Jessie Fischer is the Founder and CEO of GuestOS, an AI-native communications platform that powers real-time, multilingual guest engagement across hotels, destinations, and global events. Under her leadership, GuestOS has gained rapid traction through industry referrals, with its AI teammates handling up to 30% of hotel calls and freeing staff to focus on in-person guest experiences. Drawing on her early experience working in her family’s hotel near Yosemite National Park and as an Airbnb superhost, Jessie brings a unique blend of hospitality insight and tech startup expertise to solving operational challenges in the hotel industry.
Most hotel front desks lose hours every day to the same handful of questions: check-in times, pet policies, directions. Jessie Fischer, founder and CEO of GuestOS, builds AI voice agents that answer those calls so staff can give their attention to the guests in front of them. Kin Sio sits down with Jessie on The Lights On Podcast to talk about AI that protects hospitality instead of replacing it.
Jessie grew up answering guest questions at her family's hotels near Yosemite, starting at age 12. The questions then are the questions now: roughly 70% of what a front desk handles is repetitive. After a decade in tech startups across food robotics, education, and fitness, she came back to hospitality and saw the gap clearly. When ChatGPT arrived, she built GuestOS to handle those FAQs in a way hoteliers would actually trust, instead of adding a tenth or fifteenth platform to a team that already has no time to use the ones they have.
What sets her approach apart is who she builds for. GuestOS is designed around the front desk staff who use it every day, not just the owners and GMs who sign the contract. Within the first 10 days at a property like Luma Hotel in San Francisco, the AI teammate handles about 30% of calls. The product has grown entirely through industry referrals, with no cold outreach, because the operators who use it become its advocates.
This episode is sponsored by Lights On.
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We help hotels identify new revenue opportunities, so they don't leave money on the table. We also manage the full revenue and marketing operation, enabling the on-the-ground team to focus on the guest experience.
If your hotel needs stronger revenue growth, visit lightson.co to learn more.
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[00:00]
Kin Sio: Welcome back to the Lights On Podcast. I'm Kin Sio, CEO of Lights On and your host today. On this podcast, we share stories from across hospitality about building and growing hotel businesses.
This episode is sponsored by Lights On. Lights On helps hotels grow revenue more consistently by managing pricing, distribution, and digital marketing together. We help hotels identify new revenue opportunities so they don't leave money on the table. We also run the full revenue and marketing operations so that the property team on the ground can stay focused on the guest experience. If your hotel needs stronger revenue growth, visit lightson.co to learn more.
Before introducing today's guest, just a big shout out to Frank Amand, Director of Sales and Marketing from Kualoa Ranch, for making this show happen by introducing us.
So our guest today, Jessie Fischer, is the founder and CEO of GuestOS, an AI-native communications platform powering real-time, multilingual guest engagement across hotels, destinations, and global events. Growing up working in her family's hotel near Yosemite National Park gave her a firsthand understanding of how critical communication is to great hospitality. Today she's building GuestOS to replace outdated phone systems with intelligent AI teammates that help businesses serve guests better and operate more efficiently. Jessie, welcome to the show.
Jessie Fischer: Thank you so much for having me.
Kin Sio: So excited to have you. Just seeing what you guys have been building, it's so fantastic, especially in this industry of hospitality. I think people always talk about us not moving fast enough. So I think you are building some exciting tech nowadays to give hoteliers more time to focus on the guests and all that. I'm so excited to dive into that.
Jessie Fischer: Really excited to share more about that and really how we're bringing hospitality to new technology advancements, but really focused on maintaining that human touch.
Kin Sio: Let's go all the way back to where you started. So your family has operated hotels near Yosemite back in the 1970s, right? You started helping out your family at a young age, probably before you were a teenager, right?
Jessie Fischer: Yeah.
Kin Sio: So what was the operational reality of those hotels back then that stuck with you all through your career in hospitality and tech?
Jessie Fischer: I learned so much about just life and nature and how things work in some of the harshest conditions, because Yosemite is extremely remote and around us, the infrastructure is — there is not a lot of infrastructure. Everything is much harder: getting food delivered, getting communication and all of those things, on top of running a hotel, which any hotelier will tell you is difficult in and of itself.
So I learned a lot about that, and international visitors all the time. One of the most popular national parks in the world for great reason — if you haven't been, you have to visit Yosemite. But really just from a young age, being surrounded by travelers and people really excited to immerse in nature and the opportunity to help people have these experiences that last a lifetime. I've always been super thankful for that.
Kin Sio: And speaking about Yosemite, I think people should know they have one of the best pizzas from a national park. Most of the national parks, they all have really terrible food. Yosemite definitely has one of the best. I can't remember the name, but definitely that pizza joint within the park actually tastes amazing.
Jessie Fischer: That is such consistent feedback about the pizza. And I'm not sure — I know pizza is my favorite food, so I've had a lot of pizza and it's incredible. And after those all-day strenuous hikes, that might help a little — pretty hungry, deserving that. But yes, such amazing pizza.
[05:05]
Kin Sio: So as a kid, I'm curious — back then helping out your family, what specific guest question did you answer the most?
Jessie Fischer: Oh wow. I would say all of the FAQs. Every single one of them that hotels have on the page — that is just a loop of what I would always answer. What time is check-in? Can I bring a dog? What's your cancellation policy? And of course, the majority of visitors are there to visit Yosemite, so it's a bunch of other questions as well about how to get the pass, do you have transportation there.
I would say those questions amount to 70% of the questions that we got when I was really young growing up, answering questions at 12 years old, to today. And that's really where I was like, okay, we need to shift our responsibilities so that we can focus more on the guests and less on the same questions.
Kin Sio: And I'll bet that's everything that GuestOS can handle today, huh?
Jessie Fischer: Exactly. I really built GuestOS so I didn't have to answer the questions again. And it turns out other hoteliers have that same challenge. So it's been a lot of fun working with the industry.
Kin Sio: So before GuestOS and after hospitality, you spent probably like a decade in other tech startups running operations and everything you can think of, right? So after the experience outside of the industry, now coming back, building products for hospitality — what did you see with that outside perspective that you couldn't have seen from the inside?
Jessie Fischer: I grew up in hospitality and everyone growing up would say, "Oh, you're just going to work in hospitality your whole life." And I was really annoyed by that for some reason. And I was also fascinated by many other industries.
So I went and I worked at the earliest-stage startups, really zero to one, where they're bringing an idea to life. That's my favorite part. And so going out and being in food robotics or education technology, fitness tech, or architecture in Big Sur and Carmel — I knew quickly I was not going to be an architect.
But then coming back in 2019, right before the pandemic, I started hosting vacation homes back in the Yosemite area. And that's really what brought me back to the guest experience. And then shortly after, ChatGPT came out and I realized that you could finally create a hospitable interaction that was good enough to handle the guest interaction you would trust, and could allow hospitality workers to focus on the in-person.
Kin Sio: Do you feel like there are certain assumptions in the hospitality industry — people would think, "Oh, it's just the nature of the business." But with what you saw outside and from other industries, especially in tech, now coming back, you immediately recognized, "Oh, it's not by default. It is a problem that can be solved."
[10:00]
Jessie Fischer: Definitely. I think there are a lot of legacy technologies in hospitality. And so you just keep layering things up. And for a really long time — it's a really complex industry. And I always laugh when people try to simplify it. It's such a complex industry from back-end operations, how they do things today, and then also just management and franchises and all those other brand guidelines.
So I think it is one of those things where it's just finally possible to build something that is hospitable and that the industry trusts. Because our biggest fear is that it becomes transactional. And that's really why I think a lot of the pushback has been, because we're not that industry. Everyone in it cares deeply about the guests and the teams that run it.
Kin Sio: And I like how you emphasize the term "hospitable." Obviously in tech, almost nothing is impossible with technology, automation, software development, and now AI. But how can somebody craft and build experiences that are hospitable, that are actually really connecting to humans? I think that is the part that wasn't easy. I love that becoming a theme. And I think that's likely going to be the theme throughout this show here.
Jessie Fischer: Definitely. And I've been talking to a lot of hoteliers and there's been a common agreement that you either have hospitality within you or you don't. And it's really difficult to train. I think it's one of those things — you've been in the hospitality industry, everyone is there and it makes you feel taken care of and thinks about things. And having been in many other industries, it is certainly not the norm.
Kin Sio: So speaking of hospitality, aside from the family business, you just mentioned short-term rentals as well. You are an Airbnb Superhost across quite a few vacation rentals. How does running that — it's probably a different scale from running hotels and all that, but still hospitality rentals, right? How does running that teach you about operational tasks as well?
Jessie Fischer: It's myself running guest operations, but behind me is a strong team. The maintenance team, the team on-site there when things go wrong in nature, as they inevitably do. So it's not just me, but I will say that just really brought me back to what's important.
Us in hospitality, we have the ability to shape how someone experiences a destination. And I think oftentimes it's maybe overlooked — the opportunity and privilege we have to let people have the best time that they remember their whole lives. And that's really incredible.
Kin Sio: Because at some point you had up to seven properties, right?
Jessie Fischer: Yes. Until we lost one from a wildfire in 2024.
[15:00]
Kin Sio: Yeah, which is part of the story of the development of GuestOS too, right? So back then managing seven, did you feel something where it felt manageable managing maybe one or two properties, but it just became completely unsustainable when you hit that seven mark?
Jessie Fischer: That's a great question. And this actually — I haven't thought about this before — but it's probably one of the things that made me realize that you can scale hospitality if you understand it at its core.
When I started, like anything, I think you should start with one thing, understand the process, and then expand. And so that's really what happened. I started with one property. Things went well. I learned through experiences, the best way to learn, and then continuously added on. And then of course, using technology — I used Hospitable as an early partner there, and they use AI at their core.
And that's really where I realized: wait, with seven, with twenty — it's that you have your systems in place and that you have really good data and information. I grew up around there. I've been to all those restaurants that I recommend. I've done the rock climbing or the whitewater rafting that I recommend to our guests. And so I think it's that quality and then having the systems already set in place. It's like every time someone wants to book, having the guide ready and not trying to do it every single time, because I did that for many years before I used Hospitable. And that's difficult to scale.
Kin Sio: Systems, right? And they're kind of getting you now building a very scalable system for many hoteliers. So I think it's a good segue into the birth of GuestOS. Before you even wrote a single line of code — you did lots of investigation, validation, talking to hoteliers. I think you probably talked to more than a hundred operators before you even built anything. Did you find from your personal experience, from other people's experience, there was a pattern that showed up — symptoms, not necessarily the core first-principles problems? What does that look like, from feedback to now building your hypothesis of building GuestOS?
Jessie Fischer: Yeah, well, two things that might surprise you from what you just said. One, I have never written a line of code. I just learn how to do things. And by the way, English is a new code language. But yeah, so that is one thing.
Another thing is I've always been super curious. I will research things and learn how to do whatever it is that I want to do. And I think that people now with access to information really can do that. It's so amazing.
And then also, I have not spoken to a hundred hotels. I didn't do much of that research ahead of time, because I really started GuestOS to solve an immediate problem for us and our hotel.
And it was the fact that most hotels, whether they're a small boutique hotel or a resort or over a thousand-room hotel, they all still work with similar back-end operations and face similar challenges. So I could be talking to a hotelier of 20 rooms and then one of a thousand, and we would be having the same challenges. And that's what was interesting to me. So I just started telling people what I was building and what we were working with. And then they said, "Wait, that's amazing. We need that." That's kind of how we have the network effect. And we still are referral only. We've gotten all of our customers today from just industry referrals.
[20:00]
Kin Sio: So from those experiences now, building the first version of GuestOS out of necessity — did you feel like that first version already nailed the problem pretty correctly? Or did you feel like over time there was some additional learning to continue tweaking to really get the right product-market fit that people are like, "Oh, seeing that work in action" — you can almost see the sparkle in their eyes that, yes, this is it. Did that moment happen on the first version or after some iterations?
Jessie Fischer: Yeah, I think the difficult part in the whole process was defining what we would work on. There are so many inefficiencies in hospitality operations that a lot of people want to tackle everything at once. And there is a lot of noise. There are a lot of options out there.
But what happens is on average, every hotel has between 10 to 15 technology platforms that they're using. And I was always using them myself or observing our front desk staff, and you have zero time to be going between these platforms. You're checking in guests, you're dealing with a bunch of things that come up. There's no time — you're not sitting at a computer all day just within the platform.
So I think understanding — the very first thing I did, you mentioned first principles — I wrote out exactly how the operations exist today, because you can only really fix something if you know how it exists today. And so I did that and then I removed — there's just way too much clutter — just removed a ton of things and went back to the basics. So that's why GuestOS is so simple. It's built for the staff to easily learn and use.
And then also something that's on our side is the timing in terms of the advancements in technology happening right now. The level of voice AI, how human it can feel, the multilingual abilities — that certainly is what brings the sparkle in the eyes and everyone is really excited. Because for the first time in history, we can actually shift hotels from being a place known for rooms to a place known for experiences. And rooms are just going to be one of those features that the hotel offers.
Kin Sio: Just in case we're not fully conveying what GuestOS really is, let me give it a take and you add on anything that I might have missed. So essentially, Jessie's team can really — and I saw this firsthand — build a phone AI agent that is actually friendly and knowledgeable, depending on how much knowledge you can fit to this agent. You can just launch really quickly. And then when your guest calls this number that is hooked up to this AI agent, they can ask about any questions you want this agent to answer, as long as you feed it the right information.
Getting to the point Jessie mentioned earlier — this is a subtraction of what the frontline staff has to deal with. It's not adding another tool but actually reducing their mind share of juggling 10 different tools and picking up the phone. It's one less thing that the staff has to worry about. And they know that the guest will be well taken care of with an AI teammate.
Jessie Fischer: Exactly. And I think that brings up — I love speaking in maxims — so one of my favorite ones is: beginners add and experts subtract. At this point, we know what brings real value that's measurable, and we know what's adding clutter, and people need to remove the clutter.
[25:00]
Kin Sio: So going back, you mentioned — I'm curious about the first deployment. When the first property went live with GuestOS, how did you see the operational shift happen in real time? Can you share that story? How did that look from a hotel's perspective?
Jessie Fischer: Yeah, I'm still so happy about this, and I think we're consistently seeing what's possible in hospitality. The teams — we win when the teams win. So we are there to support teams and to listen to them.
When we went live with Luma Hotel in San Francisco, beautiful boutique hotel, extremely tech-forward but maintains hospitality at the core — that deployment was exciting. And with every hotel, it's a little bit nerve-wracking. Our AI teammates are going out and they're helping guests immediately, and we're working with the top brands in the world, and every detail matters. So it's super imperative that that first interaction, which becomes our AI teammate, reflects their brand from the very start.
In the first 10 days, our AI teammate handles 30% of calls on average and just continues to get smarter and learn new capabilities that are mundane or repetitive. And now you're already seeing staff time free up so that they can actually carry out more of the in-person guest experience.
A lot of people talk about personalization. "Oh, now we'll be able to give everyone a cookie at check-in or whatever it is, and water." But that execution is incredibly hard. Friends would text me and say, "This hotel asked if I wanted water and a cookie right when I checked in. I said yes, and it never came." That's the issue. Ideas are easy. Execution is hard. And you have to free up time for your staff to do those things. Otherwise, you can't just keep adding tasks on top of what they're already doing because they don't have extra time. We're taking away the repetitive so that they can handle the execution of fun things.
Kin Sio: I can tell you how much of a difference it makes as a guest. Getting to the front desk and doing that check-in process — it's a night-and-day difference when you have a fully focused, attentive front desk or host, versus the situation I'm sure everybody has had: getting to the front desk, and before you get three sentences in, now the person has to pick up the phone, actually talking to somebody else, and then the person has to juggle the phone call and the person in front of you. Knowing that the staff wanted to give attention to what's in front of them, but at the same time, you don't want to upset somebody on the phone.
Jessie Fischer: It's bad for the staff, bad for the guests. And I think that really reduced situations like that.
Kin Sio: 100%. Every GM I speak to dreams of a world where the front desk — there are no phones. They're like, "I would tear out every phone at the front desk." Because it is true — during a check-in, you're no longer the main focus, and it's just not a great experience.
I'm sure before that first deployment, or with any hotelier adopting GuestOS for the first time, there's always that trend from being skeptical to "okay, let's try it out" to actually seeing how the magic happens. So what did the hoteliers usually say after the first month, after they see the system in action? What's the feedback you wouldn't see from the get-go during the sales pitch?
[30:00]
Jessie Fischer: Yeah, I think the biggest line of feedback we get is their team's approval. Because when I'm initially speaking to them, I'm speaking to the owners or the GMs. But then when we get the front desk approval — the operators who are in the system every day — that they start speaking about GuestOS and their assistant. They're like, "Oh yeah, I'll just tell my assistant." And they see it as a tool that can help them do these things. That's really why I built it. And I think that's the biggest compliment we could get back, because we're building for them. And if it's working for everyone, then that really means we're doing something good.
Kin Sio: That part is such a golden nugget that I think people overlook. It's always the GM or the owners or the operators who are making all of these tech decisions. And many times, I'm sure everybody will tell you, the boss or the owner signs up for all these new systems that the staff is not going to use. Or on the flip side, the owners will be like, "Why the heck is my team not using the tool? I spent all this money getting this tool and having people come in and do the training. Still, no one uses it."
I think the fact that naturally, when people start on the ground finding it useful and just start using it — it's a magical moment. Things are easy, there's no headache, everybody's happy when you build the product that is actually for the actual users. And I think in Silicon Valley, I'm sure you know a lot where to do the sales pitch, you've got to get the decision-maker buy-in, but not necessarily truly building something that the user would appreciate.
Jessie Fischer: Yeah, you completely nailed it there. I've lived that firsthand, and so seeing systems that we've tried — they seem really awesome and amazing — and then I think about the operations because I've also been at the front desk for a lot of my life. I'm like, "Okay, that's great in theory, but in execution, it's not going to work."
And so it does bring me — on weekends, I'll just be looking at all the action items being created by the front desk and completed, and it brings me a lot of joy. I'm like, yes, it's working. We really built a system so simple that they can just see how it works once and it's built into their operations today.
The path to simplicity is complex. This has been a crazy journey, but to build something that's simple and impactful and brings this value is exciting.
[35:00]
Kin Sio: Now that you have many hotels getting deployed and starting to use it — are there any assumptions, features, things that you knew that got invalidated by the users? And how did you change that?
Jessie Fischer: I think the biggest one — and maybe this is across all technology implementations — is that one thing can connect with everything, or should connect with everything. We focus on solving an immediate problem, which is all the FAQs and routing it to the right people, and getting that right first. Where I've had experiences where it's like, "Okay, but can you do every part of operations? Can you do maintenance? Can you do this?" I'm like, "No, and we don't want to."
We are highly focused on guest experience and execution of experiences, and staying super focused. But my brain definitely as a hotelier does all that too, so I get it.
Kin Sio: And it's a smart and not easy thing to do — being willing to stay in your lane and focus and not let the next shiny object take you on a detour. Because sometimes I tell hoteliers, we are all squirrels. We just all have that attention span.
Jessie Fischer: Wait, that's such a good point. And our engineering team hasn't been in the hospitality industry, but they're like, "Why is it so hard to get a GM on the phone? Are they busy?" And it's just — yes, we all know this, but it's hilarious.
Kin Sio: So it's great that now you have quite a few hotels under your belt. And obviously you're still doing lots of road shows, getting more hotels to adopt GuestOS. So now you're seeing two camps: the ones who adopted GuestOS and are seeing the positive impact, versus the ones that haven't. How does the daily operation of those two camps look different from what you see?
Jessie Fischer: Well, I think everyone who has been a hotelier understands things that people who have not will never understand. And so that immediately gives you a level of trust and understanding. As I mentioned earlier, we don't do cold sales. It's all been internal referrals because we are hoteliers building for hoteliers.
Our champions — people using it — they are excited and they're the ones telling other hoteliers about it. They're like, "You have to listen to this. You have to see this." And I think it's because we all care so much about this industry and that it maintains the human part of it. Our best advocates are our own customers. So it's really amazing.
That's actually why I built GuestOS — well, to solve those problems. And then I was demoing with companies that were attempting to solve those problems. And when I started demoing them, I was like, "No, this is so transactional. This cannot be the future of hospitality." So then I decided to build GuestOS, and here we are.
Kin Sio: For many hoteliers, adopting GuestOS and seeing what it can do — it opens their eyes and probably their minds too. When somebody starts seeing what's possible, what do you think changes about how hoteliers think about the whole business — not just the front desk, but what it means to use technology and AI to fundamentally change the business?
Jessie Fischer: That's a great question. And I've definitely had those conversations with chief revenue officers of large hospitality management companies who are overseeing a portfolio of hundreds of hotels. Immediately I just showed the demo and their brain is going — let's squirrel, like you said — in every direction. They're like, "This can help in so many ways." But I'm going to stay focused on the most immediate thing, which is the one we're solving now. But the expansion and potential to really have efficiency across the entire hotel operations is really exciting. We haven't had this technology available to be able to do this level of work before. So it's just a really exciting time for everyone, for hoteliers, for every part of the staff too.
Kin Sio: It's probably not well-known yet in the hospitality industry, but in the tech industry we all know — when people are still thinking about AI chatbots and all that, the next wave is already coming. We've seen OpenAI and Anthropic, how agentic workflows are starting to make a big scene in the industry right now. The next wave could be not just bot-to-human interactions anymore, but you could very soon get into bot-to-bot interactions too. So have you guys started thinking about what that could look like and how that could impact the whole hospitality experience?
[40:00]
Jessie Fischer: Yes, we are always thinking about the future, but also in the present. Doing what makes sense today to get us to what the future will be. And we already are actually having our AI teammates conversing with each other to handle and complete these repetitive tasks. We use them internally as well. So our efficiency for operations really has a lot of AI in the core operations there.
And then the people we hire on our team are excellent hospitality-focused people. And that's what matters, because we don't want to do the mundane, repetitive stuff. We want to focus on the people. And that's what we're building for.
Kin Sio: So I got one last question for you. Through this whole journey in hospitality, getting into tech, and now kind of coming back to hospitality — this career path — who has been your biggest champion throughout that process? And what's the best advice you've gotten from these people?
Jessie Fischer: Wow. Throughout my whole career. I think the core of it — my family has been the foundational source. And I blame and thank my family for the squirrel mindset. Always as an entrepreneur, growing up around that and seeing what's possible — it's just so amazing. Really just taking ideas to execution and finding out how — I love how Remy is making herself known in this.
But really, I remember growing up and always saying to my dad, "We should do this. We should execute all these things on-site." And it's like, "Okay, I do have a job. I'm a business owner. I have all these things." Ideas are easy. Execution is hard. So really just finally getting that.
And all these other layers — friends who say, "Oh, I want to buy a vacation home and manage it." I'm like, it is not a fun project. There's a lot of the admin stuff, the stuff with cities, permits. Oh man, I could get into it.
But I think the main thing that I learned is simple. It's just never give up, really. Life hits you with things left and right, unpredictable things. Building a business in nature is one of the most resilient things you can do — or one of the most things you can do to learn resilience — because things happen all the time, unpredictable. In a moment's notice, you have to evacuate your whole hotel from a wildfire or house people from a flood. And you don't complain, you just do the right thing and you take care of people. That's what I learned early on, and that's what I'll continue to do.
Kin Sio: Thanks for that piece of learning for everyone. Jessie, where can people learn more about you and GuestOS?
Jessie Fischer: I would say the easiest way is probably just LinkedIn, and reach out. I love connecting with hoteliers and other tourism folks. I'm on the Yosemite Tourism Board too, so I just love building that community, and I'm super excited for what's next.
Kin Sio: That's great. We'll make sure to put Jessie's LinkedIn profile in the show notes. We've been talking to Jessie Fischer, founder and CEO of GuestOS. Jessie, thank you very much for joining us.
Jessie Fischer: Thank you so much.
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