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Welcome to Travel Buddy
Join us for a fascinating conversation with Greg Ramey, Managing Director of BermudAir Holidays, and Jessica Steinberg, Travel Packaging Marketing Manager at Switchfly, as we explore the evolution of Bermuda’s flagship airline. Discover how BermudAir is enhancing the travel experience by combining local expertise with innovative packaging solutions and a commitment to exceptional service.
From debunking Bermuda Triangle myths to celebrating community milestones and uncovering the island’s unique business landscape, this episode offers rich insights and memorable stories for anyone curious about travel and transformation in the airline industry. Don’t miss this behind-the-scenes look at how Switchfly technology and effective teamwork with BermudAir are shaping Bermuda’s hospitality and future destinations.
Transcript
Brandon Giella (00:01.366)
Hello and welcome to another episode of the Travel Buddy Podcast presented by Switchfly. I have with me today a very special guest, Greg Raimi, the managing director of Bermudaire Holidays. Welcome Greg, thanks for being on the show.
Greg Ramey (00:16.642)
Thank you, Brandon. Happy to be here.
Brandon Giella (00:19.052)
And we also have today a returning guest, a fabulous guest, Jessica Steinberg, who is the travel packaging marketing manager for Switchfly. Thanks for being on the show again today.
Jessica Steinberg (00:29.307)
Yeah, thanks for having me.
Brandon Giella (00:31.126)
So today we are talking about Bermuda Air and how you guys have used loyalty and packaging services to enhance the way that this airline delivers great service, great airlines. But I have a question before we start, Greg. So how many people travel to Bermuda every year? I gotta know.
Greg Ramey (00:48.398)
Bring it.
Greg Ramey (00:55.182)
Oh my goodness, I should know the answer to that. I don't off the cuff. I can tell you there's 65,000 people that live in Bermuda and it's a very, you know, it's a population that travels quite a bit. The actual visitation is most certainly in the six figures, but I don't have the number off the cuff.
Brandon Giella (01:03.842)
Okay.
Brandon Giella (01:17.224)
Okay, okay, I'm just curious because I know that the Bermuda Triangle is a thing. Is that a myth? Just right off the bat, what's going on with that?
Greg Ramey (01:25.314)
So the Bermuda Triangle, what you need to understand is that Bermuda is an island surrounded by a reef system that when people were arriving by boat many, many years ago, did not understand the reef system and the rocks that go along with it. So there were many, many, many shipwrecks.
going to or from Bermuda, hence the Bermuda Triangle. It's now created this incredible scuba diving and snorkeling and reef system to explore. It's beautiful. That in itself is a reason to go down there. That's even just before you get to land. And it's really something.
Brandon Giella (01:50.594)
Okay.
Brandon Giella (02:06.43)
Okay, thank you for clarifying that for us because I'm sure there are many listeners that are tuning in and being like, should I even go? Because it's scary. It sounds dangerous.
Greg Ramey (02:12.97)
No, there is no danger in the Bermuda Triangle that you should be concerned about at all.
Brandon Giella (02:18.206)
Okay, good. I'm glad we got that out of the way. So now continuing on, Greg, tell us about your role with Bermuda Air and tell us about a little bit of the history of the airline and what you guys are up to these days.
Greg Ramey (02:31.544)
So when Bermuda first started, we had three gateway cities traveling to and from the US and Bermuda.
We're a pretty small, linear, or not linear, but we're a small organization, so we were all doing a little bit of everything. This is at that time. And I fielded so many phone calls of people who had just booked with us, who were about to book with us, that were looking for hotel recommendations, to the point where it became almost its own full-time job just being the hotel director. And just giving recommendations and feeding.
fielding just different criteria that people were looking for and trying to give a recommendation as best as I could. And it became pretty obvious very quickly that there was an opportunity for us to offer hotels along with our flights to create value for the customer, raise the average order value for us as an actual product and provide value to everyone involved. And so we started playing around with this heavily
manual in the sense of them and this was to the point where you know if somebody needed a hotel I could I could go out on their behalf and source different quotes from different hotels and go back and forth I mean each reservation was an extremely lengthy process and we went through that for a really extended period of time and so we ultimately decided hey look there's a product market fit here let's research how we can solve this and that's where we found Switchfly.
Brandon Giella (03:37.09)
Hmm.
Greg Ramey (04:03.39)
and know SwitchFly's work with other airlines was validation for us that hey this clearly works, it's scalable, let's see how we can make this work and we worked with the SwitchFly team from soup to nuts really creating what we have today and it's still in its infancy.
We're right now offering flight, hotel, and experience packages in Bermuda, now also in Anguilla, and then also in all of our gateway cities. So we fly to and fro Boston. You can book, if you're in Bermuda, you can book a flight and hotel package in Boston.
And this is just the tip of the iceberg. You mentioned loyalty before. We actually don't offer loyalty yet, but it's something we're exploring very, very seriously. And Switchfly has really been an enabler for us to really begin offering attachment rates and building out just what, you know, we're not just selling seats anymore, we're selling far beyond that. And Switchfly is the crux of that.
Brandon Giella (05:05.922)
Amazing, Okay, so for folks that may not be very aware of Bumid Air and the maybe history that you guys have or kind of like your destinations and your fleet and all that, like give us a little bit of an overview of the company so far.
Greg Ramey (05:20.398)
So we're Bermuda's airline. We're the flag carrying airline for the country of Bermuda. We fly to and from Bermuda and multiple cities in North America. So that's Canada and the United States. We fly Embraer 175 and Embraer 190 aircrafts. We're really, really proud of the service that we offer on board. We also serve all Bermuda products on board as well. And it's the customer experience that we really tout.
able to because of our size do a lot of things that larger airlines can't with regards to going above and beyond for the customer in the experience leading up to during and post travel and then from a business side just as well we were able to be nimble we can be quick
and just in general, we're like a really durable team. We have so much going on at all times. And it's really about what we can do for the country itself. It's something that we're all really proud of. Bermuda, the feedback loops are super, super fast because, you know, we all get coffee at some of the same places. We are all shopping at the same places. We are at the same restaurants. mean, we are there with our core user group and working towards
Brandon Giella (06:28.411)
Hahaha
Greg Ramey (06:37.622)
how to attract more people to the island. Tourism is a major, major piece of Bermuda's heartbeat. For those who don't know much about Bermuda, Bermuda is a insanely large financial and insurance hub.
It's actually considered the global risk capital of the world. so they, I don't know the actual numbers, but I've been told that 75 % of the Fortune 500 have their headquarters, their global headquarters in Bermuda. And so it's this huge amount of back and forth for board meetings and then for the insurance companies. then on top of all of that,
Brandon Giella (06:57.569)
What?
Brandon Giella (07:05.311)
What?
Greg Ramey (07:15.158)
is leisure. And so that's the flight and hotel packages and so forth. And so the population at large is constantly flying. It makes it incredibly unique compared to other countries that Bermuda gets compared to. And geographically, it's not even that close to, but Bermuda is constantly compared to the likes of the Caribbean and so forth. But Bermuda is actually 700 miles due east of the Carolinas in the States. And so it's in the Gulf Stream. So we get the beautiful pink beaches and the blue water.
Brandon Giella (07:39.294)
Mm-hmm. Mm-hmm.
Greg Ramey (07:44.942)
and some of that warm weather, but we're a long ways from Barbados.
Brandon Giella (07:50.774)
Huh, okay, yeah, so I knew where it was on a map, but I do associate it with the Caribbean. I don't know why. But now...
Greg Ramey (07:59.67)
It's the Beach Boys. Kokomo has just really...
Brandon Giella (08:03.298)
Okay, well this is before my time, Greg. I don't know the beach boys, okay. But I do actually know that song. Okay, so I just want to stop for a second because maybe other listeners know this, but this is a risk, what did you say? A risk capital.
Greg Ramey (08:06.654)
okay.
Greg Ramey (08:21.858)
Well, it's referred to as the global risk capital of the world. it's a huge hub of insurance and then something called reinsurance. So insurance companies get their own insurance and that's all done through Bermuda.
Brandon Giella (08:25.204)
I did not know this. Tell me about this. Why is this?
Brandon Giella (08:33.186)
Sure. Why Bermuda?
Greg Ramey (08:36.658)
I believe it happened in the 80s or 90s where the country put together, I'm going to get roasted for getting this a little bit wrong, but it's something to the tune of how they set these bylaws that really cater to the international business crowd. And then it's the insurance companies that came first.
Brandon Giella (08:46.447)
No, it's okay. We can look it up later.
Brandon Giella (09:00.118)
This is fascinating. Okay, I didn't know this. This is an SI. I'm sorry to everyone listening. But I'm, yeah, it's fascinating. Yeah, yeah, yeah.
Greg Ramey (09:04.108)
Well, what's really interesting is that everyone you run into is just on their way to Zurich, on their way to London, on their way to New York. It creates this insane amount of connectivity to the rest of the world that people just don't expect. It's got a very much a island vibe, but with a noticeable British touch, as well as North America.
Brandon Giella (09:16.844)
Cool.
Brandon Giella (09:25.61)
Interesting. Okay, so that's helpful about Bermuda itself. Tell us something that's unexpected about the airline, about Bermuda Air.
Greg Ramey (09:34.38)
Something that's unexpected.
You know, our...
Greg Ramey (09:48.076)
I would say that, well, you know, have a great story recently where one of our employees who is Bermudian just became the first commercial pilot in Bermuda's history. So he flies for Bermudaire, and his name's Tariq, he's a great gentleman, and he was working in our safety department originally and all this time has been working towards his pilot's license and he's now gotten the hours and he's flying.
commercial for us. We take a lot of pride in hiring locally and that comes through in our corporate side but as well as our cabin crew and now our pilots which is really exciting. I think that that's something that the company entirely is super super proud of.
Brandon Giella (10:25.344)
Amazing.
Brandon Giella (10:32.396)
That's cool, that's cool, amazing, amazing. Okay, so getting back on track a little bit more. So when you guys have decided that you needed to resolve this kind of hotel, I guess, recommendation engine problem, and then you guys, yes.
Greg Ramey (10:48.11)
You're being very polite, but yes, it was really me pulling my hair out.
Brandon Giella (10:54.142)
Yeah, sure. I can imagine. And so you found a good technology solution to resolve that bottleneck there. What's it been like since then? Now that Switchfly is a part of this packaging solution, have you seen any kind of dramatic effects one way or the other since then?
Greg Ramey (11:12.674)
Well, it's allowed us to promote this externally and really market it because it can scale. Previously, if we wanted to push holidays, was to me, was, no, I have to go through this. And it's allowed us to really seamlessly marry air inventory with hotel inventory and push that at mass. It's created an entire.
entirely new category for us, a new revenue stream, and one that can work while we sleep. There was hesitation with some of the hotel partners originally, because they knew we were doing this manually, and it allowed us to break through those barriers as well. We can scale with some of the larger properties on island. And it allows us to carry a bigger stick. We're not just getting people to the island, we're helping them decide where to go.
Brandon Giella (12:05.378)
Cool, yeah, I love that. Which has got to be huge for the hotels. It's got to be very, very helpful for them.
Greg Ramey (12:09.802)
Absolutely, we're the only real point of sale that's Bermuda based on the island. so, you know, other airlines are obviously servicing Bermuda from an air only perspective, then also a flight and hotel perspective. But I think there's a bit of a natural moat around Bermuda. And I think that most islands are like this. And the fact that we're inside that moat, we're on the island, we're friends with all these people, we can really make things move and shake a lot faster. And it really works for us instead of against us.
Brandon Giella (12:13.458)
Interesting. Interesting.
Brandon Giella (12:40.15)
Very cool, very cool. Well, Jessica, I'll bring you into the conversation here. I'd love to hear what your perspective or relationship to Bermudaire has been and if you're seeing any kind of similar effects across other airlines that have implemented this kind of technology.
Jessica Steinberg (12:54.693)
Yeah, for sure. Well, working with Greg and his team has been wonderful so far. And the one thing that I noticed immediately about their team that Greg kind of alluded to is because they're small, everyone's involved in almost everything, which honestly, from my perspective is wonderful. And they are so, so willing to try new things, which is.
So, so important in this space. Not every airline is going to have the same type of package customer and finding out who that package customer is can take a while. But in order to get there, you have to fail fast and try new things. And Greg and his team being so willing to try new placements, new initiatives, new even, you know, ways of saying things in their copy for marketing and things like that is going to be, I think, so integral to their success.
And we've already seen it, like, you know, him and I have worked together on a new placement that they have in their booking flow and things like that, that we've already seen success from, which is so, so exciting. But yeah, I think that in and of itself is huge, just their willingness to try new things. And from the airline perspective, being willing to offer something exclusive to these package customers. You know, like we talked about in our last episode, the onus is on the airline when they start offering packages, you know, why would a customer book it?
Hopefully you're giving them something extra that they can't get from Expedia, let's say. And Greg and his team are very willing to do things like that, which is really exciting.
Greg Ramey (14:16.684)
Yeah, and Brandon, just so you know, I've got Jess on Speed Dial. And so we're constantly trying to explore and experiment with different things. And Jess has been a huge asset in that. And at the very least, a sounding board to what maybe we should do or to, know, maybe we should try it a little bit differently. And Jess has been huge in that. so, so yeah, just to echo what she said.
Brandon Giella (14:16.706)
Cool.
Jessica Steinberg (14:20.411)
I'm sorry.
Brandon Giella (14:21.216)
Ha
Brandon Giella (14:40.066)
That's cool.
What I love about that story is, obviously, Switchfly being a technology solution, there's so many people behind it. And it is such a creative endeavor, if you will. And so you guys have this relationship that you've been working on and trying new things and trying creative solutions to different things. But also, Greg, like you mentioned, we see these people on the ground. We have relationships with these people. And so you're really using technology to build that bridge and make the connections between people and traveling and the joy that you get from traveling, the memories that you can
It's such a cool way to kind of present what I think you guys are doing, which sounds very tactical and technical, but it's really just creating a place for people to experience each other, which is really neat. That's cool.
Greg Ramey (15:25.462)
Absolutely. And trying to help them discover how close Bermuda is to North America. Everyone is always shocked when I tell them it's 90 minutes from Boston.
Brandon Giella (15:31.33)
700 miles.
Is that really? wow, okay. Yeah, okay. I didn't know that. Okay, so I'm in Texas. I'd be a few hour flight, I'd be three or four hours probably to get there. But if you're in Atlanta, know, Atlanta's a huge hub. It's gotta be what, two hours? Nothing.
Greg Ramey (15:38.21)
Just like this, Brandon. Yes, it really is.
Greg Ramey (15:51.859)
You know, Brandon, I can tell you that Texas comes up quite a bit inside the walls of tourism in Bermuda. I'm not gonna say Bermuda specifically, but tourism at large, Texas, hot topic.
Brandon Giella (15:56.45)
Okay.
Okay, okay. So you got a lot of Texans there, That's great. Very cool. So Greg, tell me what's next for Bermudaire? Where, let's say 2026, 2027, what are some things that you guys have on the horizon? Of course, no capturing any kind of company secrets or anything, but I'm just curious, where is your plane headed these days?
Greg Ramey (16:21.006)
Well...
It's no secret that beginning in December, we're going to be offering direct service from North America to Anguilla.
Which is really really exciting. We're gonna be going there from New York Boston and Baltimore Which is huge right now. There is non-stop service to Anguilla direct from Miami the American and so I can tell you that the likes of Anguilla are extremely excited about New non-stop service from the northeast and mid-atlantic. This has been hugely successful for us. We recently brought on more aircraft to our fleet to service Bermuda during
Brandon Giella (16:30.86)
Cool.
Brandon Giella (16:36.385)
Nice.
Greg Ramey (17:00.528)
the high and shoulder seasons. And in order to keep those planes flying, we're pointing them to Anguilla for the winter season. And this is something that we have already sort of earmarked as a success to date. And if this trend continues, we see other opportunities.
being raised down the road, but I'll leave it at that. But the Anguilla service is super exciting. We're continuing to fly to Bermuda year round from all of our gateways, but the Anguilla edition is great. We've learned a lot. I've now been to Anguilla. It's beautiful there. And it's a bit of a different animal than Bermuda. And so there's a lot of learning and education to be done, but I can tell you that the people are so, so great there. The beaches are beautiful. And so it's been a lot of fun.
Brandon Giella (17:49.3)
am Googling Anguilla now. Anguilla. Tell me about Anguilla. I don't know. I've never even heard of this.
Greg Ramey (17:54.878)
It's very close to St. Martin, which is a huge hub, but there's a ferry or another sector over air that you can take to get to Angola. creating the non-stop is a huge piece. It's typically a high-end traveler. The resorts there are second to none. It's really, really a premium product that they offer there. And it's small, similar to Bermuda. So it's not this...
Brandon Giella (17:58.05)
Cool.
Brandon Giella (18:07.682)
Ugh.
Brandon Giella (18:16.492)
Beautiful.
Greg Ramey (18:23.454)
overwhelming territory that we're taking on. And look, we haven't done, we don't begin service until December. So there's so much to learn until then. But it's something that we're really excited about. And again, it's an underserved market that we believe we can really, really breathe some life into.
Brandon Giella (18:38.818)
Cool, exciting. Maybe one day, nonstop from Fort Worth, Texas. We'll be there soon. Very excited. That's great, awesome. Okay, very cool. I'm excited about this. So launching in December, very neat.
Greg Ramey (18:43.884)
Look, nothing's impossible, Brandon. These planes can fly and land just about anywhere.
Greg Ramey (18:54.7)
Yes, and that'll go through May.
Brandon Giella (18:57.504)
Nice, okay, all right, get that spring season in, I love it. Okay, so any closing thoughts before I have some final questions for you? Tell us more about Bermuda.
Greg Ramey (19:06.574)
I can tell you that Bermuda is somewhere that's so close that everyone should go. I mentioned how kind the people are in Anguilla, but Bermuda is, it's tough to beat just the hospitality there. There's also an insane amount of history that anybody can appreciate. I would say that there's incredible food scene, boating and sailing.
the scuba diving, I'm still waiting to get PADI certified so I can go down there. But everything, it's just, it's a beautiful country. If you ever have an excuse to go there for business, you should take it and then otherwise find your own excuse and take your family there.
Brandon Giella (19:35.532)
haha
Brandon Giella (19:46.442)
Well, clearly if you're in insurance or risk capital, you should definitely go. This is the place to be. did not know this.
Greg Ramey (19:53.248)
Yes, definitely. I'm curious what these questions are. Bring it on.
Brandon Giella (19:57.662)
Yes, okay, so what is your favorite place you have ever traveled?
Greg Ramey (20:04.012)
My favorite place I've ever traveled, I recently went to Karuna, Sweden to see the Northern Lights and it was an old mining town. There's just not much going on up there and it was really simple, really cold and just beautiful and I had no idea what to expect and I've never taken a trip like that and I thought that that is right now my favorite place that I've traveled.
Brandon Giella (20:32.14)
Really? Interesting. Okay. I've never been up there before. That seems too far for me. I feel like I would freeze.
Greg Ramey (20:35.619)
It's you basically go to Stockholm and take another flight to the farthest north city.
Brandon Giella (20:41.768)
my gosh, I'd rather go to Bermuda, but maybe one day I'll get up there. Okay, next question, last question. Where are you traveling next?
Greg Ramey (20:45.228)
Hahaha
Greg Ramey (20:52.718)
So I travel quite a bit for work. So I'm gonna put a pin in that travel. I will say I am right now planning a honeymoon in Japan.
Brandon Giella (20:56.514)
Okay.
Brandon Giella (21:02.043)
wow, congrats, that's exciting. Very cool. I've heard great things about Japan. I've never been though.
Greg Ramey (21:04.962)
Yeah, thank you.
Greg Ramey (21:08.938)
I have never been either. I've been to Asia, but my now wife hasn't. And I can tell you that tea houses are very high on her list. I'm trying to fit in some skiing. I think that we're gonna be able to fit, we're gonna make everybody happy. But yeah, it's super exciting. And we're having Christmas in San Francisco. So we're kind of thinking we kind of stop there before or after to water down the lengths. And yeah, it should be good. That is also in its infancy of...
Brandon Giella (21:19.052)
Fair enough.
Brandon Giella (21:24.394)
Yeah. Cool.
Brandon Giella (21:29.61)
Cool.
Brandon Giella (21:37.562)
Fair enough.
Greg Ramey (21:38.816)
of everything. and you know what? There's one more thing I should have said that yesterday was Bermuda's second birthday. Our first flight was two years ago on September 1st. And it would have been in August, but there was a hurricane. so, first flight was September 1, and so we are, actually everybody that's on island right now is having a celebration at the office right now.
Brandon Giella (21:45.228)
Hey! Congrats! Wow!
Ha ha!
Brandon Giella (22:00.416)
Really? That is so cool. man, how neat.
Greg Ramey (22:01.932)
So yeah, we've come a long way since then and a lot of that is due to those feedback loops that I mentioned. We're right there with our customers and so we are taking every piece of feedback, good, bad or otherwise, and trying to make changes on the fly. And that's how we've gotten to where we are today. That's how we're working with the Lexus SwitchFly to offer packages and the loyalties down the road.
I want everyone to know that we hear you and we are constantly working to evolve and to grow and to create an airline that the country of Bermuda can be proud of.
Brandon Giella (22:39.968)
Amen, amen. Well, it seems like you guys are doing a great job and I'm really excited now to check out Bermuda. It hasn't been something that's been high on the list just for many different reasons. Bermuda Triangle notwithstanding. But I'm very excited. I should check this out now. So Greg, thank you so much. I'm excited to keep following your work and what you guys are doing at Bermuda Air. It seems really neat. And Jessica, thank you for joining and we'll catch you next time. All right, thanks guys.
Greg Ramey (22:51.888)
You have nothing to be afraid of.
Jessica Steinberg (23:04.089)
Yeah, thanks for having me.
Greg Ramey (23:06.638)
Thank you, Brandon. Jess always has a see you. I'm sure I'll call you 10 times before the end of the day.
Jessica Steinberg (23:07.611)
I'm Good to see you Greg.
Brandon Giella (23:10.722)
That's great. That's great. Alright, see you guys!
Greg Ramey (23:13.954)
Alright, take care guys.
Jessica Steinberg (23:15.291)
Bye.
