. The technology for VAST is extremely simple. Once we get in front of the advisor, we can point them to a URL and say, "Take a look for yourself." It asks some very basic questions about the portfolio, and they're off in terms of building a proposal almost immediately. 

On the SaaS side where we're delivering our rebalancing technology, that's a longer sales cycle. That's looking at a growing company and letting them know how a system can help them continue to grow. We take them through the demos and walk down that path. It's a lot of fun getting to know people and understanding where they're going, and taking the right path for the client.

READ MORE: 2 AI platforms tackle the headaches of client, advisor moves 

FP: Tell us about the role AI plays. 

KR: We've been implementing and using AI tools for almost three years now and use it in different ways. First and foremost, in our own internal workflows, every employee has access to and has been trained in Claude Code, so they're either using it or Cowork in their daily lives, and we hold regular training programs for all employees. On the technology side, we've seen a 65% productivity improvement in folks who have adopted and use it regularly, so it's been a great uplift. For process flows, we've implemented AI, and use agents to help with standardized processes and workflows. 

FP: And what about the Pulse component?

KR: Harnessing that agentic loop technology can be extremely powerful in terms of giving the advisor a dashboard they can use every day. So, scraping all of the news that's available, taking a look at what's happening in the markets, and then looking at the portfolios, and flashing up a screen that basically says, "this is what's happening in the Smith account. You may want to call Mrs. Smith and let her know," or "Mrs. Smith's portfolio has traded far away from the model. You may want to do a rebalance. Here's how to do a rebalance." 

FP: What are some guardrails you keep in place? 

KR: We do not expose client data or anything that would be damaging or harmful. It's all built on our core technology, so it's all internal. We're not sharing any data with the large language models or sharing it out to any of the large language model providers. So it's all within the four walls of Vestmark. That's one of the key things that we've done. 

We're also very good about monitoring through all available devices and technology. We monitor the way our employees use AI to make sure no one's doing that magical fat finger that ends up costing companies reputation and trust. Nobody wants that. So, we are very careful and thoughtful about that, because the customer relationship is about service, scalability and how great our products are, but at the end of the day, it's about trust. They trust us with their clients' data and information on a regular basis, and we owe it to them to safeguard that in every way possible. 

FP: Share a guardrail-specific challenge.

KR: One thing for me is the tech where they can present as being you. That's the hardest part when they take over that individual, and that takes a lot of training and help for the employee base to protect them from having that happen.

FP: What's next?

KR: Continue to take care of and service our core customer base and service our larger customers, and then continue to deliver a product set into that growing RIA aggregator marketplace. That space is evolving very quickly, the tech is moving very quickly and that's where we'll continue to deliver. We'll continue to refine and grow our advisor suite of products, and to deliver more AI-native products out into the marketplace. We have our first products out there, with two or three more coming by the end of this year.


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