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Episode Transcript
Craig: I’m excited to introduce our next guest. It’s Raakhee Miller, President of Siebert Technologies. Raakhee, thanks for being here.
Raakhee: Hi, thank you for having me.
Craig: It’s a pleasure, especially this time of year, to talk to people on the holidays. How are your holidays going?
Raakhee: Great. Made a good turkey, so that’s always good.
Craig: Nice, my favorite. I’m still eating stuffing.
Raakhee: I’m a big stuffing fan, so I like extra stuffing. I’ll be eating it for days.
Craig: I’m still doing it. Excellent. And where are you calling from, Raakhee?
Raakhee: From New York. We’re so close.
Craig: I’m in New Jersey. We should have done this in person.
Raakhee: Next time.
Craig: Next time, we’re going to meet and do it in person. But since we’re apart and on Zoom, why don’t we jump in and give us the 30-second elevator pitch for Siebert Financial?
The Heritage and Business Pillars of Siebert Financial
Raakhee: Siebert Financial is one of the pioneering legacy firms in U.S. finance. It was founded by Muriel Siebert, whose name we honor, and she was the first woman to own a seat on the New York Stock Exchange back in 1967. We’ve been a member of NYSE longer than any discount broker in operation today. That’s a milestone for us. We operate on a couple of core pillars, our business lines, including retail brokerage, wealth management, which we also call Siebert Next, and our corporate services business, which includes equity compensation, plan administration, and other corporate services around those needs. As a president of technology, I oversee the entire tech ecosystem that powers each of those business lines from the client-facing platforms down to our trading infrastructure. We’ve recently added Siebert Pro, which is our infrastructure for professional traders, which is a exciting project that I started and have launched in my tenure here at Siebert.
Craig: That’s excellent. And just, you find a little bit of background on Muriel Siebert, but when I was coming into the industry, she was still a big name. I happened to do some research on her back in the day and was very impressed. At that time, it was unheard of for a woman to even be on the floor of the exchange. I’ve worked on multiple exchanges as an intern growing up. You never saw a woman on the floor, except maybe as a secretary. Seeing a woman who had her own firm was groundbreaking. She paved her own way.
Raakhee: We all ride on the shoulders of giants, as they say.
Craig: We all do, exactly. I think more people should know about her and just do a little reading on her. She passed away about 10 years ago. But she was awesome. Let’s talk about your tech stack, because this is a tech podcast. Can you give us a quick overview of the main systems you guys are using?
Raakhee: We have a combination of homegrown and vendor systems. Primarily, we have all of our client-facing technologies that we own and run. Essentially, our services architecture incorporates a hybrid of vendor and homegrown services. We are looking more and more at the cloud. A lot of our core services run on the cloud. On the back end, we do have some key vendors that we still use.
Craig: Excellent. We’re always seeing, we talked a lot of RIAs. Of course, it’s a constant process of modernization. When you’re successful, like a firm like Siebert is, by definition, your technology is going to become legacy because you’ve been around a while and it just starts to get older and it’s in the inertia. What was the original push for this round of modernization of your tech stack?
Modernization as an Existential Necessity
Raakhee: At this stage of where technology and innovation is, modernization is not just an attractive buzzword. It is existential. Firstly, the client expectations have fundamentally shifted. Everyone’s expecting real-time everything, instant account opening, immediate funding, execution visibility, metrics, mobile-first experiences. Our legacy infrastructure and a lot of firms of our tenure have infrastructure that was built when the world was still T plus 2 settlement. That’s moving fast. Secondly, the competitive landscape forces our hand and it has intensified. Certainly more dramatically as the years have passed, fintechs have come in over the last decade and unbundled what have been traditional broker services, call it Robinhood or others in this sphere. Now we’re not just competing on price, it’s a race to the bottom. We need technology as a lever to improve and maintain quality. Relying on legacy systems alone will not cut it. Third is a phrase I’m sure that most of your listeners will be very familiar with is tech debt. It becomes a compounding liability every year. When you have systems that don’t talk to each other, manual processes that create ops risk, a patch quilt of vendors and relationships that you need to manage, the status quo of maintaining that becomes higher and higher. At the end of the day, the cost of keeping status quo, when that becomes more than the cost of doing the transformation, that’s when you start seeing the acceleration to that. Finally, we have a brand heritage. As you pointed out with Muriel Siebert, she did something nobody even heard of. We, right now, as part of our fabric, are focused on democratizing finance, and we want to be the pioneers for people and their access to wealth management. Without technology innovation, our messaging, our brand, what we stand for, will be undermined. We have to come together to make this work with the newer technology.
Craig: You mentioned how a lot of the tech stacks were built during T plus 2, which seems a long time ago, but it was just 2017 when T plus 2 came out. People don’t realize the original SEC settlement cycle was five business days.
Raakhee: Can you imagine? Five.
Craig: Can you imagine that? Imagine waiting for a settlement. Then I think T plus 3 came out in 1993. So it’s already 30 plus years ago that we had T plus 3 as the rule for 25 years. Now T plus 2 in 2017, now T plus 1, just 7 years later. Our cycles are getting increasingly faster in increasingly shorter amounts of time. That puts a lot of pressure on.
Raakhee: Absolutely. And it’s going hand-in-hand with customers’ expectations of, I did a trade, I want to see my money in my account. You throw in blockchain and other innovations of the last decade, and these are all possibilities right now.
Craig: Money transfer. When I do a transfer, I want the money in my account the next day.
Raakhee: Exactly. Why not same day?
Craig: I can do it with Bitcoin, it takes 10 minutes. Why can’t I get my cash out of my account the same day, which is impossible. But hopefully soon, T plus 0. That’s the next step.
Raakhee: All right.
Craig: We talked about strategy, we talked about history, we talked about your tech stack. Everyone’s got similar roles. Every firm, we’re all doing the same thing here, but we have to differentiate. When it comes to the technology side on Siebert, how does it differentiate from your competitors?
Implementing a Composable and AI-Embedded Architecture
Raakhee: I think the goals sometimes are not as differentiated, because people have similar goals. We’re focused on more of a composable architecture. For the longest time, many tech leaders have been focused on moving to API first, services-based modular architecture instead of monolithic systems, building out services that can be assembled and reconfigured and scaled independently. In that particular strategy, I don’t think we’re alone or differentiated, but I think it’s our approach to it at this point. We are leveraging, AI isn’t a bolt-on, we’re embedding it into our architecture as we’re attempting to build out these things, whether it’s in our design and UX cycles, whether it’s in our test development and entire SDLC cycle. We’re also focused on data-driven first. The keyword is intelligence, which means the data that we treat it as a first class asset. Every interaction, every transaction, every client behavior is a signal. We’re focused on building our architecture to capture, unify, and activate our data and have that be a driver for our roadmap and for our architecture needs, as well as operational efficiency. That’s an approach-oriented differentiator, whereas the goals for many organizations are the same. They’re still doing things the same way that they were doing them 10 years ago, 6 years, 5 years ago.
Raakhee: The world 5 years ago and now is completely different, and that gap keeps climbing higher and higher. Finally, we are more focused on human augmentation. Unlike pure robo-advisors or fully self-directed platforms, our bet is that the future is going to be more hybrid, where tech amplifies our advisors, our clients, our service providers, but at the core of it, we are still focused on relationship building and nuanced advice and complex problem solving. We want to automate away the repetitive, the transactional, and we want to focus on personalization. When I look at some of our peers and what they’re doing, there’s a lot of focus on modernizing front-end, while the back-end remains fragmented, hamster behind the wheel. We are focused on modernizing end-to-end. A beautiful mobile app that’s still connected to a system that was built in the 1980s and runs on the mainframe, that’s not going to last. We’re focused on end-to-end, all our processes, and ensuring that the way in which we are approaching these end goals of modularity or data intelligence or AI is embedded into our process.
Craig: You said a couple of things I wanted to call out. One, you said you’re treating your data as a first-class asset. Love to hear that. We did a series of webinars last year on data, which we call data as an asset.
Raakhee: A lot of firms don’t realize that.
Craig: They don’t think of it. They just think of it as plumbing. We just need the data. That’s it. We don’t think of it as something we should leverage. How do we generate more revenue on it? How do we be more efficient with it? I love to hear that it’s an asset. You mentioned something else. You talked about composable architecture. Could you maybe expand on that a little bit?
Raakhee: Composable, modular, the ability to take a process or a problem set and break it down into parts that could be leveraged. Whether it’s certain types of calculations, certain type of data handling, certain type of exception management, we are looking at how to, if you think about in more object-oriented, I’m geeking out on real basic stuff here.
Craig: That’s what this is about. We’re a tech podcast.
Raakhee: What are the objects that run our business? It’s thinking about it at a high level and then implementing that high level concept at the most granular level. It’s not achievable for everything because there’s a cost of overanalyzing and not getting to market fast enough. But there is enough in the in-between for us to think about how can certain services be thought of as reusable, composable activities that can be reused in different parts of our business, different workflows.
Craig: I want to talk about your role. You’ve been at Siebert for not quite 2 years, and you’ve got a great resume. You were over a decade at Goldman, some time at Morgan Stanley. How did that experience, you were working in derivative operations, prime brokerage, equity swaps, so that’s different from the role you’re in now, but clearly a high pressure environment, high expectations for everyone. How did that shape and change the way you approach this job?
Raakhee: I go back to the simplicity of where’s the friction that drives where the client pain is, and it’s always been working backwards. The friction is either in some kind of operational cost or risk or client pain, unhappiness. The goal has always been across all of these roles to seek out that problem, prioritize it well, which sounds simple, but in a large, complex organization with many layers and political things going on, it can be a skill that makes or breaks most tech professionals. At the end of it, it’s articulating and finding data that supports your argument around where the frictions are, where the pain point is, and then working backwards to that. For most parts, if that process is done in a robust manner, and there is organizational support, which generally comes when you have data and good information to present to your stakeholders, you’re then given mandates to fix the problem. What happens magically when you fix these problems, they don’t exist anymore and things get easier or better or less risky. Clients are generally happier and those all, in the long run, contribute to the ROIs. That’s the flywheel effect at that point and you do more, you see more benefits.
Craig: Sometimes fixing the problems only expose more problems and the clients aren’t happy because they go, oh, I didn’t realize that’s fixed, what about this?
Raakhee: That’s a risk, but also a ticking time bomb because if you don’t focus on fixing it, then it might come and manifest in a time that is going to cost you regulatory issues or bigger client issues.
Craig: I wasn’t saying don’t fix it, but I’m saying that sometimes your clients, whether they’re internal or external, are never happy.
Raakhee: That is true. The business always wants it yesterday and the clients are never happy. But there’s a relative sense here. As long as your services are giving them the value, I think the value matters more than issues at certain points.
Craig: Hopefully. Let me ask you a question that I get asked a lot. How do you decide, you mentioned your tech stack has a mix of in-house developed applications and off-the-shelf products. How do you decide which capabilities to build in-house versus buying or renting from a vendor?
Strategic Framework for Build vs. Buy Decisions
Raakhee: Mainly it’s three core questions. First is, is this capability core to our competitive competency? If it’s something that we believe clients choose us for, it’s important to know your identity. We are a retail brokerage, we have our wealth management, so we want to focus on knowing our clients. If something is a core competitive capability of ours, we want to own it. We want to build it in-house, or we want to acquire. A lot of our client experience layers, our advisor tools, and our data intelligence, that’s ours to own. That gives us the most roadway to improve, further excel, extend the gap between us and our competitors, and to underscore the value that we’re providing our customers.
Raakhee: The second is if it’s a commodity. Market data feeds or basic order routing or standard compliance reports. These are commodities. Vendors have the type of scales and economics that we can’t match. We’re not trying to build that. If we do our jobs right, eventually we’ll become a vendor and pitch these services back out to the market. But we’re not in that business right now. We want to rent commodities and make sure they’re the best in breed and negotiate price. Those are our second tier thing.
Raakhee: Third is probably this hybrid, partnership model. There are vendors out there who we would want to partner with to accelerate our roadmap. There is a balance of build versus partner sometimes and it’s core to what we want to achieve in our roadmap and what timeframes we want to achieve those in. Sometimes partnerships, like certain fintechs with specialized capabilities or a particular custodian with infrastructure that we don’t want to replicate at this point due to investment and costs. Those partnership structures are important. But even with that, we always try to maintain a lens of optionality. We never want to be so dependent on a partner that they just control our destiny. That’s always been an anchoring north star for us. In practice, we run a hybrid model, in-house innovation for stuff that gives us our core competency, a best of breed infrastructure for vendors that are commodities and partners that help us accelerate our roadmap.
Craig: That’s excellent. You had mentioned earlier, you’re embedding AI into your architecture. Can you expand on that and talk about some of the use cases that you are seeing that are delivering the strongest ROI?
Raakhee: Where we focused AI on is part of it is in our development process itself. We leverage AI heavily as a co-pilot in the development teams for doing automated testing or setting up automated testing pipelines, data analysis, anomaly detection, focusing on dealing less with paper. In terms of account opening and dealing with documents, doing more document extractions and things like that. Those are areas in which we are finding that there’s a good ROI in terms of efficiency. At this point, we’re not looking to do fully automated autonomous AI advisors, AI replaces every single person, that’s not the focus right now for us. We’re being pragmatic, and we’re looking at it as an efficiency augment, so that we can take something that takes a long time, including from the point of view of the developers, not just the business. We try to embed AI into those, so more co-pilots, like client intelligence, marketing, CRM. That’s another area in which we’ve leveraged AI a lot. There’s amazing tools out there for creatives, and we are dipping our toe in AI when it comes to content, marketing, and embedding it into our customer acquisition side of things as well.
Craig: Terrific. Do you have any specific AI tools you can talk about, which ones you like, which ones you’re seeing the most traction in your firm?
Raakhee: We’re experimenting with various LLM models, like most. In terms of tools, we’re probably more low-level leveraging LLMs and embedding them into our tool sets.
Craig: So your developers use Copilot and those types of things.
Raakhee: Obviously, in terms of the marketing side of things, there’s Banana. There’s so many of these tools out there that we’re opening up the doors for our departments to experiment with. A lot of core stuff is still tied to leveraging Langchain and other types of products like that, as well as various LLMs and fine-tuning what we’re doing with those tools.
Leadership Through Culture and People-First Transformation
Craig: We are almost out of time. I have one more question I’m going to squeeze in. For other CTOs who are taking over a new role, coming to new firm like you did a year and a half ago, what’s the best advice you can give them to be able to hit the ground running and be productive in their first year and a half?
Raakhee: Technology is a interesting area to be in. I’ve worked with and for a lot of brilliant people, and the areas in which I’ve seen people come in and really hit the ground running and provide an impact are those that can focus on not technology for technology’s sake, but just have the North Star of I want to understand and learn where this business has problems. Every firm is different. The core problems for them at a high level might be the same. But when you dig down into it, where are the real problems? And where are the cultural problems? Sometimes issues are there because, and just going and being a bull in a china shop to change things sometimes it doesn’t work out.
Raakhee: You need to have a keen understanding of people and culture and the problems. It is a finessing type of job. Even though you know what the right solution is, if you’re not bringing everyone with you, it’s going to be a short-lived tenure, or it’s going to be impossibly stressful and just no fun. You can’t just be the only one fighting and nobody gets what you’re doing or understand. Sometimes doing that is a slower start. Over time, I’ve found that strategy works well. Even though our roles are technology enhancement, it is a lot about people and culture and bringing people along with us on the ride.
Craig: Raakhee, you’ve said it all here. Where can people who are listening find out more about Siebert Financial?
Raakhee: Siebert.com. Please go there. Another part of my duties was our rebrand. It’s a nice looking rebrand. Please check it out and check out our services.
Craig: Excellent. Thanks so much for being here, Raakhee. I appreciate it.
Raakhee: You got it. Thank you for having me.
Conclusion
In this episode, Raakhee Miller details the strategic overhaul of Siebert Financial’s technology stack, moving the pioneering discount brokerage into a new era of digital service. By focusing on end-to-end modernization rather than just front-end aesthetics, the firm is addressing the root causes of operational friction. The discussion provides a roadmap for wealth management executives on balancing homegrown innovation with vendor partnerships and leveraging artificial intelligence to enhance, rather than replace, the human element of financial advice.
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