Good morning!
Welcome to the very first “In the Chair” interview. When I announced this series a few weeks ago, I promised access to seriously impressive finance and payments leaders - and I’m thrilled to kick things off with Brandon Goeke, the newly minted Chief Operating Officer at Florida Prepaid College Board.
For those unfamiliar, Florida Prepaid is one of the largest and most established 529 prepaid tuition programs in the country - we’re talking half a million active students in the program, with around 100,000 currently in school. At some Florida institutions, they represent up to 30% of undergraduate enrollment.
And if you’re wondering why a 529 plan leader is relevant to you - whether you’re in a Bursar’s office, financial aid, or working with third-party payments - stick with me. The challenges Brandon and the team are solving are eerily similar to the ones you face every day: legacy systems, change-resistant processes, collaboration headaches with institutions, and the never-ending quest to do more with less.
Lets get into it!
The Journey to COO
Callum: Brandon, you’ve been at Florida Prepaid for 13 years now. That’s a long time at one organization. How did you end up here, and what’s kept you around?
Brandon: My background is actually in project management. I worked in the private sector for an engineering design firm, doing project management and technology implementations. From there, I moved briefly into higher education administration - working in a functional business office for an academic unit.
It was through some connections I had developed at the university, in the division of finance administration, that I learned about Florida Prepaid. I came on board in what was initially a special projects role during a technology implementation.
From there, I was fortunate to move through a number of different roles in the organization - all of which had some level of engagement with data and our school partners. Over time, that positioned me for the executive path.
Callum: What’s kept you there for over a decade?
Brandon: The people and the mission. I’ve been fortunate to work with a passionate team that’s dedicated to higher education. That passion is contagious, and it’s what’s kept me engaged for so long.
Priorities as the New COO
Callum: You were recently promoted to COO. What are your top priorities in your new role?
Brandon: The big focus right now is operationalizing a lot of the technology we’ve been building over the past several years. We want to drive high-value engagement - especially as we head into 2026.
That means two things. First, integrating with state entities to attract participants to our 529 products. Second, integrating directly with institutions or third-party providers for benefit payments.
The goal is to scale what we do, engage with our customers in a high-value way, and get through the routine stuff so our team can focus on more personal engagement - helping families with their saving goals, their benefit utilization, and streamlining obstacles they might face.
Callum: And generative AI is a big part of that, right?
Brandon: Absolutely. We’re leveraging generative AI in our customer service channels - chat and voice. Actually, we just went live about a week ago (Jan 2026).
The idea is to handle the basic, frequently asked questions through AI so our team can engage more personally on where families are headed, why they’re saving, what they’re doing, and how to best utilize their benefits. Lets get through the FAQs so we can focus on the high-value engagement.
The Foundation: A Five-Year Data Journey
Callum: One thing I always tell people is that you can’t do any of the exciting AI stuff without clean, consolidated data first. I imagine that’s been a journey for you.
Brandon: I don’t think you could overstate that journey.
We came from an environment where we had a transaction management platform that was separate from our contact center platform, that was separate from document management, that was separate from our online engagement and website. Bringing all of that into one ecosystem - that’s been an evolutionary process over the last five or six years.
Callum: What does that consolidation actually enable?
Brandon: A few things. Real-time visibility into customer behavior. Continuity of experience. And now our team can see the same data our customers see.
Now someone can log into our website, transition immediately from our marketing site into an authenticated web experience that’s tied directly to our underlying records administration platform. They’re seeing information in real time, they can access their documents, and our team can see that same data to support them.
Callum: And that foundation is what makes the AI work.
Brandon: Exactly. You have to overlay a strong knowledge content database so you can leverage things like generative AI. You have to be very deliberate in documenting information and rooting your AI in that knowledge base so you can feel confident you’re delivering accurate and appropriate responses.
Without that consolidated data and that knowledge foundation, AI just doesn’t work the way you need it to.
The Hard Part: Unintentional Resistance
Callum: Let’s talk about the hard stuff. You’ve spent years working with universities to implement change. What’s that actually like?
Brandon: There’s unintentional resistance, right? At its core, change is hard.
When you’re changing how customers interact with data, how your own internal team interacts with data, how business partners interact - you’re being disruptive to their business processes. That’s not easy.
I want to emphasize “unintentional.” It’s not that people don’t want to improve. It’s that the changes are disruptive to what they’ve built over many years. You have to be sensitive to that.
Callum: How do you navigate that?
Brandon: Early engagement. We often start with our preeminent institutions - the ones that represent a significant portion of our undergraduate population - and we engage them early. We try to understand the hurdles both inside and outside our organization and work through them together.
The industry generally agrees on the need for efficiency and moving processes online. The difficulty is in the complexity of existing processes and the disparate systems everyone is working with.
The Three Core Challenges
Callum: If you had to boil it down, what are the top challenges in getting students, Florida Prepaid, and universities to work together seamlessly?
Brandon: There are really three.
First is understanding the institution’s established processes. Most of our partners have processes that have been in place for many years. And typically you’re engaging two different teams - a systems component for their enterprise platform, and a user component for the folks actually engaging with students. Those are different conversations.
Second is securing support at the right levels. These are robust and mature governance structures at these institutions. Decisions are made at different levels for different initiatives. Getting the right people in the room to understand the challenges we’re trying to solve - and what that change means for them - is a recurring theme.
Third is budget and resource constraints. Everyone seems to be facing the same constraints - budget and human resources. Having the resources to actually implement the changes we all agree need to happen comes up time and time again.
Strategies That Actually Work
Callum: So how do you actually make progress when everyone is resource-constrained and change is inherently hard?
Brandon: There are three components to our approach.
First, with our high-touch in-state public institutions, we focus on understanding their processes and finding efficiencies within their existing processes first. We’re not asking them to blow everything up. We’re looking for things that position them for larger changes later.
We’re also fortunate to have collaborative networking groups within the state. Our state universities have collaborative sessions and work groups, and they’ve been very welcoming for these discussions. That helps a lot.
Callum: What’s the second component?
Brandon: We have a mantra in our office: think big, but start small.
What are some incremental things we can do that position us for larger changes later? As we head down a path for integrations, we can identify commonalities in their processes, work together to find commonalities in data structure. That helps everyone and builds momentum.
Callum: And the third?
Brandon: Customer empowerment. Sometimes the best way to eliminate a process is to give the customer the tools to do it themselves.
Are there ways we can put the 529 plan holder or the student in a place where they can initiate payments directly to schools? If we can do that, we eliminate some of the processes altogether that are causing strain on the system.
It’s not about us being in the middle of everything. It’s about empowering families to take action directly when that makes sense.
Scale Matters More Than Geography
Callum: Does your approach differ for in-state versus out-of-state institutions?
Brandon: There are differences in the operating model, but it’s less about in-state versus out-of-state. It’s really a function of scale.
When we represent a small number of students at an institution, that has a significant impact on how they interact with us - how much integration there may be, how much investment from a technology or process perspective they’re willing to make.
Callum: And when you’re a bigger piece of their pie?
Brandon: When you flip that and think about institutions where we may be up to 30% of their undergraduate enrollment, there’s different pressure for how they interact with our data and our students.
Most of those institutions engage with us through some kind of technology process — receiving and submitting data electronically. That process has evolved over time and is currently evolving from secure file transfer to an API structure, which is something new in our technology platform.
Callum: What about the smaller engagements - out-of-state schools, private institutions?
Brandon: Historically, that’s been paper correspondence. It has evolved to a portal experience where someone can look for student information and bill directly. And we’re pursuing self-service options for students to pay directly out of their prepaid and savings programs.
The key is being flexible. We can’t expect a one-size-fits-all model because the scale is different and the ask is very different based on that scale. We think about it as build, buy, or partner - depending on what makes sense for each situation.
The Grand Vision
Callum: Zooming out - what’s the long-term vision for Florida Prepaid?
Brandon: It always comes back to Florida families.
We want to reach more Florida families. Educate them about saving for college and the benefits of doing so. And then on the flip side, make sure we have a flexible and user-empowered experience for them to utilize their benefits when it’s time.
Callum: What does that look like in practice?
Brandon: Multiple paths. Technology integrations with our large partners. Engagement with aggregating partners. Self-service options for direct payments.
The goal is a comprehensive solution that puts Florida families in a better position - more financially prepared to attend college.
Callum: Is this just about Florida, or do you see a broader impact?
Brandon: Our hope is to share what we learn with the broader 529 industry. Share our lessons learned, our experience. If we can figure out what works, there’s no reason to keep that to ourselves.
Lightning Round
Callum: What’s the hardest part of your job?
Brandon: Honestly, it’s the breadth. Jumping topic to topic and then empowering the team to dive deep on the solutions. My core instinct is to dive in deep and problem-solve myself.
But that’s also the most exciting part. I get to wear multiple hats, be involved in multiple strategy discussions. It keeps things interesting.
Callum: Best career advice you’ve ever received?
Brandon: It’s twofold.
First, we have an office mantra: always be able to explain why. Why are we doing this? Why does it matter? It drives disciplined decision-making and more structured decisions. If you can’t explain why, you probably shouldn’t be doing it.
Callum: And the second piece?
Brandon: Advice I got very early in my career: never be afraid to ask questions as the new person. Never be afraid to play that card.
It’s something I’ve really embraced whenever I come into a new role, a new project, a new circumstance. If you have the new person question, don’t be afraid to ask it - and ask it early. It breaks down what might otherwise be a cultural barrier. People respect it. That’s served me well.
Wrapping Up
That’s a wrap on the first In the Chair. Huge thanks to Brandon for the time and candor — this is exactly the kind of conversation I hoped this series would surface.
I thought Brandon’s insights were fantastic. My key takeaways:
Lay the Foundation
Now is the time to do the hard work of consolidating data sources and bringing processes online. Without that foundation, it will be nearly impossible to take full advantage of modern tools like AI. Said differently, modernization doesn’t start with AI - it starts with clean data and connected systems.
Unintentional Resistance
This one hits home, and I’m sure it does for many of us. Driving change is hard - especially when you’re working with processes that have existed for years across multiple teams and stakeholders. Brandon’s emphasis on understanding existing workflows before pushing change felt critical.
Moving Online
Florida Prepaid is a large, state-run institution serving millions of families. Their commitment to building the data foundations needed to modernize shows two things: first, the movement online is here to stay; and second, every institution can do this. The ones that make progress are those that find ways to work within constraints - not fight against them.
If you have questions you’d like me to ask future guests, or leaders you’d love to hear from, reply and let me know.
See you next time.
Cal