Breaking the Mold: Q&A with Freedom Dumlao, Chief Technology Officer

A year after joining Vestmark in October of 2024, Freedom has had an opportunity to find his groove at the firm, which offers software solutions used by wealth managers, RIAs, financial advisors and asset managers. Catching up with Freedom recently, he shared his thoughts on artificial intelligence in finance, his philosophy on being creative in a regulated industry, and how “diversity of thought” can make a team stronger.

Five Questions with Freedom Dumlao 

Your resume shows a lot of interesting experience, but this is your first job in fintech. What was your journey to Vestmark like? 

Ultimately, I am a maker. I love to build and make things – I do a lot of carpentry and cooking, but I really love building in code. With software, you can invent something and see it come to life immediately. I started young, learning to code on a Panasonic JR-200U computer my mom won. I didn’t even know I was programming, I just loved doing it. Since then, I’ve worked everywhere from start-ups to large companies. I spent time at LogMeIn, then at Amazon where I worked on Alexa, and later Zipcar and Flexcar. I found my way to Vestmark through people who convinced me fintech was not as boring as I had feared. What I found here were people who want to be transformative. That’s what I love to do and coming from outside the financial world I can bring perspectives that help push the envelope. Others here have that finance mindset and help make sure we meet the needs of that market. It takes both viewpoints to make sure we live up to Vestmark’s legacy as both a trusted partner and an innovator. 

What is the biggest revelation you have had about fintech since joining Vestmark? 

I’ve learned that development in fintech doesn’t have to be slow. There is this general belief that because we work in a regulated space, because people tend to be conservative about money, that innovation and development need to be slow. I think it’s a self-perpetuating belief. We’ve proven it doesn’t have to be true. By applying best practices from other tech firms and startups – even though Vestmark is more than two decades old, we try to think like a startup when it comes to tech development – we’ve increased speed without adding risk. It’s just about knowing where the guardrails are and respecting them, but if you do that right, it doesn’t need to slow you down. 

How do you innovate within a regulated industry? 

Regulations are only one of the things that can block innovation. There’s a theory about how you recognize and approach barriers to innovation. It starts with your own willpower, what you accept as the boundaries of what you can do. The second stage is the contracts you put in place – essentially, what you and your clients agree you want to do together. Only after that comes the regulations, and you adapt to work within them. By starting with a sky’s-the-limit mindset, and getting customers to buy into that, and then tailoring to regulations, you can get much further than if you start by focusing on limitations and deliberately build to meet them. 

Is it easy to get customers to join you on that journey? 

It’s partly about finding customers with the right mindset. If they want to be innovative in what they do, we can support that. It comes from another revelation I’ve had: It seems like every one of our clients is doing the same thing a different way. They have similar issues, but their own history and growth led them to very different approaches. So Vestmark has lots of experience with creative problem solving. Our software has essentially been co-developed with our clients. The result is we have this toolkit to address so many different challenges and approaches. If our clients are willing to let us innovate with them, we have proven solutions in place that they can use in new ways. 

AI is one of the hottest topics in wealth management and finance. What is one observation you have about AI? 

The most interesting thing I’ve been thinking about is how it affects front-line financial workers. AI is making financial advisors the new doctors – people come to them with ideas they are getting from AI, just like patients come to doctors with internet research, and the advisors have to react to that. It’s going to take a different kind of training for advisors, and a better understanding of what AI does well when it comes to finance and what it doesn’t. I’m going to hopefully be doing more thinking and writing on that topic in the months to come.