Technology Investments That Work: Aligning Strategy, Data, and ROI

Don’t just invest in technology—invest in results. In this episode of the Oyster Stew Podcast, experts Dan Garrett and Jay Donlin break down the critical—but often overlooked—factors that determine whether your technology investments will actually move the needle for your firm. From setting business-driven goals to avoiding the allure of flashy tools with limited value, they walk through practical insights that can save you time, money, and internal frustration.

Ensure Your Technology Investment Advances Business Goals

Here’s what you’ll learn in today’s episode:

• Start with Strategy, Not Software
• Beware the Shiny Object
• Don’t Underestimate Adoption and Training
• Data Strategy
• Measure Before and After: ROI Isn’t Optional
• Knowing When to Walk Away
  

Whether you’re considering AI adoption or evaluating more fundamental systems, this conversation offers essential wisdom for anyone responsible for technology decisions. Listen now to ensure your next technology investment truly advances your business goals rather than becoming another expensive disappointment.

Listen now:

Additional Resources

How to Perform a Technology Audit

Hidden Costs, Smart Choices: Mastering Your Technology Stack

The 5 C’s of Successful Digital Transformation Strategy

Partner with Experts Who Turn Technology Investment Decisions into Business Results

Technology investments are only valuable when they support your firm’s strategic objectives, drive meaningful outcomes, and deliver measurable returns.

Oyster Consulting brings a business-first mindset to every technology conversation. Our team of experienced professionals works alongside your firm to develop a clear, actionable strategy that aligns with your long-term goals. Whether you need help performing a technology audit, evaluating vendors, creating a data strategy, or measuring ROI, we help you cut through the noise and make smart, informed decisions. Our experts understand the human side of technology—change management, training, and adoption—and guide your team through implementation to ensure success. Don’t just invest in technology—invest in results.

Transcript

Transcript provided by TEMI

Libby Hall: Welcome to today’s episode of the Oyster Stew Podcast. I’m Libby Hall, Director of Communications for Oyster Consulting. In today’s episode, Dan Garrett and Jay Donlin share hard-learned lessons and expert guidance on how to make smarter technology decisions from building a business first strategy to avoiding common traps, like chasing the shiny new tools on the market. They cover the full lifecycle of a successful tech investment. Whether you’re exploring AI or just looking to streamline your operations, this episode will help you stay focused on what really matters, delivering measurable results for your business. Let’s dive in – Dan?

Dan Garrett: Good morning. Thank you, Libby, for kicking us off here. I’m Dan Garrett. I’m here with Jay Donlin. I’ve been with Oyster for just over a year now. I’m very happy and excited to be here. We’ve been working with clients on technology strategy, whether that’s data or system improvements, operational improvements, and so forth. I’ve had a great opportunity to go to many conferences over the last few months where there’s just so much talk about AI and technology upgrades and so forth, so I’m sure we’ll touch on some of those things. With that, Jay, if you want to start off with a quick introduction?

Jay Donlin: I’m Jay Donlin and I’ve been with Oyster for probably over six years now, and been helping firms navigate, not only their platforms, whether it be clearing or custody, but also some of their technology stack and other strategic investments or process improvements they need to make. So, Dan, I think it’s going to be a great time to talk.

Dan Garrett: So, let’s just talk about, at a high level, some of the topics that I think get missed when people are looking at technology, things that they should be thinking about, things that they should be reviewing, things that they may underestimate when they approach their technology strategy.

Jay Donlin: Dan, there’s a lot of shiny objects out there when it comes to technology and a lot of people; there’s a lot of good sales reps too at technology firms and they’ll tell you that you need something and sell you on it and you may or may not need it. It’s something that you need to go through and decide -does it really provide value to your firm? Does it provide operational efficiencies or increase production for firms, reps or advisors? What will it really do to help your firm, your clients and/or your advisors? And it’s something that we feel is like a pretty good strategic review of your needs. Each firm’s unique, so you want to make sure that you identify what actual needs you have versus all the chatter on the street regarding technology and like I said, all the chasing of all the shiny objects.

Dan Garrett: It’s interesting that you are presenting it that way because it’s really about starting with, what are the firm’s goals? Forget about the technology. What’s the strategy for the firm? Are we trying to grow? Are we trying to reduce cost? Are we trying to improve efficiencies? Are we trying to provide a better client experience? And having metrics around that too. What does that mean? What are the numbers behind that? And if we want to grow, at what rate do we want to grow? If we want to save money, how much money do we want to save? What are some of the benefits that the technology is going to provide to our financial advisors, to our clients, and having a metric around those things. So having a vision, a strategy for the business metrics around that – and then you focus on the technology. I think so often the technology is there, and like you said, it’s the shiny object and it’s like, oh, we should do this. It’s not about that – it’s about starting with the business, starting with what the business needs are, and then going out and evaluating to see if there is technology that can help in these particular areas and are helping, going to help move the needle on some of those metrics.

Jay Donlin: Dan, it’s exactly right. Even when you go to select the vendor, you have to make sure that if you need to integrate with whatever your providers are, whether it be a commission system or wanting the custody or clearing providers, that they can actually do that. I’ve seen firms go out and invest a lot of money in a workflow solution, and they basically turn into a swivel chair. They can’t get the information out of the system. They invested it in their custody or clearing firm. And so now they’ve just created additional work versus leveraging what the clearing firm had in order to manage the business. Granted, they were trying to address gaps that the clearing firm had. So, they had all the good intentions, but now they’re in a situation where it’s a swivel chair.

They have to take the information out, turn it around, put it into the clearing firm. So that’s really not efficient. It has streamlined some of their work, but it’s something that you need to be cognizant of when you’re looking at firms and looking at technology providers. The other thing is you need to assess your field and your staff. I mean, are they going to adopt it? That’s a big thing. A lot of people don’t like change in general. And so, if you’re trying to force them to change, they have to see a benefit for that. And if it’s just more work or it’s another project I’ve got to do, you might not get the adoption that you want for the product. That’s always, kind of like, “I’ve spent all this money on something and nobody’s using it.” And that’s always a concern.

Dan Garrett: I see that a lot. I see folks kind of underestimating the training and the adoption challenges. And part of that is bringing folks along on the journey of explaining that here’s our mission, here’s our strategy, here’s what we’re going to do, and here’s technology that’s going to help us do that. And, be inclusive of people’s ideas and thoughts as you’re going through the selection process and reviewing the opportunities and so forth to help get buy-in before you’re actually there. It’s that old adage of who moved my cheese, right? I think we see this over and over again at firms where they just, they get in there, they think it’s going to make huge change, and they just underestimate the training, the adoption. And then, you could be spending a lot of money on something that just doesn’t get utilized fully.

Dan Garrett:

Or maybe you’re using 10% of the capabilities of a system but paying for a hundred percent of it. You touched on something else I wanted to dig into a little bit too, which was the integrations not just with your other third-party vendors, but with data. And we’re seeing this too, a lot that firms are really hindered by the fact that they don’t have a data strategy. They haven’t thought it through. They’ve got data all over the place. It’s not centralized. It’s not normalized. And so, without having that kind of bedrock or foundation to build on, any technology solution that you’re bringing in can either create problems, but it can even make things even worse. And I’ve seen clients where, because they don’t have a handle on the data that’s going into the third-party vendors, which is supposed to make things more efficient and effective, is actually making things worse because the data isn’t good data, it’s not trusted data.

So even though there may be an alert or something that the system’s telling you need to do, you have to swivel in a chair, go to another system check to make sure that the data that’s in that system’s correct by verifying it from the main system. And it just creates all of these inefficiencies, and it actually can make you go backwards in operational efficiencies if this isn’t done properly and correctly. So, as we said, it’s the strategy and having the business strategy and then having that foundation on your data and having your data in a good shape and good place. And then being able to build on it from there.

Jay Donlin: Yeah, that’s exactly right. Dan, we were working with a client not too long ago that had gone and deployed a CRM system and imported data from various systems that they had. They spent a year, and it was some time before we got engaged with them. They spent a year going through and cleaning it up.  And it was this huge project for the staff within the organization and even some of the advisors because the data was bad. And so, when they imported it, mobile phone goes into home phone, and now they had to turn around and basically go through every record in the database and clean it up. It was a nightmare for them. They spent a tremendous amount of money on the system acquiring it and then it was a mess to clean up, so there was even more money to clean it up. So, you definitely need to be careful with your data and make sure that you have good data going into anything.

Dan Garrett: Let’s shift the conversation a little bit and talk about ROI and return on the investment. What happens is a system gets brought in, you sign off on the budget and so forth, you implement it. There’s a lot of trouble with all the things that we just discussed. And I think it’s then kind of an embarrassment to go back and say, what was the return on this investment? Did it do the things that we like to do or that we were trying to accomplish? And I think a lot of firms don’t have that strategy. They don’t think about the metrics of what they’re trying to improve. So even after they’ve implemented the technology, whether it was done great or it was a poor implementation, how do you calculate the ROI on it?

If you haven’t really put together a thought around the metrics of what you’re trying to improve and looking at the numbers and the cost of the system and the cost of the operation. And there’s also opportunity cost, because if not you’re doing this, you could have been doing something else. So, let’s talk about the math a little bit, and some best practices around what you should be doing before you acquire a system in the evaluation phase. And then really kind of postmortem looking at, was this a success? Did we meet our goals? Because I think a lot of times that last step gets skipped and sometimes the first two steps get missed as well.

Jay Donlin: Yeah, I think you need to get pretty specific on metrics. I mean, you have to define what success means. So, if it’s okay, we want to increase production by 10%, then how do you measure that? Do you measure it just as straight production? Do you measure it as something within this system that you purchase that you feel like you can tag to and say, that’s the number I need to monitor. Or if I want or I need to increase efficiency, are you looking for hours worked on the administrative support staff? Are you increasing business but you’re not increasing the hours worked and things are still getting done and they’re getting them timely measuring time for processing things. You need to be thoughtful in figuring out the metrics that you want to look at or feel like you need to look at, because those are really the points that you’re trying to address anyways. But you have got to figure out how to measure it. And if you can’t figure out how to measure it, you’ll never figure out, did it really make a difference.

Dan Garrett: One thing I wanted to ask you, this is going to be a tough question, Jay. I’m throwing you a hardball here because I’ve struggled with this my entire career, and I would love to get your thoughts on it, and that is around when do you call it off? When is a breaking point in an implementation where you just decide the best thing to do is to stop and quit and move on to something else? Like you’ve said, we’ve seen these case studies. CRM is a good example. We hear stories all the time of somebody investing a lot of money into an application, they realize it’s more difficult and going to be a lot more expensive than what was originally thought. They keep plugging more and more money into it and trying to solve the problem. Timelines get extended and extended and extended. When do you say, okay, this is not going to work. We’re never going to get a return on this investment. It’s just something we need to stop and move on with.

Jay Donlin: I think it’s a hard thing to tackle, right? I mean, because you’re invested in the system, you’ve spent money on it, you spent all this time, people in your firm have spent time, they’re invested in the implementation, but there is a point in time where you have to basically shake off the cobwebs and say, wait a minute, this is not going right. And I’ve seen firms spend tens of millions of dollars implementing the CRM and they get 10% utilization. And it’s at that point it’s like, I’m solving 10%, but is that really enough? And how can I either adjust my processes to make it more palatable or increase adoption, or do I cut bait because it’s costing me all this money, and I’m not getting the return.

Again, it goes back to the metrics. You have to define what you feel like measures your success. And it is a hard question when to cut bait. We’ve seen firms make decisions to go to other clearing firms or custody firms, transfer their book of business and after two years they’re like, I can’t do it anymore. I have to go back. And they <laugh> are going back to their firm. But these are huge decisions with huge investments that they’ve made. And it’s hard to make that decision, but sometimes it’s the best thing to do for your firm.

Dan Garrett: Yeah, that’s great. Thank you. Well, Jay, this has been great. I really appreciate the time and opportunity to kind of kick around some ideas with you. I think just to summarize the major points and make sure I’ve got it all here. We kind of talked about, first and foremost, focusing on the business strategy. What are you trying to accomplish from a business goal? Don’t get distracted by the shiny, flashy, new thing that’s out there which is AI right now, but there’s some great opportunities there for sure. Focus on the business first and foremost. Come up with your metrics of what you’re trying to do, your goals, so it’s very clear what those metrics are.

Then, go find a partner and a solution that you know is going to help you tackle those issues and be able to accomplish some of the metrics that you put forward. And being aware that you do not want to underestimate the training and acceptance criteria. Making sure that your staff is along for the journey and is accepting the new systems and the new opportunities and the business goals. And then knowing when it’s time to make a change and to stop something that’s just not working and to move on. So those are all great points. Did I get it all? Is there anything I’m missing there?

Jay Donlin: You got it.

Dan Garrett: Alright, thank you so much.

Jay Donlin: Thanks all.

Libby Hall: If you found today’s discussion helpful, don’t forget to subscribe for more episodes where we dive into industry strategies and best practices. For more information about our experts and our services, visit our website at oysterllc.com. Thanks for listening.