Featuring Upside Travel
Read Time: 15 minutes
Welcome to Episode 44 of Students vs. Startups. This week, moderator John Gilroy talks with the Director of Growth and Product Leader of Upside Travel, Craig Zingerline. Upside Travel is the first online travel service built just for business travelers, where you’ll find the lowest prices and unparalleled customer service. Listen below to hear all about how Upside Travel is making planning and travel easier to manage for businesses!
If you would like to get weekly updates sent straight to your phone, you can subscribe below on iTunes!
Thanks to our Sponsor:
John Gilroy: Welcome to Students versus Startups Showdown Potomac. My name is John Gilroy. I’ll be your moderator today. Big round of applause here for show number 44. Wow! Got some people in the room here, yeah! Well, if you’ve listened to the previous podcast you know what’s going on here. We kind of took over a room at Eastern Foundry here in Rosslyn, Virginia. We’re at a table, one side of the table we normally have students, the other side of the table we have a startup. We have a blended approach today. One side of the table we have a student and a startup going against the startup. So this should be kind of interesting because all is fair in love and war and switching sides of the table is always interesting here. In fact, one of our students may be sitting on the startup side of the table in a few weeks as well, so who knows what’s going on here. So, let’s introduce our students first. First, I’ll start off with Obi. Obi, tell us about your background please.
Obi Ukaegbu: Yes, Obi Ukaegbu I am currently a Master’s of Technology Management student at Georgetown University. I come from a background in finance and technology specifically FinTech. I have worked as a technology analyst in the past. Currently, I am involved in the C-Suite of a blockchain cryptocurrency company, just past a major milestone in our project development pipeline and also capital contribution. So, excited to be here.
John Gilroy: In the classroom I assigned Obi a company called Elastico, which is blowing up. And low and behold one of my students came up to me and said, “Hey, can you connect me up with Elastico. I want to work there.” So, lots of people want to work for that company. That company is just really, really exciting. And, we have a student for a day. Our student for a day is Danny Jenkins, who is with Threat Locker. Danny, what’s it feel like to be a student for a day here?
Danny Jenkins: I don’t feel any younger.
John Gilroy: Well, you may feel younger when you hear some of the mottos of Craig’s company. Our startup today is called Upside Travel, and we have the Director of Growth here, his name is Craig Zingerline. Craig, how are you?
Craig Zingerline: I’m great. Thanks for having me.
John Gilroy: I went to your website, went to your LinkedIn profile. I see all these little catchphrases associated with your company. One is “business travel from mundane to magical.” Did you make that?
Craig Zingerline: I did not.
John Gilroy: Oh, come on. It sounds so good.
CraigZ ingerline: I kind of wish I had, though.
John Gilroy: Tell us about your background please.
Craig Zingerline: So I’m a serial entrepreneur. I’ve been a five-time founder. I’ve spent the past three and a half years actually in the Bay Area at two different early stage startups. Both had raised a little bit of money and took a great opportunity out here with Upside to hit up all things growth.
John Gilroy: Great, great, great. Now there’s also a motto that’s associated with your company that’s going to make the father in the room cringe, and the motto is “move fast and break things.” Is that good around your house, Danny? Move fast and break things?
Danny Jenkins: A lot of things get broken (laughs).
John Gilroy: So what’s this move fast and break things? What’s that all about Craig?
Craig Zingerline: My kids also do that (laughs). So you know our whole methodology is around not perfection but getting things out the door. Getting them in front of customers really early, so we can get feedback loops going and ultimately build a better product.
John Gilroy: Upside Travel, what business problem does that solve?
CraigZingerline: So the typical traveler who has to travel for work, doesn’t really have any tools at their disposal. There’s a whole bunch of companies set out for leisure travelers and making it slightly easier for them to book travel. But nobody is really focused on the challenge that business travel is, and so we’re focused exclusively on sort of the needs of those who travel for work, week in and week out.
Obi Ukaegbu: Perfect timing. I’m actually traveling to Portland tomorrow, from Wednesday to Saturday on work or mostly work. I’m flying business and I would like to know what are some of the competitive advantages of some of the search engines that may encompass some of the features that you offer as a company. I book through KAYAK, and then added my miles to Delta, and I’m flying business like I said. And I am offered a lot of benefits.
So booking through you, what are some of the competitive advantages compared to your competitors on that side?
Craig Zingerline: So I think primarily the number one key differentiator that we have is that we essentially have always done support. And so you don’t have to be a gold or platinum member of various programs to get support through us. So through all channels, email, phone, web chat, app chat, you can actually contact folks called navigators on our side who have basically the same level of access to inventory within the flights and hotel systems. That inventory level access. And for example, if your flight gets delayed, you probably already knew about that, but they’re going to promptly reach out to you to help to either re-book you, get you on something faster and a lot of times, will do that on the house.
And so we’ve really set out to … In addition to collecting your points and everything else that you can do, as a do-it-yourself booker, you can come on our site. You can quickly put together various packages or book flight only, hotel only if you want to. We’re competitive in terms of pricing. We also have some incentives around gift card savings. Essentially that when you book and you’re willing to take some small trade offs with your travel, for example, stay in a four star instead of a five-star hotel, you’ll get some money back in terms of … You’ll save your company money and you’ll also get some money back in gift cards.
John Gilroy: I would never go under five stars. How about you? (laughs)
Crosstalk: Never, never, never . .
John Gilroy: Danny, you’ve spent a lot of time on airplanes and falling asleep and having a bad back and everything else? What do you think of this proposal here?
Danny Jenkins: I think if you can make it easier and you can make it easier, then it’s extremely valuable. One of the big challenges I have, I travel a lot. I’ve lived in four different countries. I travel to Hong Kong to the UK to Ireland to Europe to Washington, D.C. every week at the moment, and it’s exhausting. It’s exhausting when my connection is missed. It’s exhausting when I get to the hotel and they tell me they can’t find my reservation. And I’m getting better at using the tools available to me. For the first time ever, I boarded the plane with my Apple Watch, which was nice not having to go through my bag. But I think the concept of making it easier is really good.
What I’m really interested in is how you deal with cancellations and how you deal with when the airline cancels on us and how you deal with what happens to the hotel booked after that and everything else?
CraigZingerline: Yeah, so typically if you’ve booked your travel through us, we will do whatever we can with our power to re-book you, deal with the change fees. So we’ve got different programs for different types of travelers as well. But your hotel is sold out and you need to move to a new one, instead of waiting on hold and getting a various sites to do it, our navigators will just do it for you behind the scenes.
So you basically give us your parameters, what you’re looking for, and we’ll handle all the rest, including the cancellations, the re-bookings, the changes, we’re really set out to save you time. So that when you’re stressed and you’re in the moment, you’ve got some backup.
Danny Jenkins: And how do we interact with you? Is it through an app or through a phone?
CraigZingerline: It’s through an app or through a phone or through email. Even if you want to, web chat. So we’ve opened up all the lines of communication. So it all comes into the same pool. The navigators are all trained on customer service and how to actually handle these types of disruptions. It’s really common. A large percentage of business travelers are impacted daily by these types of things, so that’s what we’re really well equipped to handle.
John Gilroy: So Obi gets on a plane and winds up in Hong Kong. It’s 2 o’clock in the morning and he’s got a headache, he can contact your company. You’re going to have someone there 24 hours a day, an actual human being that’s going to help him?
CraigZingerline: Yeah, it’s a human being.
John Gilroy: Oh, that’s not a bad deal.
Obi Ukaegbu: Not a bad deal at all. Something just popped up in my mind. You mentioned a native app that you also have, but it also seems that you have a web version-friendly app. What are some of the trade offs that you made, concerning app development as a company to choose whether or not you want to be fully native or also have a mobile web version.
Craig Zingerline: Yeah, so I think you have to look at the persona a bit of who’s buying. A lot of travelers still, in 2017, go to desktop to book. So out of the gates, we made a conscious decision to not go mobile only, for example, so that was off the table. I think there’s various trade offs that you can argue if you go mobile only.
Obi Ukaegbu: [inaudible 00:08:19] wise, are there are trade offs concerning having access to the web version, the URL, concerning actually using your native app?
Craig Zingerline: We can get to know you a little bit better through the native app. We can tell where you are, for example. So there’s just some things you can do in native from a features standpoint. I would say that we’re … The way we look at is that from an acquisition standpoint, really leaning on desktop because that’s kind of buyer behavior. It’s more desktop. But then from a value-wise standpoint, contextual content, alerts and notifications on delays and chat being available, those types of things are where our customers go to the app for.
And so we kind of bifurcate it in terms of is it acquisition or on-trip experience.
John Gilroy: I’m an old guy, old guy question: 1936, Woody Guthrie wrote a song called, “It’s All About the Do Re Mi.” Talks about the doe of the money. So I’m going to ask you the money question: So who pays for it? Does Obi pay for it? Does Danny pay for it? Where’s the margin there?
Craig Zingerline: Yeah, so the way the company makes money is actually on packaging various deals together. So if you book a flight and hotel, we’ve worked a massive number of deals with various providers to get you the best rates. So that’s essentially how we do it. It’s not dissimilar to how leisure competitors do it, but we’ve got pricing power with the packages and even with some of the single trip types that we have.
John Gilroy: So Danny, are you going to sign up before you walk out of here today?
Danny Jenkins: I’m going to ask a question about Southwest first.
John Gilroy: Ahh.
Danny Jenkins: I fly from Orlando to D.C. on Mondays with someone. It varies every week. But I inevitably end up flying home through Southwest. I love Expedia unless I have to call them and then I hate them, but they can’t book me home on Southwest and it’s really annoying that I can’t see my options for a flight home are. Do you deal with that?
Craig Zingerline: Yeah, so we don’t have Southwest yet. I would say keep an eye on it. We definitely show who the airlines are. We’re really transparent with that. In fact, we’ll 100 percent of the time show the flight info and airline and we’ll actually give you choices. So there’s nothing black box about what we’re doing.
Obi Ukaegbu: I did a search before I came here on Upside and I was very happy to see – sometimes you don’t see this with early startups – is popping up first in Google Ad Ranks. And so discoverability, how important is that for you as a startup and basically shorten that time for your customers, your target customers, to find out who you are in the mobile space?
Craig Zingerline: Yeah, that’s a really good question. So SEO is definitely a priority. The thing to keep in mind with our space is that the things that business travelers search for are very, very different than the things that a non-business traveler is going to search for in a lot of cases.
So there’s a ton of startups in the leisure, adventure space. Awesome things to do in various cities. But really when you get down to it, we’re more providing utility and so it’s actually been fairly challenging to figure out, from an SEO perspective, what are those things we should be focusing on. And I think we’ve done a pretty good job, especially as of late on coming up with the keywords and the keyword density, both on the SEO and SEM side. So we’ll also buy keywords to be competitive. So it’s a big factor, but we’re right now from a growth perspective, we’re looking at that and we’re saying, “OK, how much scale can we get from organic?” And I think kind of our native content and our topical content is really going to start resonating.
John Gilroy: Well, Craig, what I would do is I would sit down with Danny, get a tape recorder and have a top 50 questions. I mean, he’s the perfect candidate. He travels every single week. He’s a business traveler. He’s going to know a pressure. He’s a perfect target for you. Danny, do you got a question?
Danny Jenkins: I’m looking at your notes here and I’m curious how … You mention you can get your favorite rideshare. So when I fly up to D.C. on Monday. I always get an Uber from the airport and you click it coming to the door. It’s quicker than queuing up for a cab. How do you manage to coordinate … Are you tracking our location? How do you coordinate? At what point do you order the Uber?
Craig Zingerline: You can still order the Uber. But what we’re doing is we’re basically giving you credit within the system for Uber. And so if you package that up, you’ll actually save on that as percentage of your whole package purchased. But you’ll actually go to Uber and you’ll use the Uber app. We’ve also got rental car as well. We’re essentially what we’re trying to do is hit every component of the trip. Make sure we got a product there for you, so in the case of rideshare, it’s Uber. In the case of other car transport, it’s rental car options. But you would actually book that through Uber at the current moment.
Obi Ukaegbu: As a serial entrepreneur in this space, was there ever an experience that led to a catalyst for creating this company? Were you xxxx at the airline industry? What led to this coming to fruition for you?
Craig Zingerline: So I’m not one of the founders, but I will put the founder hat on for a minute. If you look at the founding team from our company, they have a lot of experience in the non-business travel space. Business travel was always seen as kind of the … It’s kind of its own frontier. It’s complicated and there’s different motivators and drivers. And there’s a lot of noise because there’s also all these big competitors with a lot of minute that are competing for visibility.
So the catalyst is really looking at it from a total adjustable market standpoint, saying, “Why is there nobody who’s focused really ever on this type of traveler?” They spend a ton of money, they spend a lot of time doing it. Business travel isn’t something that most people love to do, but you have to do it. Your boss says you have to be in San Francisco next week, you need to be in San Francisco next week.
So a lot of the catalyst came from a gaping hole in the market that had just never really been addressed.
Danny Jenkins: One of the big problems we have when finding hotels is finding a decent hotel with good business facilities, such as Internet that doesn’t smell. (laughs) I bounced around a few hotels here up in D.C. before I settled in where I’m actually going to stay for the next 10 weeks. Do you have any feedback in terms of what business travelers are saying? What is the incent like? I mean, Internet is huge in hotels. As a business traveler … As a home user, you probably don’t care, but when …
Craig Zingerline: Absolutely. It’s a good question. When we suck in all the hotel inventory that we have available, we’ve got various filters and algorithms that look at the key components of the trip that are most important to the business traveler. So that type of environment that you’re explaining would come up in our system as a best match or an Upside recommends type of inventory versus someone who’s in a leisure space. And they have the same filter capability, but they’re not going to push those results to the top because there’s other incentives that they’re probably working on. So we try to optimize for the traveler and look at those types of components within the search.
John Gilroy: Are there differentiations … For example, Obi is going to Portland for a few days and Danny here is going to be 10 weeks. Are there different personas you have to define the two different business travelers?
Craig Zingerline: Yeah, I mean, we’ve got the … We definitely have personas that we’ve developed and we’ve looked at and we’ve seen from our core audience. I think we’re still developing that. There’s the always-on-the-road frequent traveler and then there’s a whole bunch of people who travel to Florida five times a year, and so their needs do vary. We can service both right now. We can also service SMB travel coordinators, for example. We’ve got some hooks in that to make their life a little easier. We’ve got the ability to do multi traveler.
So there’s a whole bunch of stuff there that is kind of built on the personas. I would say we’re still in development, but we’ve spent a good amount of time actually from a data science perspective putting that together and looking at our … It’s really a cohort of existing customers, right? So those personas may change over time. Like our feature ideal customer may not be our existing customer, but we’re working that out.
John Gilroy: Washington, D.C. has 3,500 travel associations. About a third of those full-time meeting planners. It would seem to me that people who plan meetings for hundreds of … Every association in the world is here. And they’re booking rooms in Phoenix and Seattle and San Francisco and Las Vegas. Is that a target for you?
Craig Zingerline: It is, although a lot of the associations, especially as you get larger in size and this is true for businesses to is that they got essentially travel booking companies that they’re working with. And so, we’re specifically targeting the do-it-yourself business traveler who doesn’t …
John Gilroy: Right in front of you.
Craig Zingerline: Exactly. So that’s who we’re targeting currently.
Obi Ukaegbu: Do you ever find some of the issues of your B2B customers like the airlines, the hotels, the rental cars. And users might complain about … Like for me in the past, a huge issue of mine when traveling is when I don’t know that an extra bag that I bring on board is going to cost me $50 or $25 or $75. And a user, I can easily see them coming to you and complaining for that, “Well, why wasn’t this information displayed on your website?” Do you ever have those type of cross issues if you will for a lack of a better term?
Craig Zingerline: Yeah, so two things: One, we currently … We’re not serving basic economy. So you’re going to kind of bypass a lot of those issues, but although, we’re testing some of that feature set right now. On the second part, we really try to be proactive about communicating what those issues might be. And there’s a whole matrix of potential issues based on the provider. To the best of our ability, we’ll actually do the outreach the day before and the day of it says, “Hey, here’s what to look out for.” I wouldn’t say it’s 100 percent yet, but that’s really with are always on customer service and as we get more sophisticated in terms of our knowing our customers and knowing our supply, that’s 100 percent of the time, you’ll have an alert that says, “Here’s what to look out for.”
Even things like the weather. We’re currently sending out, “Pack an umbrella, it’s going to rain tomorrow in Seattle.” It’s a lot we can do …
John Gilroy: That’s every day, though, right?
Craig Zingerline: Yeah, bad example.
John Gilroy: That part of your website is built in. One last question from Danny. You’re the traveling man. You should be able to have 50 questions here.
Danny Jenkins: Every time I book a flight, I spend more time trying to get the right seat than I do getting the flight. Nothing makes me madder than sitting in the back row in the middle of two people. Do you have the option where you say, whenever I book a flight, get me – when I’m flying first class or business class – get me the closest seat to the front, in the aisle possible. Now, we understand that’s not always inside your control, but is there a feature that helps do that so that we don’t have to?
Craig Zingerline: Yeah, so what you’re talking about is essentially traveler profiles and preferences. We have some of that stuff behind the scenes. We haven’t exposed a lot of that to the end user yet, but we will be. The workaround right now is you can contact a navigator and give them your preference and in fact, they’ll reach out and ask what your preference is? “Mr. Jenkins, I saw you’re in the middle seat, would you prefer an aisle or a window?” And they’ll actually reach out and you say yes and they’ll say, “Hold for a couple seconds.” They’ll work their magic, come back and you’ve got a new seat, so it’s as easy as that.
Now, that assumes that there’s some availability, right? I don’t think we’re displacing other people, but when there’s an opportunity to do that, we do.
John Gilroy: We’re going to have to close it out here, but I have to tell the listeners that there is an Upside Travel engineering blog, and it’s probably one of the best blogs that I’ve read. It’s just the talent behind this gentleman here is really amazing. I think that’s probably why the company is so successful. If you follow the Twitter feed, you go to the website, you see what’s going on. They are really, really sensitive to this user experience. This UI, UX, you might as well have that on his business card because it really, really impress with … And their website is so simple. I mean, if you didn’t speak English, you can go to the website and figure out how to use it, so it’s a very user-friendly website.
Speaking of websites, how can they get more information on your company, Craig?
Craig Zingerline: Yeah, so if you go to Upside.com, you’ll see all about us and you’ll be able to book your travel. If you use the promo code ZING. Z-I-N-G. You’ll get a little something special. And if you follow us on Twitter, we’re Upside Travel, and I’m Craig@upside.com if you got questions or ideas.
John Gilroy: And Twitter is good because it talks about software development as well as travel. Well, we’re running out of time here, Craig. If you would like show notes, links or transcript, please visit the OakmontGroupLLC.com.
I’d like to thank our sponsor, The Radiant Group. If you are interested in getting involved in geo-spacial projects, contact The Radiant Group.
We are hosted by Eastern Foundry, a community of government contractors who are bringing innovative solutions to the government marketplace. For more information, go to Eastern-Foundry.com. If you would like to participate as a student or a startup, contact me, JohnGilroy@theoakmontgroupllc.com, and thanks for listening to Students vs. Startups showdown in the Potomac.