Jess Conroy, CEO of ROH, on Building the Financial Core Hotels Never Had

Most of us assume that major hotel brands have sophisticated financial systems running behind the scenes. In this episode, Jess Conroy, CEO and co-founder of ROH, explains just how wrong that assumption is — and why she’s spent the last several years building the financial core that hospitality never had.

What We Covered

• The manual payments problem hiding in plain sight
• Why the biggest hotel brands have the biggest challenges
• The hidden complexity of every hotel transaction
• Why the hospitality industry was overlooked by fintech
• How ROH got its start in meetings and events
• What “AI-first” actually means at ROH
• How ROH fits into the existing hotel software stack
• The go-to-market reality of a franchise-heavy industry
• A transaction-based model that aligns incentives
• Scale and growth: managing over $1 billion across the portfolio
• The stale data problem driving bad hotel decisions
• The vision: a financial foundation for every hotel dollar

Key Takeaways

• Hotel payments are a solved problem almost everywhere except hospitality itself — the industry’s bias toward “human solves” left it behind.
• The complexity of hotel transactions (variable pricing, upgrades, OTAs, group contracts) makes automation far more valuable here than in simpler retail or restaurant contexts.
• Building something that didn’t exist before is the hardest sales motion — you’re not replacing a known tool, you’re educating a market about a problem they’ve learned to live with.
• Year-over-year expansion within existing hotels is the clearest signal of product-market fit — customers keep expanding their use once they’re on the platform.

About Jess Conroy

Jess Conroy is the CEO and co-founder of ROH, a financial infrastructure platform for hotels. A second-time founder, she has spent nearly 15 years building in and around the hospitality industry. ROH is currently managing over $1 billion in hotel transactions across its growing portfolio.

Read a transcription of our conversation below.

FINTECH ONE-ON-ONE PODCAST NO. 578: JESS CONROY

Jess (00:10): So if you are booking a room right now through a hotel central reservation system, that system most of the time cannot actually manage that transaction. So someone behind the scenes is manually taking whatever card you put in there and taking that data, pasting it into another piece of software, then referencing what you actually booked, manually calculating what they now need to process that card for, and manually charging that.

Peter (00:40): This is the Fintech One on One podcast, the show for fintech enthusiasts looking to better understand the leaders shaping fintech and banking today. My name is Peter Renton and since 2013, I’ve been conducting in-depth interviews with fintech founders and banking executives. Most of us who travel frequently assume that hotels, especially the major brands, have sophisticated financial systems humming along behind the scenes.

In this episode, I sit down with Jess Conroy, CEO and co-founder of ROH, to discover just how wrong that assumption is. Jess reveals that the hospitality industry has been almost entirely overlooked when it comes to financial infrastructure, with hotels of all sizes still relying on manual processes to capture, reconcile and track payments. From the individual guest checking in at the front desk, to the seven-figure group and events contracts that drive a significant share of hotel revenue.

ROH is building the financial core that hotels have never had — an AI-first platform that provides real-time visibility into every dollar flowing in and out of a property, automating the reconciliation work that currently consumes entire teams. Jess shares how ROH got its start solving the messiest part of hotel finance — meetings and events — and why that foothold revealed just how wide open the opportunity is across the entire hospitality stack. She also explains the go-to-market realities of selling into a franchise-heavy industry, how the company’s transaction-based model aligns its success directly with hotel profitability, and why ROH is already managing over a billion dollars across its hotel portfolio. Now let’s get on with the show.

Peter (02:38): Welcome to the podcast, Jess.

Jess (02:39): Thank you so much for having me, Peter. Excited to be here.

Peter (02:42): My pleasure. So let’s kick it off by giving the listeners a little bit of background about yourself. Tell us what you’ve done in your career to date.

Jess (02:51): So after business school, I started building another company in the hospitality innovation space. I’ve been building in and around the industry for almost 15 years now. And as a second-time founder now with ROH, I think you have a very unique perspective that you bring to building a company. You get to learn from all of the previous big learning moments, if you will, and really incorporate those into your second chance. And it creates a really special environment, both for you as an entrepreneur, but also your stakeholders and your team, because you’re a lot more intentional, I would argue, about what you’re building, why you’re building it, and where you’re investing, which is what we’re doing with ROH.

Peter (03:37): How do you describe ROH? Tell us a little bit about what you guys do.

Jess (03:40): ROH is a financial infrastructure play. It’s really hard to believe that the hospitality industry and hotels specifically were never given a financial core. But when you think about this business and you think about this industry — you have variable pricing, you have global clientele, you have distributed inventory, you have pricing structures that are incredibly dynamic. I can go on and on, and yet this industry has often been overlooked when it comes to the core financial products. It needs to not only manage revenue visibility, but also have profitability and be able to build better margins, stronger experiences, and just a stronger business overall.

Peter (04:31): Let’s dive into hospitality fintech, shall we say, because it’s an interesting area. I stay in hotels all the time. I don’t really think much about it. I do events in hotels. I’m curious — you’re not just talking about someone coming into a hotel, putting their credit card and driver’s license down and then going off to their room. I mean, that seems to me like a pretty efficient system. What are the pieces that you’re talking about?

Jess (04:59): Well, actually, Peter, my question for you would be — the last time you booked a hotel room, I would encourage you to look at when and where your card was actually processed. So if you are booking a room right now through a central reservation system, that system most of the time cannot actually manage that transaction. So someone behind the scenes is manually taking whatever card you put in there and taking that data, pasting it into another piece of software, then referencing what you actually booked, manually calculating what they now need to process that card for, and manually charging that.

Peter (05:45): Are you serious? That sounds crazy to me.

Jess (05:49): It sounds crazy to all of us. And as I said, building here for 15 years, I’m still surprised by what we uncover with every single hotel that we work with. But that example is just the tip of the iceberg — you multiply that by the hundreds of thousands of transactions a hotel is processing every single day. And that same manual need, that same manual intervention to actually make money move inside a hotel, is what exists today.

Peter (06:23): Yeah, because that makes sense. Sometimes I prepay a room — I was actually in California over the weekend and that was a reservation where they wanted me to pay one night and then the rest of it was done later. And then sometimes you don’t pay anything until you’re checking out, so it can be a little convoluted. I assumed, of course — I’m staying at the big brands usually — I assumed that they have really efficient payment systems that just handle all that. But what you’re saying is it sounds like even some of the big guys aren’t doing this efficiently. Is that what you’re saying?

Jess (06:54): Honestly, Peter, it’s the biggest guys that have the biggest challenges. Because if you think about the large hospitality brands and you think about running a hotel, there has been this hope that there could be sort of a single system. But when it really comes down to it, these businesses are so complex that you need multiple different large systems to help these hotels operate. It’s not like a restaurant where you just have one source of revenue. When you think about where all the different opportunities for a hotel to drive revenue come from, you have multiple different systems. As a result, you have had embedded fintech in some ways try to insert itself inside each one of these different systems. And so you end up with an amalgamation of different software systems, all trying to process payments and provide visibility. And as a result, you end up with no visibility. You end up with massive teams at every hotel, manually trying to reconcile and understand exactly where a specific transaction is.

And that example you gave a minute ago is one of my favorites. You would have someone manually on property trying to reconcile — okay, Peter paid one night, but now we need to bill him for these other two nights. And did that first night come through an OTA? Or did he pay directly with us? What is the rate on that? Did he end up upgrading his room at time of stay? And you realize that every single transaction at a hotel is flooded with this ambiguity where the original value of that booking or of that contract, as we like to talk about it internally, is never the realized value of what you initially bought, which is where so much of the complexity lies inside hospitality. You go and purchase a sweater and you walk out of the store — what you purchased from the time you decided to buy that sweater and the time you walked out with it did not change. Or in a restaurant, same thing — you order a burger, you get your burger, nothing changed. Hotel — you’re upgrading the burger, you’re adding things on to it, you’re deciding you want three burgers. All of that changes. And it’s that complexity that creates so much opportunity for financial infrastructure to remove the need to manually manage it all and actually drive efficiencies throughout the foundation of that hotel.

Peter (09:23): I mean, we’ve got fintech for just about everything these days and many areas of fintech are quite mature. We’ve had a decade or more of innovation happening. Why do you think the hotel business has not had the same level of innovation?

Jess (09:41): I think it’s what you said a minute ago — first there’s an assumption. And even someone who was building in and around this industry for the better part of a decade before we launched ROH, we stumbled into it. I remember the first time I realized there was no financial core and that everything was happening so manually. And I was surprised. But I think more than that, not just the opportunity being overlooked — one of the things that’s so special about the hotel industry is the experiences and the in-person experience and the value on guest experience and interactions and having the right people to make those experiences special. But that bias for the importance on people, I think, has spilled over a little bit into all operations of a hotel where we have over-favored in some cases the human solve versus the opportunity to invest in the right software. And understanding that it’s not one or the other — I think that’s a conversation that’s happening right now with hotels, especially when you think about where we are with AI and innovation. Realizing that you don’t want to sacrifice the magic of hospitality and that human interaction and expect technology to be able to do everything, but you also need to understand that there are real opportunities where technology would be a better solve than a person. And I think it’s finding that balance. I think we swung the pendulum a little too far in the human solve versus the technology solve, and now we have to bring it back a little bit.

Peter (11:18): So how should we think about you guys? Are you primarily a payments processor? You talk about being a financial core. What is the financial core for hotels?

Jess (11:28): So payments is one piece of what we do. And I think that’s the key here — when you think about financial infrastructure, it’s really creating that visibility where you can follow the journey and the data and all the in-betweens from the point of conversion of that sale all the way through to reconciliation. And with ROH, it’s not just inflows. That’s where we started — we started with just managing dollars coming into a hotel and creating that visibility — but it’s also outflows. And when you ask us what our vision is, it’s that at any moment in time, a hotel could have real-time revenue visibility into what is actually happening. Whereas today, that’s close to impossible.

Peter (12:14): You’re talking about the individual just arriving at the hotel, putting down their credit card and managing that process. Are you also talking about the events side? Because I got into fintech through events basically, and I used to organize large-scale events. We would have a seven-figure food and beverage bill at a hotel. We’d have massive thousands of room nights in a room block. Do you handle that as well?

Jess (12:40): That’s where we started. So when you were managing those events, I imagine — how long ago was this?

Peter (12:47): We sold our events business in 2023.

Jess (12:49): Okay. So you were getting PDF contracts. You were getting paper invoices, asked to put in your credit card number into some sort of a PDF. And the team was then taking all of that at the hotel and manually inputting your credit card into whatever system they were using, manually sending you invoices. Did you get payment confirmations?

Peter (13:15): I don’t remember.

Jess (13:17): And that is where we started because that is arguably the messiest part right now for a lot of hotels — the group and events and catering side of the business. That was sort of our foothold with ROH. That’s where we started. That was our first product. And we realized how complicated that was. And like you, we just assumed that there was something at the front desk check-in, that there was something for OTA management — we just assumed that these other systems existed and maybe just meetings and events were the forgotten frontier, if you will. And by building that first product, we realized that actually, no — there’s wide-open space across the entire foundational layer when it comes to both inflows and outflows of money at hotels.

But I love that you have that firsthand experience because that’s exactly what we saw. If you worked with a hotel today, Peter, that was on ROH, all of that would be automated. E-signatures, full visibility into your payments flow as a customer, the ability to get payment confirmations automatically, choose how you want to pay, and then all the visibility back to the hotel. So no reconciliation, no opportunities for them to forget to — when you decided last minute that you guys wanted to add on a breakfast for VIPs or host a pre-happy hour and you’d have to sign off on an additional addendum to that contract and the hotel would have to remember to invoice you.

One of my favorite stories is we have an investor who is a seed investor, early believer, and then came in with his own fund in ROH as well. And he also is a big believer in in-person events and built his whole business by building these events. And he always jokes with me that he doesn’t want me in the hotels that he hosts his events in, because he knows for a fact that they are leaving money on the table and it is to his benefit at this moment.

Peter (15:08): Before you guys came along, hotels had software systems. Does ROH win as a complete replacement or are you integrating with these SaaS platforms that are in the hotel business?

Jess (15:23): So the beauty of where we’re building and what we’re building with ROH is that we are not dependent on integrations for data. As an AI-first company, we’re not trying to bolt on AI to existing software and legacy operations that we’ve built. We’ve actually been able to build everything so that you can be an underlying layer. Because when you look at the existing software stack of a hotel, you have a property management system — a PMS as it’s called inside the industry. You often have some sort of a CRM, or a client management system. And then you have an ERP system. That’s just the high level, if you will. None of those systems were built to manage any of the payment infrastructure. And so right now, when you think about what ROH is doing, all of what ROH is doing is augmenting the manual tasks that are being placed upon the back-office hotel staff and oftentimes the front desk manager and the catering sales associate and every single person at the property who is being forced to manually bridge all of these gaps if they’re not using ROH.

Peter (16:42): You go into a hotel — say, this is great, we want to have this. Are you typically starting on the event side? Are you typically going in with the whole suite? How do they get started?

Jess (16:52): Yeah, we go in with the whole suite because otherwise it’s just a point solution and you’re not actually able to solve the underlying problem. If you just create visibility in one business line, but then you still have to manually manage and reconcile across all the others, there’s still a lot of value and there’s still a lot of visibility, especially if a hotel has a very large meetings and events and group business. But the real value of ROH is a single point of truth. And that is really the key value proposition — that visibility. There’s no more weekly meetings trying to figure out where something is, what paid, what didn’t pay.

And the thing that is probably one of the biggest opportunities but also challenges with ROH is that you’re building something that didn’t exist before. And so your question a moment ago — well, what are you replacing? That would be an easier sale because you could say, hey, this thing that you already know what it does, we can do that better. Mentally, you’re not trying to create a new line item in a budget. You’re not trying to educate an entire market to get them to understand what the opportunity is.

And when we talk to hotels, so often you’re not hearing “I have a payments problem” or “I have a financial visibility problem.” No one is saying, “Hey Jess, I’d love financial infrastructure.” That’s not what’s happening. Instead, it’s things like, “Hey, we’re looking to hire a new firm to help us chase dollars we might have missed.” Or “We’re looking to hire an auditor or a reconciliation firm to help us with OTA because we know we’re leaving money on the table there.” Or “We’ve hired an outsourced firm to help us capture payments more efficiently because we know that our catering sales team isn’t always able to invoice at the exact same time.” You see a lot of that, right? And those are all symptoms of the greater problem that ROH is solving.

Peter (19:01): I think you said that you feel like ROH is an AI company. Tell us a little bit about what you mean there and how you’ve brought AI into your solution.

Jess (19:11): I think the key is that for ROH, we’ve built the business where you’re AI-first, so that you’re not dependent on legacy systems and legacy software. And really, to be a next-gen company — the combination of software and AI together and not being one or the other, but owning the data source and the infrastructure play when you’re talking about AI specifically, as well as being able to leverage that with your own AI. It’s those two pillars together that is at the core of ROH. So you’re not just one or the other, which I think is key here.

Peter (19:52): When you’re coming in, you’re pulling data from other sources, right? And you may have to, in the implementation phase, I imagine there’s a lot of document automation with PDF flows and that sort of thing. But it sounds like once someone’s fully implemented, those things are replaced. So how does the data flow change?

Jess (20:13): The biggest thing is that right now all the data is manual. And that I think is like — we hear from hotels that they have weekly meetings to try to understand where revenue is and credit meetings to understand what they need to go get and receivables and past due and all of this. And all of those reports are manual, where you’ve got someone on property pulling it together.

With ROH, they’re no longer manual. They’re all just at your fingertips. And we’ve heard from great hotels that really use the software — by using ROH, they’re using AI every single day to augment their own productivity, which I also think is really key here.

What used to take someone’s team — we have this great quote from this complex hotel with multiple different buildings that they’re selling, spaces that they’re selling, multiple different revenue opportunities. It used to take their sales team a couple of days to pull what they needed to pull every week for these meetings. Now it gets pulled in an hour. And so that’s what you start to see happening.

That then compounded with the fact that if you think about it, that means that every time they were looking at data before, it was incredibly stale. And that is something that you see across the industry in a lot of ways — that real-time visibility is really what the opportunity is. That means that you can make decisions. Imagine that you were stuck making decisions on data that is already — by the time you look at it, by the time you’ve gotten it into whatever system that you’re trying to put it into to then be able to have it give you some sort of an analysis — that data is incredibly stale now, especially in today’s world where things are changing minute to minute.

Peter (21:53): Do you interface with some of these real-time payments? Like when you’re talking about payments processing, it seems to me like hotels are very credit card-centric. Are you a credit card-centric company when it comes to processing payments or are you also looking at other rails?

Jess (22:10): We look at all the rails, so that I think is the key here. But you still see predominantly — you see upwards of 60 to 80% of purchasers choosing to pay with card, even when given the option for ACH and e-check and other rails. There is a strong preference for credit card in this market.

Peter (22:29): I think I read that you have preferred vendor status with some of these major brands. What does that mean? And if you get preferred vendor status with Marriott or Hilton, does that flow down to thousands of hotels immediately? How does it all work?

Jess (22:45): The beauty of this industry is that every hotel has its own DNA and its own unique ownership structure. You typically have an asset owner who owns the physical underlying asset, as well as a hotel operator in that relationship that’s actually managing the day-to-day operations of that hotel. And as a result, when you get these preferred partnerships, they’re incredible because they provide brand validation, but you have to go sell every one of those assets individually for the most part. And that is where some of the moat of ROH exists — in that we help create an underlying layer of standardization while still allowing each one of these hotels to operate with their own unique DNA.

But you’ll see a lot of people talk about, “We just got this partnership and it unlocks 800 hotels.” It’s just giving you the opportunity to have 800 conversations and a warm intro in the door. But you actually have to individually onboard and activate every single one of those hotels.

Peter (23:56): Do you have to go out then with your sales force and say, here’s what we can bring you? And it’s an individual conversation — there’s no top-down saying everyone’s got to do this?

Jess (24:07): I wish, Peter. You do a lot of webinars, you do a lot of education. And what’s nice about the industry is there are network effects. So what we see happening is if you do well for an asset owner or an operator inside one hotel, they want you in their other hotels. Right? And that is incredibly valuable for us.

You also build relationships with the GMs and the director of sales and marketing and the heads of finance at hotels. And they also move around to different assets, and they will pull you into their hotels. One of our newest hotels that went live a couple of days ago — it’s because of a GM that left one property, went to a new property. And one of the first things he’s doing is implementing ROH because he has an incredible use case.

This might not mean much to you, but inside the hospitality industry, he lost his two figureheads — his DOSM and his head of finance — within a one-week period. And as I told you, everything happens so manually. Before ROH, if that were to happen at another hotel, everything stops because there’s no one to manage any of your inflow or any of your outflow. With ROH, everything keeps moving because everything is automated. And so this GM was able to basically keep the lights on — that’s an overdramatization of it, if you will — but he was able to keep everything moving and have this visibility, log in, work with — we call it Robot, which is our AI — have visibility, make sure that his teams weren’t missing a beat. And for him, it’s become that right hand that he’s now bringing with him to his next property, which is huge for us.

So you see that as well. And you see the same thing with asset owners who see what ROH has done, how we’ve helped drive profitability inside their hotel. And if they own multiple assets, they want to bring you along to the other assets as well.

Peter (26:03): How do you guys make money? Are you really a SaaS platform? Do you also do transaction fees? What’s the business model?

Jess (26:11): We’re a transaction-based model. We like to say that we only make money when the hotel makes money.

Peter (26:15): And you take a piece of each individual payment then? Is that the same for the events side as well? Can you give us a sense of the scale you guys are at? What’s the volume going through?

Jess (26:29): So ROH right now is managing upwards of a billion dollars across our hotels. The biggest metric for us that we really focus on is: are we growing within every hotel that we work with? And one of the things that we’re most excited about right now is that year over year, invoice generation — day over day, which is the most important thing — is up 150%, which is huge for us inside our hotels. Because you want to see them expanding horizontally across that hotel and having them pull you into all the different opportunities where ROH can help provide that visibility, that revenue orchestration layer, if you will — stronger, more profitable, and all of the benefits that you see. You want to see that compounding inside every single asset.

Peter (27:17): So if I’m staying at a ROH hotel versus a non-ROH hotel, is there anything that I would notice that’s different?

Jess (27:24): You might have a more pleasant conversion process, a more pleasant opportunity to receive payment confirmations, but no — if we’re doing our job right, you shouldn’t see a difference.

Peter (27:33): When you’re out and about, when you’re traveling around, I presume you try and stay at hotels with ROH? Or do you actually try and stay at hotels that aren’t using ROH so you can sell them?

Jess (27:43): I try and stay at hotels that aren’t using ROH. My husband won’t sit with me when I check into the front desk anymore because I like to pretend that I don’t have my wallet to understand what they’re going to do. What system are they going to use to try to compliantly capture my card details? When is that card going to be run? All of that, because I know that even though I’ve booked online with the central reservation system, the card I put in the central reservation system — those systems don’t talk to each other, right?

So we typically get to a hotel and I’m like, I don’t have my wallet. How can we do this? And I want to see what’s going to happen. It does increase the time to check in, I will say. But it’s a huge learning too, because it creates validation a lot of times. And it also allows us to learn, to see what is happening, what new technology is being used, how teams and hotels are thinking about that experience.

And I think that’s the thing — more and more as transactions and dollars and everything move away from any in-person experience, we will get closer to a place where that check-in experience will no longer require this exchange of financial details the way it does today.

Peter (29:04): I was staying at a Westin last year in New York and they didn’t have Apple Pay because I had my card in my wallet, in my backpack and I didn’t want to go digging for it. I said I’m just going to Apple Pay. And they said, we don’t take Apple Pay. Most Hyatt hotels seem to take Apple Pay. Is that typical for what you see?

Jess (29:25): I think the friction that you’re talking about is what is typical. There is a friction to transact that I think is everywhere inside hospitality right now. We’ve got this great guest experience, but then — oh, that’s how you’re actually going to pay? Are we going to allow Apple Pay? It doesn’t factor into the guest experience.

Peter (29:49): Last question then — what’s your vision here? Are you looking to be the only software that a hotel has, or where are you taking this?

Jess (29:58): Our goal with ROH and where we are is to be that financial foundational layer for hotels, so that as we continue to build in the next generation and you have all the opportunities of AI that will drive massive top-line growth in this industry — and if you look at hospitality, that’s where a lot of the focus is right now, right? How we leverage AI in revenue-generating activities, because that’s always been the focus inside hospitality — top-line growth, because of this assumption that it was a fixed-cost game.

ROH is transforming that notion of hospitality being a fixed-cost game by making every dollar more profitable with our infrastructure layer. But it allows hotels to take more advantage of that top-line growth. And so as we continue to build, our goal is that we would provide visibility for every dollar that flows in and every dollar that flows out for every hotel.

Peter (30:53): Okay, well, best of luck with that, Jess. It was really interesting to learn about a new vertical that I’ve never really covered before here on the show. So thank you very much for coming on, and best of luck to you.

Jess (31:04): Thanks for having me, Peter. I really appreciate it.

Peter (31:13): As someone who has stayed in a lot of hotels over the years, I was amazed that their financial systems are still so backward. The fact that hotels today are doing manual reconciliations and making decisions on stale data is a travesty that needs fixing. What ROH is doing is bringing hotels into the modern world, along with most other industries. By building AI-first systems from the ground up, rather than bolting it onto legacy systems, ROH owns the data layer in a way that compounds in value over time. That stat she cited — invoice generation up 150% year over year within existing hotels — is the clearest evidence that hotels, once on the platform, keep expanding their use of it. Anyway, that’s it for today’s show. If you enjoy these episodes, please go ahead and subscribe, tell a friend, or leave a review. And thanks so much for listening.