Digital Transformation: Hyperpersonalization of Travel With Shane O’Flaherty | TNN23

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Episode Summary

Technology has changed almost everything about the way we live, from how we travel and navigate to the ways we share information and take photos. For those of you who are in your 20s (and older), I am sure you noticed significant differences in traveling in this day and age. Some things disappear, some things get invented. Modern technologies, smartphones and the internet mean tasks that once took days, weeks or months now happen instantly, at the press of a button or swipe of a screen. Being Microsoft’s Global Director of Travel, Transportation & Hospitality, Shane O’Flaherity is tasked to lead the technology that we enjoy today to make traveling easier and organized.


Hosts Andrew Jernigan and Allen Koski, together with Shane, shared their take on the AI technology that makes traveling a breeze. They talked about its numerous benefits for travelers who want to make the most of their time and the downsides of it when it comes to privacy. With many travellers already seeking a more customised and “local” experience, truly personalised trips via apps and websites are already beginning to take off. So take out your smartphones as you might want to book your next journey while listening to this episode of The New Nomad.

From the episode

Shane on Linkedin & Twitter


     Historic hotels in the USA: 

          The Broadmoor(Denver, Colorado)

          The Breakers (Palm Beach, Florida)

          The Greenbrier (White Sulphur Springs, West Virginia)


          Lanai, Hawaii (this is not your typical Hawaiian island, discover more)

What You’ll Learn


[3:24] There’s no school better than the Old School (or not?)

[7:48] AI assisted travel: the future of traveling

[10:52] My data is mine until I choose to share it

[17:11] On AI Big Brother-ing and privacy

[19:21] Meeting new people via micro communities

[23:09] Safety, security, and technology

Show Transcript


Welcome to The New Nomad podcast today. We have a really interesting guest today as we’re going to talk about travel and hospitality. Say- Shane O’Flaherity is going to join us from Microsoft, has a long career in you know, travel, hospitality and actually brings back some great memories as we’ve had some conversations about traveling around the United States, pretty much pre mobile phone technology, etc. I’ll be with my co-host, Andrew Jernigan, again, in on this journey today. Andrew, you remember those trips around the United States, perhaps with your parents are the first trips that you did, using perhaps the mobile travel guide and AAA TripTik, etc.?


Oh, yes, of course, and traveling, whether it’s Europe or other places, grabbing your notebook and jotting down, okay, I need to turn here. I need to watch for this building. And there’ll be a dog barking right there, usually at the corner turn or you print out MapQuest for those who may remember MapQuest you know, global business travel has really shifted, and, you know, the, the aspects of duty of care and and traveller check in and, you know, is the hotel certified, and there’s so many intricacies. But for those who are lifting it that those things may not be a concern. And we may just be thinking about Okay, is it Waze or Google Maps, Apple Maps, etc? How is it affecting us? Is it? Are we getting it through our watch? There’s all the sudden giving us the travel tips. Are we getting alerts in different formats? What’s our favourite app for it? It runs the gamut, doesn’t it, Allen?


Yeah, I mean, it just brings back memories of no joke, I used to travel with a roll of quarters, because you’d have to find a payphone at a gas station and say, I can’t find where I’m supposed to go. To find your office. You know, used to be you know, you used to learn how to use a map and decide which way is north, south, east or west relative to the map. Often, you did amble into some unique places that you didn’t expect. And it just brings to mind I did a ride a couple years back, that I left Germany, and we drove into Prague. And I had done the same ride 10 years earlier with my brother in law, this was before the technology, he was on the map. It took us hours to find the hotel. It was just, it was scary, was different. He had a watch for the trolley lines cutting across the roads. And then a couple years later, when you have right now in your car navigation, it was so easy. And I think that was really the underscoring the progress to me. So let’s bring Shane into the conversation. Because Shane, we you know, you you’ve had a you’ve seen probably more than anybody else, the move through this whole technology area, would love your perspective on how the technology is being used now and going but before then, why don’t you share with the, our audience, your background in this area? Because I think it’s extremely interesting how we’re moving forward in travel and hospitality.


Sure. And thanks, Allen. Thanks, Andrew. Appreciate the opportunity to join you. I mean, yeah, technology is just transforming the way we travel. And I remember going on sales calls in the early 90s printing out like the six appointments, I had the MapQuest for each appointment and trying to figure out a plan and how to get there. I remember travelling overseas, I live in Japan for a couple of years travel around China. And I remember thinking to myself, okay, I don’t have a cell phone, if something happens to me, no one will know. And I just had a backpack on. So those were the good old days, and it’s still are the good old days around travel. But it’s it’s constantly evolving. And I think you mentioned the mobile travel guide that was built in 1957 to help people, guide them around the country on where to dine and where to stay. And then you fast forward and then the creation of TripAdvisor. So it turned from like a professional inspector kind of opinion. Then it turned into consumer opinion. And and and now today, now you have social influencers who are like an next level of consumer opinions. But ultimately what we want as individuals and like when you read a book, or you read the mobile travel guide, or read now you read the Forbes Travel Guide, which it transformed into, you know, you’re trying to find the best place for you to stay that fits who you are your profile. So it’s more around this kind of hyper personalization. And then how does technology play into that and they talked about customer 360 and journey, probably for many, many years. 

But when you think of your travel even today, hotels do a good job of maybe marketing you before you show up. But once you arrive at the property from a digital perspective, it’s kind of a self service model. You know, are they providing you content to make your journey, a better journey, maybe a piece of paper that shows what’s happening in the hotel. But how do they how do we help this industry as a whole transform with technology, with the latest and greatest around cloud technology? I think Allen, you mentioned AI and machine learning, mixed reality there, you know, it’s decentralized it, it’s all coming. And it’s already here to stay. And I think, at this point in our lives, you know, in the past, we kind of had to adapt to technology. And now it’s kind of on the flip turn, where technology is actually adapting to us. And everything around, you know, if you think of anything around cognitive services around speech or translation, it has all reach human parity. So anything that we do, you know, technology can can blend into that arena in a very way that will enhance not only my journey, but then the employee journey, and then also kind of the operation. So we’re moving to a real time world, where, you know, the businesses are going to be more proactive with you to drive a better journey, whether that’s turned right here, stay at this hotel, see this dining establishment, as opposed to more of the world we lived in before, which is a little bit more reactive. So it’s fascinating.


And they’re proactive versus reactive approach. I mean, so important. And on the proactive side is the tools given to people now that helped keep them more safe, or find their type of food that they would like, or let them know, they’re in their proximity to some great things to visit. I mean, you’re right, the bespoke nature. I mean, to go back to like the mobile travel guide, he would just show you all the, you know, the first version, the one I remember from the 60s would show you the restaurants in the town. Now I go somewhere, I want Thai food that I can walk to, that’s open these hours, you go down the list, and it’s safe and anywhere in the hospitality side of things. I’m sure you want people to stay at the safe hotels that have a good track record, right cetera. I think that’s been a huge improvement. And I think the technology has helped with that. Maybe some of your comments about the bespoke nature of what people build for themselves with the tools that you and others provide.

Yeah, I mean, I think if you think of the past and from a human service, human human contact, it was all around provide at the high end of the market, anticipatory service to that consumer. So thinking ahead of what they may want. And now you know, you’re coming out of COVID, as well, you mentioned, security is an important part, and also health security. So no longer will I potentially, depends on you know how I feel, but I will have a more curated experience going into it. I will probably do a lot of pre planning, and I won’t maybe roam the streets as much as I did before. I want to ensure that hey, this establishment I walk into I’m comfortable from a health security perspective. So how does technology play into that? How does AI, what we call artificial intelligence, How does that AI assistant drive you down the journey to places that are an area that’s something you would love based on who you are and who your profile on but security, health security, as always, are paramount and become more paramount moving forward in the travellers journey?


So, you know, when you look at our right, we’re gonna have to edit this section out here. Good thing, we have producers who haven’t [inaudible]. Take it away Allen, I’m gonna mute and…


Question. I do have a question that ties in. We’ve worked with some groups that have come to Andrew and me. And they’re, they’re African American business travellers and personal travellers. And they’re, like, you know, in the, you know, we saw the movie Green Book, you know, we understand Green Book, you know, do you guys have any suggestions for us on good tools that we could have, that would provide direction tests around the world, for black-friendly businesses. And this, to me was a perfect example of the movement forward of digital technology, not just from the United States, but worldwide, that they were trying to put together hospitals, restaurants, hotels, other folks that they could feel comfortable sending folks to so I’m sure that you know, you working you’ve seen corporations wanting to slice and dice their populations differently. And obviously, populations raising their hand saying I want that. Help us understand, maybe even using that as a scenario, of how people can really bespoke, look at travel and hospitality, and feel comfortable using this technology.


Yeah, I think it all started said that. Again, it starts at the data layer and the data foundation on the bottom so it’s understanding who I am my interest in life, where I want to go? Where do I want to dine? What do I want to see? Where do I feel comfortable? From, from whatever parameters there are. So as more hotels, understand their customer and pull the data from all the different data silos that they have, and create a more holistic view of that person, and then map that with their hotels, and map that with restaurants, map that with other destinations, whatever it may be, what other establishment is, and then map that. So when I’m deciding on where I want to travel it using AI, it’s, it’s presenting me with options that are relevant to who I am, as opposed to the masses. So how do I create this kind of hyper personalization around who I am. 

And long term and if you think of where we are today, I mean, the consumer doesn’t really own their own data today. I mean, it’s, it’s owned by other tech giants, to a certain extent, but long term, I mean, our vision is what we call a decentralised ID, which essentially means that I own my data. Then GDPR, and Europe has done a really good job of this is I own my data, and I control it all. And then I create my own identity hub on who I am. And then I begin the process of saying, I’m only going to permission, this company into my world, this company into my world and this company into my world. So we’re going to do a value exchange with each other, where I’ll give them a little more information on who I am. And then they’ll provide more value to me during my stay, or whatever I’m doing my dining experiences. So we think long term over the next couple of years, the consumer is going to take back their world, take back their data. And then with that, then they can permission companies that that they love that they treasure that they have an emotional connection with, into their world. And then it begins a very, very, I would call it a kind of this next generation hyper personalization around the offering of where I’m going to go. And then secondarily, once I get there, how I’m treated, that will be very different long term. And that’s that’s our vision for it.


So, you know, it’s one of those things where technology is advancing at such high rates. And people are being inundated with more and more apps, more and more required software systems by their companies that, you know, there’s almost fatigue of, of the usage and the application of Where should we go for what which, and you’ve got to go to four different places, you’ve got to go to your your travel management portal, you’ve got to go to your all these different things to make sure you’ve checked everything. What is on the horizon, for innovation for adding all this up into one spot? Is there anything is anyone actually looking at how to how to build that all together and simplify the the the lifestyle of the global traveller, whether business travel leisure, or, you know, the retiree and remote worker?


Yeah, it’s a great question Andrew and I and we’re constantly thinking of it. And and really, it’s as the world is evolving, it’s moving to more of what I call an open data sharing model. Because as a consumer, all I want is this frictionless journey, get off my aeroplane jump in my car, see my hotel, I want the hotel to know that I’m arriving at a certain time. And but I want I kind of theoretically, I’d want them to exchange information across that data stream. So and that helps the consumer have a better journey. But then it also holds the hotel as example knowing that I’m leaving at 6am in the morning. Okay, let’s turn that room at 7am. So the world is moving towards theoretically kind of this common data model, we’d like it to go, where we’re exchanging information and understand private security concerns of the data. But I can exchange data in a useful way that provides a frictionless journey for the consumer and drives more operational efficiency. 

If you think of airlines and airports, do they share a lot of data? No, not really, should they? Absolutely, because I know they share more data than my journey at the airport is going to be a better journey. So I think long term we’re thinking around, you know, this frictionless travel journey. For the consumer, that’s more contactless, but then that means you have to share data across that stream. And as a consumer, I can share my data, but I want them to connect all those dots above. across that across that ecosystem and spectrum. So yes, that’s something we’re constantly thinking of the technology is there to make that happen today from a cloud perspective. But then how do we collectively as an industry move forward in that direction? You know, keeping the customer at the centre of the journey there that says, hey, this is what the customer wants? How do we how do we open our minds a little bit and move down this path in a way that protects the privacy data security of those individuals as well, and of our companies and our company’s data as well,


yeah, because it does require such an such interaction with the customer. Great to say, yes. These are the 45 programs I access. And yes, you can actually make them connect. Yes. You know, the API’s can talk, I give my permissions so that you can see where I’m staying. You can access Hilton, you can access enterprise, you can access National River car, etc, Europe car, wherever, and but it takes so much commitment from the user to actually allow this technology to exist. 


Yeah, I mean, it’s just the idea that, let’s say I put something on my calendar. Me, I don’t know, meeting in New York, or conference in New York is put on my calendar. Long term, what you essentially want is your AI agent. And we talked about this artificial intelligence enabled our AI agent enabled, that would say, hey, looks like you’re going to New York, can I book your airfare based on your profile, here’s what I would suggest. A hotel, here’s what I suggest, here’s your Uber lifts, or car or car service. So we want ultimately, the technology can help be more proactive in that journey, as opposed to me, like you said, going to a separate portal to open up, and then book x, book y and book z. But you know, I think you’ll you’ll see over the coming years that that AI can help enhance and be part of that anticipatory service for you as a as a traveller, whether for business or leisure, that can drive that kind of ambition for you and take some of the rudimentary stuff that you do, which is like maybe booking travel, you know, it’s like this AI enabled travel agency for lack of a better word of travel agent.


Yeah, it’s, it’s interesting, as we discussed this, where we’re trying to find the right hotel, the right place to eat, etc. But the thing I hear from a lot of our remote nomadic listeners is, they want to find people have like interests that that tie in. So maybe you comment on that in because there’s a push pull here, I have a lot of folks are like, well, I don’t want too much Big Brother, right. And I don’t want you know, that that know where they am all the time, I may turn off the geo positioning. But on the other hand, I have to explain them. Unless you have the geo positioning on and the AI technology, we’re not gonna be able to put together the person near you that you could meet with a similar interest. So maybe a little conversation for our audience, they’ll understand the push-pull. 


It’s a great conversation. And I think the industry that does it phenomenally well, and we’re going to step outside of travel. But I think the gaming industry does it quite well, which is in gaming, I’m talking about Xbox and PlayStation. So they create micro communities inside the game, and you have a group of people that are kicking, and then they create live events. So in game, they will say, Hey, we’re gonna bring on an old Marshmallow, which is a DJ, we’re gonna bring him into the event. And all of a sudden, you know, it’s it’s a tremendous growth in traffic. So when you think of a hotel as an example, I would if I, let’s say, I’m a whiskey taster, and I love whiskey, and all of a sudden, and I’m in a 220 room hotel. So there’s a couple, there’s two 300 people in that hotel, and they send a push message out and say, Hey, just FYI, the gentleman who’s gonna do a whiskey tasting in the next half an hour downstairs, and love for you to join, and it only goes out to the people who enjoy whiskey. So then all of a sudden, these groups come together of 5-10-8 people with like minded areas, you can pick pick, pick, pick your poison, as far as the the lifestyle event that you enjoy. 

But really, I mean, we think of travel. It’s really about community-centric approach. It’s about lifestyle, it’s about happiness, it’s about everything that you enjoy in life. But how do I bring a digital footprint to that and create these little micro communities. And for me, when I travel, I love meeting like minded people, as myself and new people and then more versed in the culture of the destination I’m at from a localization perspective, so it could be inside of the hotel. Or it could be Hey, we’re going to take a trip around the city to do a quick detour. Who’s in? And so you’re creating these kind of this, like these small, little communities in real time, like a flash mob, for lack of a better word. Yes, bad, maybe negative connotation. But but I do think Allen, this concept of micro communities around travel around interest around whatever, that’s that they’ve done a great job in the gaming space around that. So then how do you move this into kind of the traveling, instead have of having community managers that focus on what you said on TripAdvisor what you said on Twitter, which is more reactive.




How about having proactive community managers that set up these type of micro communities? You know, in different cities as an example?


Yeah, I mean, I would love that because as an example, I have a app called Untapped. I’m a guy who likes microbrew beer. And you can see who is what which breweries are the better ones in the area. But then you can even see who’s there, right. And then you go there and you’re like, Hey, Joe, you just is there, Joe here, you just posted a a perfect score in this beer. And it’s amazing. Obviously, when people, microbreweries, everybody seems to want to talk to everybody. It’s a very good, very good crowd to meet people. Or even the Bonvoy app that I use for our friends, you know, at Marriott. Some of the things that they push out as events, which you could either use points for, or you know, if you’re at a particular hotel. And that makes it so much more pleasurable, because obviously, when you when we used to travel by ourselves, there was nothing sadder than having a dinner or a drink at that table by yourself, when you see five other people having dinners and drinks by themselves, and one of those people might have the same interest. And I really appreciate what you said about just kind of pull that together. But it’s, it still seems to be reactive in nature, which is okay, but at least I still have that tool, right?

Yeah. And hopefully soon we can stand around a bar. But I mean, if you think of the design of hotels over the last five years, they’ve created various social environments in the lobby experience, which is fantastic. And then all of a sudden, COVID happened, and then that went away. So how do you bring back those social experience experiences that bring health security as a mindful subset of that as well, moving forward? But yeah, I mean, that’s, that’s essentially part of travel is meaning new people.


Yeah, and that’s when you’re living or spending extensive time overseas, finding that community, and when you’re outside the culture zone, culture, you know, you’re outside your comfort zone, is one of the biggest challenges, you know. It may come through the American Society of that city or inter nations or, you know, various formats. But, you know, technology has got to catch up with us so that it’s not just going to a social media group, or something to find, find the remote workers of that city or the expats in that city, because it’s, you know, right. Sure. We, we may use some apps but but technology has a lot to catch up with in the the globalised society that we’re in right now. Absolutely, absolutely.


Well, it to me, it’s comforting. I mean, one of the things that makes me really happy is when my children travel, or I travelled on our programmes, we have that panic button. You know, that’s geo position. And, you know, I feel like, not that I’m gonna put myself in more dangerous or unique situations, because we, you know, Shane Andrew, and we’ve all travelled to places pre phone that, you know, other folks might have said, I’m not so sure about, you know, your your trip there. But I do think it gives people a little more confidence to venture out. And that makes me really happy with technology that way. The problem is, we have a lot of folks that are very worried about geo positioning technology, as a big brother tool. And to me, I still look at as a safety tool. Maybe others disagree.

Yeah, I mean, I think as you as you travel, I mean, it was so mindful of safety, security, and, you know, and then how can technology blend into that? I mean, even think of into hotels, the hotel employees have safety buttons, to a certain extent. So, or that’s becoming some in certain states becoming a law, which, you know, again, we’re, how does safety security play into that when you travel? And the more comfortable I feel, when I travel, the kind of the broader I will go in that city. So yeah, I think it’s a great opportunity, having a tool like that as well.


So we ask all of our guests a really interesting question. I have a feeling you may have more than one answer, although it’s posited as one. You know, for the folks listening, please share with us like an overlooked person place experience that you would suggest our listeners discover. And if you’ve got a couple that are hot off the presses, so to speak, more than one would be fine to perfect.


I mean, I’m a big fan of us travel number one first and foremost. I’m a big fan of iconic old school hotels like the Broadmoor, the Breakers, the Greenbrier you know, historic type of hotels. Every city has one hotel, coupon theory have Elon, you know, and I love exploring the US and the nature associated with the US whether it’s down in southern Utah, whether you’re going up into Montana, so all of those I mean, tremendous. And then you sneak over into Hawaii. Lanai is one of my favourite islands. Absolutely gorgeous little boat trip off Maui that people forget about. I’m a big fan of I live in Japan for a couple of years. I’m a big fan of Asia if you’ve never been there. It’s an amazing, amazing place. I love Europe because I was born in Ireland, so that, you know. So the whole world I love I mean, and for me I live in Japan was such a unique place. Japan, China, whether it’s Shanghai, whether it’s Beijing, whether it’s Hong Kong, whether it’s 

Macau, Singapore. 

I mean, there’s the world there’s so many tremendous destinations around the world. And I think when you travel you you get a higher sense of awareness around culture and you kind of look at the world in a different lens than if you don’t travel. I mean, I think it’s critical to travel and, and I take my kids on a trip every other year to historical destination. I got five kids. So we did China one year, we did Italy one year, we did Ireland one year, and England. So I’m very, very mindful about how travel influences our lives. And it really brings about new experiences that we may never have in our life. So I’m a big, big, I could go on and on all day, and I my favourite hotels, and they have my favourite destinations. But it’s an endless journey. It’s like a you know, it’s like a race without a finish line, the travel world. I love it.


So where can people learn more about you to you? Do you use social media? And they should follow you there? Or you know, I’m sure some people have been intrigued with this. What’s the what’s the best way to locate you?


I’m on LinkedIn. Just Shane O’Flaherity, work for Microsoft, formerly at Forbes travel guide, mobile Travel Guide. At some point, I will create my own website that’s coming soon. But I do think that, yeah, I mean, we’re all about inspiring travel. And then we’re just high tech and high touch in high tech kind of come together moving forward. You know, and I think it’s, it’s a fascinating part of the journey and the evolution that the travel space is going. And if you think of what’s happened over the last year with COVID, I mean, the acceleration, you know, we’ve we’ve seen more digital transformation in the past year than probably we would have seen in the next 10 years. And that’s become extremely compressed. So over the next few years, you’ll see some of the fruits of the labour of what these large hotel, airline, travel companies have done. We’ll see the fruits of labour in the coming years, and it will be a very different experience when we travel, which is which is fantastic and all to the benefit of the traveller.


Okay, so everyone you are hearing from the Global Director of Travel, Transportation and Hospitality at Microsoft. So, Shane, you’ve provided some outstanding insights, spurred some thought. Thank you for joining us today. Thanks, my pleasure, and keep traveling.


So just to tie together, Andrew, what we’ve learned today, and I have to tip my hat to Shane on this, I’ve been to the Broadmoor of the Greenbrier and of course, the hotel DuPont, as I live in Delaware, all our amazing places. Actually the Greenbrier, if you do go there go visit where the US government was going to be taken if Washington was ever under attack during a nuclear war, all wonderful places. So I really feel the same excitement about the future of travel, knowing that tools are coming that are going to make it a lot easier. Andrew, final thoughts from you on what you learn today?


I am more motivated than ever, to build in the integration in the solutions that we deliver to our clients. You know, the AI is there so that when they land, they’re getting the Welcome to, you know, San Diego or wherever they’re landing. But so the traveller, check in all those things are built in, but there’s so much more needed. So as I hear this, I think collaborations are essential. So that the GDS, the all the other factors are integrated. And progress only happens through increased collaboration and cooperation. So that’s my biggest takeaway from today.


Fantastic. Great way to close. So thank you for joining us today. listeners. Remember the new nomads not just the podcast, it’s a community of people ideas, spirit, helping you take advantage of the location independent lifestyle, please check back again with us next week. And please look into us at or We love your reviews, keep on traveling. Cheers.

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About the Guest

Shane O’Flaherity is a global business executive and entrepreneur with a successful track record of leading his businesses and departments to their highest potential. His 25+ year career has been a catalyst for “Business Reinvention” — having excelled in moving industries forward through corporate leadership, strategy, venture capital, technology, customer experience, sales and marketing, operations, quality assurance and consulting. As Microsoft’s Global Director of Travel, Transportation & Hospitality, Shane has been leading innovation and driving digital transformation at leading travel and transportation industry companies to redefine their customer and employee journeys in addition to driving cost compression in their operations. He introduces underlying cloud technology Shane plays a leading role in driving the intelligent cloud and intelligent edge, with technology that utilizes artificial intelligence, predictive analytics, cognitive services, machine learning, blockchain, VR/MR/AR that are all focused on driving new business values and assisting clients.

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