The Modern Hotelier #197: Staypineapple's Growth Strategy & Using Technology to Personalize the Guest Experience | with Michael Hirschler
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David M.: Welcome to The Modern Hotelier Hospitality's Most Engaged podcast. I'm David Millili. I'm Steve Carran. Steve, who are we interviewing today?

Steve: David, today we have a Mike Hirschler, Chief Growth Officer of Staypineapple in Staypineapple Chicago. Mike, thanks for sitting down with us. How you doing today?

Michael Hirschler: Great to be here. I'm doing great. Thank you.

David M.: So we wanna talk about brand growth. So tell us what is the state pineapple brand all about?

Michael Hirschler: Well, you know, it's not very difficult, sometimes we can make hospitality a little over complicated. Staypineapple is about great service, or as we like to call it, friend-style service. So it's about making people feel at home when they come here, and it's about providing a tremendous sleep experience from a product perspective, and it's about giving people a true sense of the neighborhood that they're staying in.

David M.: So what's the current growth expansion strategy right now for Staypineapple?

Michael Hirschler: Well, you know, we started as an owner operated company, and we grew to the 10 properties that we currently have. Um, but what we've discovered is we've got a. Kind of a secret sauce to what we do that's really unique and special. Our guests love us, and we've decided to take it on the road.

So we're expanding into licensing and management, uh, and we're going out there and we know that there are owners who are not interested in being part of the bland, that is the mega brands, um, that want something different, but they want the expertise, of a true management company and the special qualities that come along with a brand kind of our value add to them is we can take any building and turn it into a state pineapple, the one you're in is an example of that. It's how we grew as an owner operator, right? Being very, very opportunistic when it came to finding properties and markets we wanted to be in that allows us to be very, very flexible in what we take on from a management perspective.

David M.: So what are some of the B2B advantages about being part of state pineapple?

Michael Hirschler: I think there's a few things. One is the cost per key conversion is you're not gonna find anything better. You hear a lot about key money because people have to spend so much to become part of a mega-brand network. I mean, you hear numbers like 40, $50,000 a key just to meet brand standards. And it's like, okay, if you've got a great product out there. Why do you need to be doing that with us? You'd get our soft goods package, some of our branded items, you're part of the Staypineapple Family, as long as you've got a great product that you're looking at max $7,500 a key.

All of our technology is a hundred percent cloud-based, so you're not having to buy servers or new equipment. You just plug and play with what you've got already.

Steve: That's great, and I love that. Now we're gonna transition more to the technology side Sure. Of what you're doing at Staypineapple. And you said you brought up technology. Now, one thing that, you know, we talk about a lot is technology and AI almost replacing hospitality and humans. How does, how do you utilize technology to enhance the experience and not replace it with just technology?

Michael Hirschler: The last several months, all I hear about is ai, ai, ai, all of this. I want to say a swear word, but every conference I attend, and I've actually had the opportunity to speak on a couple of panels about this, and what we believe is in this day and age, in the post pandemic era, in an era in which, you know, as I've been sitting here, I think my phone's buzzed five times, right?

We're constantly in the face of our, the technology is in our face. You come to a hotel. To experience the human to human interaction. You don't come here to experience technology. So we believe technology and ai, were not anti AI at all, but that it should be a behind the scenes enhancement to the one-on-one interaction that our team members can have with you as a guest.

Steve: So expanding on that. You say you want to utilize the technology to enhance the guest experience. How are you doing that? What technologies are you utilizing? How are you utilizing them to create a better guest experience? You're gonna have to like, slow me down and stomp me because this gets me really excited.

Michael Hirschler: So, we started to enhance our tech stack, uh, prior to 2020. And we did that with two pieces of software. First was our RESERVA or RMS, the Duetto. We went out and we said, we're not gonna go get a hotel CRM. We're gonna grab Salesforce because it's the best piece of technology out there.

And that was what really got the gears turning in terms of do we just go with what is what everybody else does? 'cause it's the industry standard, or do we go out there and do we look at what's future forward and do we take the best piece of technology we possibly can for whatever that system might be.

And what we did is we took all of the rest of our tech and we completely ripped the bandaid off last year in 2024. It was painful. We suffered a little bit for it, but we replaced our property management system. We went with a brand new system called News, uh, which is relatively new here in North America.


But the way I've heard it, like in, you know, from our team members is it's like the iPhone of property management systems. And then we said, okay, wait a second. We want the two systems to be married together. So the PMS and the CRM, because the property management systems are inherently about the property and the product.

They're not about the guest, right? The guest is ancillary to everything else. Your CRM is what houses all the information on your guests. Those two have to have an equal standing in the relationship. And I don't know of any other hotel company that looks at it that way and what we're doing this year.

And we also did everything else alongside of it, all of the, the, you know, the bolt-ons. Um, because that's the great thing about Muse is they actually have a marketplace and they're all about open, um, you know, the open API integration. And so we then said, all right. Uh, what are we gonna do this year? This year?

It's taking that tech and it's leveraging it, and it's all about personalizing the guest experience and how do we start the relationship with the guests immediately after booking? And how do we then figure out how we can, once that relationship starts, how can we then personalize the experience on property? And then once they've left. How do we take the data that's sitting in our CRM and use that to speak directly to the guest and get them to direct book with us in the future?

Steve: I have a follow up question here. Is there any technology that maybe not, might not be out there yet, or something that you could see that could increase the guest experience or make a better guest experience, whether that's maybe enhancing a current system or maybe some technology totally different.

Michael Hirschler: Yeah, that's a good question. And it's so funny 'cause I think, tech has been so much a part of our psyche for the last couple of years, and then I'm so sick and tired of hearing about ai, you know, replacing all the humans elements in this. Uh, I'm like, no more technology, right? But I do think what, whatever, what I would like to see is what allows our team members at the front desk to have the easiest access to the data that is going to create the best possible interaction right now. Whatever interaction that is gonna be, whether that's check-in, whether that's questions being asked at, you know, during the, the stay, um, why the guest is here and, and having that in your face as an easy dashboard. Not complicated, and we're building it ourselves with our own in-house team.

We're working with our partners at Muse to, to do that. But anything, my whole philosophy this year is what limits friction. In the interaction between the team member and the guest, take away every single friction point you possibly can

David M.: For those who are listening or watching who are, you know, you talked about other brands and frustrations there. What are some of the financial benefits? About being part of state pineapple?

Michael Hirschler: Sure. I think, you know, we really are targeting that independent owner that maybe is, you know, a little bit burned out from, from having owner operated their right, their own properties, they might be somebody who has, you know, been toying with getting into one of these, boutique lifestyle brands that are underneath the umbrella of the mega brands. For us, it's a matter of saying you can maintain the independent identity of your hotel that you're so proud of, um, and get the backbone of a. Professional brand and management company whose senior leadership team has over 175 years of combined executive experience in all of the largest brands.

So we know what the best things are to bring and what to leave at the door, and you can feel comfortable that we're going to, ultimately, what matters most is not the rate, it's not the occupancy. It's your net operating income and that we are going to leverage all of our resources through our, uh, centralized, functional support through our distribution systems and the fact that we bring so much lower cost to operation. We're gonna bring a lot more to your bottom line.

David M.: Yeah. So we've, Jon, Steve and I, we're staying at the property. We've experienced it, but how does stay pineapple continue to drive high guest service scores?

Michael Hirschler: Starts with your people. I mean, and everybody says this. What's unique about my background is prior to this role, I actually spent 25 years on the human resources side of things.

And so I do actually believe, uh, what it is that I talk about, but you, you can't compromise and it's, it has nothing to do with the resume. And you know what the career background of somebody is. It's, do they have emotional intelligence, uh, and are they gonna be able to just treat humans as humans? And, and you know, it's that whole philosophy is if you were in the guest shoes, you know, what would you want out of the experience?

You know, it's that whole concept of always be thinking. You as somebody who lives here in our local, what. What can you offer? You have this vast, vast, you know, a treasure trove of knowledge that you can be sharing and imparting with our guests. They want to hear from you. They can read all the things that other people say.

They can, you know, read the TripAdvisor reviews for what to do, but there's nothing like getting it from the people that live here. So it starts with the people and then I think it really is about absolutely eliminating. All of the different layers of messaging that oftentimes occur and ensuring that whatever is being said at the top of the organization is flowing through directly to the line level team members, so that that way the entire organization is in alignment.

One of my favorite questions on our team member engagement survey, it surrounds, uh, a belief in mission, right? I, I feel like the work that I do is important to the mission of Stay pineapple. I'm not afraid to say this. I can guarantee at least 75 to 90% of our team members could not recite the mission statement for state pineapple, but they feel connected to a sense of purpose to what it is that that you know, that we are trying to achieve as an organization and to plus 90% as a response rate on that score. On that, on that question is, is just, it's outta this world.

David M.: That's great. Well, I appreciate it. That does it for another episode of The Modern Hotelier. This is where Mike, please let people know how they can get in touch with you, get in touch and find out more about Staypineapple?

Michael Hirschler: Sure, absolutely. You can simply go to our website and you can connect with us through our development page, at staypineapple.com

There's a contact us form, and be happy to talk to you about anything that, uh, anything that you want our input on. I think that's another important thing is we're happy to just give guidance and advice because we're relationship builders first and foremost. And we believe in the long-term, uh, you know, the long-term benefits of a relationship. So if anybody just has any kind of basic questions that they'd like to ask about hotel operations, we're here to start that conversation.

David M.: That's great. Well, that does it for another episode of The Modern Hotelier, hospitality's Most Engaged Podcast. Whether you're watching or listening. We appreciate you and we want to thank you Mike and the whole team here at State Pineapple Chicago for a great experience that we've had, and we hope to see you again soon. Well, thanks for joining us.