We need a super app for travel. TripActions thinks it can build it.

Nina Herold on the future of business travel, why you probably hate your travel and expenses system, and what it takes to do better.

Nina Herold on a wooden background.

Nina Herold is pretty sure business travel isn't gone for good.

Photo: TripActions

Nina Herold does not buy the idea that business travel isn't coming back post-pandemic. Even with more employees working remotely, even with Zoom and async creeping toward the mainstream, plenty of people will still get on planes, trains and highways to get the job done.

That doesn't mean business travel won't change, though. Herold, the chief product and operations officer at TripActions, thinks it might change a lot. Rather than travel for sales calls, employees might travel to quarterly team all-hands offsites; rather than a few people traveling constantly, everyone might travel a little. Most of all, Herold said, TripActions has found that a pandemic spent at home has made everyone rethink how, why and when they travel. And that there's a big market to be won in that transition.

Investors seem to agree: TripActions, which laid off nearly 300 people at the beginning of the pandemic, has since raised two huge funding rounds and is now valued at $7.25 billion, nearly doubling the company's valuation from two years ago. Boosted by huge growth and that massive pile of cash, TripActions is now set on an equally big goal: building the super app for travel.

Herold joined the Source Code podcast to talk about how travel is changing; what a travel super app might look like; why booking travel and filing expenses is still such a painful process; and why the difference between Basic Economy, Main Cabin, Economy Plus, Economy Comfort and Main Cabin Extra is such a tricky one to help users solve.

You can hear our full conversation on the latest episode of the Source Code podcast, or by clicking on the player above. Below are excerpts from our conversation, edited for length and clarity.

It seems like we've sort of inverted the way that business people travel. Instead of having an office that people leave and come back to, everybody flies together and then flies back apart again. And that makes me think, the number of people who travel, and what they want, and how they travel and what their preferences are, and the way that all this stuff works is going to change now, right? Before, I feel like the person who did quote-unquote capital-B Business travel was a very specific kind of person: You have your routines, you get Clear, you learn how to travel. And now we're gonna get a lot of people traveling a lot more who don't travel professionally. And I'd think that kind of person might want something very different from a platform like TripActions than the people who take 11 flights a month. Am I thinking about that the right way?

Yeah, absolutely. And I think that's where technology can step in, right? If you are someone who does not travel frequently, maybe you don't know to show up at the airport two hours early, or you don't know that there's multiple gates at the airport and it's important that you go to the right terminal. And so I think a really intuitive, user-friendly application — that is consumer-grade, that is on par with what you experience in your personal life — is imperative as we shift to this new type of traveler that we're going to see on the road, so that they don't need to do research ahead of time.

It's OK if they don't know the security lines and Clear and all this information, because an application can provide it to them, and the application can guide them not only through that booking experience, but through that on-trip experience as well. They can receive updates in real time, in one place, if their flight is delayed. And if they're using TripActions Liquid, they can easily expense everything having to do with that trip, because so much of the expenses we spend actually happen on a trip. Or they can push to other systems if they need to.

What is the totally idealized version of an experience like that? Is it like, I just type in the dates and where I'm going, and it just sort of, *poof* solves all my problems, and then it GPS guides me through my entire trip? Should this be totally automated at some point in the future? Or is there always going to be kind of a human aspect to it? When you think about the perfect version of a tool like this for people, what does it look like?

That's a really interesting question. I've thought a lot about this, I think it's more towards the former of what you said: We can use so much data and information to formulate a trip for you.

I would love to get to a point where you enter the dates and the times that you need to be there and TripActions kind of is your executive assistant that can just formulate the perfect trip for you. We know your travel habits from prior bookings, we know your loyalty information, we're able to sync to your calendar. And so we have all of the information, so that we can make the best decision for you, seamlessly, in real time. And that may change depending on the location or the time of day or the time of year. But we have all of that information to make the best decision for you.

How far away does that feel? Because a lot of the individual pieces that you just described are, if not possible, then at least plausible already. Does it seem like we're on the way to that thing?

Absolutely. So, if you run a search on our platform today, we provide flight recommendations in search results. We see over 90% of users select a search result from that first page. So we are close. We know what you're most likely to choose. And so it's just about, it's not how folks are used to shopping for travel. They're used to shopping for it piece by piece. And so it's about increasing your confidence in the technology that you're using, to be able to recommend what is truly the best experience, and what you would have chosen even if you had to scroll through pages and pages of search results.

And you can think about taking it beyond just your booking experience as well. What about if you're in the airport and your flight gets canceled? Can we proactively rebook you on a flight that we know would be your best option? Can we proactively book a hotel for you? And so I think the possibilities are endless. And we're definitely well on our way to be able to provide that seamless experience to users.

I've done interviews with travelers where they pull up their phone and show me their travel folder, and they have every airline application under the sun, they have their corporate booking tool, and they have a personal booking tool because if they can't find what they want they want to jump over to their consumer site. The behavior of using multiple different applications to manage travel is not new. And so we're just now making this relevant for business travelers and improving that experience, and making TripActions essentially the super app that aggregates all of that information into one place and helps you manage that experience.

Why do you think it's been such a long journey to make this system work for people? We've been on this "consumerization of business tools" grind for the better part of two decades now. But the stuff that you're thinking about and working on is so bad in most places. I've worked at very modern organizations where it was like from the 1970s trying to book a plane ticket. Why on earth is this industry so far behind?

One, it's complex, and it's a highly regulated industry. And two, it's inherently global, which makes it more complicated.

But if you think about some of the legacy providers out there in this space, there's no one that's providing both the technology and the service. And so there are travel management companies that have teams of agents — they have the relationships with the airlines. And they're the ones that previously, you were actually buying that airline ticket from. They're facilitating that transaction. But they're partnering with a technology company to provide the online booking solution. And so it provides that ability to kind of point fingers in either direction: If you're not having a good experience, it's really easy for the technology provider to say, "It's the service!" and if you complain to your service provider, they can point at the technology and say, "It's actually a technology problem!"

If you think about some of the legacy providers out there in this space, there's no one that's providing both the technology and the service.

When you bring those together, which is what we've done on the travel side — we are the online booking tool, the administrative platform that provides the ability to set policy and get real-time reporting, and we're also the licensed travel agency, we are providing that service, we have a team of global travel agents — you can provide a better experience. You can streamline your operations with technology, which at the end of the day is only going to provide a better experience for your user. That's where TripActions is really differentiated.

I'd also say, it took a lot of funding, right? You saw our news recently, we raised an additional $275 million for a 7.25 billion valuation. And so it took a lot of effort. But when you focus on the user and providing that user with a delightful experience, it gives you something to focus on. And so you know, it really allows you to solve the right problems.

I talked to someone several years ago who said that getting really good data from transportation companies, or inventory data for hotel chains, is really hard to do. And it makes it really hard to build automated systems that work. Has that gotten better over the years? Can you get the kind of information and data you want in order to do this stuff really well?

I think that kind of goes back to being both the technology provider and the service provider. You're the one that's building a relationship directly with the inventory providers, so you own that entire end-to-end experience, especially when you do it at a global scale. That's really where I've seen the problems come in with other providers, where you're aggregating information from so many different sources but also from so many different regions around the world, where you actually may be using disparate solutions.

The legacy providers are just building on top of that, and needing to pull the information from many different sources. When you have that one source of truth that is TripActions globally, we're able to provide that easily in real time. It's a huge differentiator in the market for sure. And it's extremely useful for travel admins and finance managers, who were previously waiting for weeks and months to get data and information to make better decisions. It's extremely useful to be able to get it in one place in real time. And you can pivot quickly.

And I'm guessing the only way to get that is just legwork, right? It's not like there's some beautiful database out there that you can tap into and solve all your problems. When you talk about needing a lot of funding and time to do it, is that the kind of stuff you're talking about?

Yeah! We have the beautiful database. We created it. We connected to all of these different sources. We're handling the transaction, so we make sure we store the right information that we can provide back to users. Previously, there was no one source of truth, no one beautiful database. But now that's us, both on the travel and expense side.

Previously, there was no one source of truth, no one beautiful database. But now that's us.

I'm really curious about the UI of booking, because on the consumer side, we've just decided how booking a flight should work. The lists are always the same, you can always filter them the same way. It kind of seems to work roughly the same with different colors no matter what platform you're on. Do you look at that and say, "OK, well, people like Kayak, so let's learn from Kayak?" Or do you go in and say, "How can we blow this up and try something new?"

Yes and no. A big change that we made a few years ago was actually building what we call the next-generation storefront. We built it because there's confusion, especially as airlines work to differentiate their products and are publishing branded fares, it became harder and harder to understand, airline by airline, what you were actually purchasing when you were selecting that ticket.

There's Economy and Basic Economy and Economy Plus and Comfort Plus and Economy Comfort.

Right. Even in the consumer world, you'll see some booking applications that haven't updated their model, where it's still just a laundry list of search results that you need to filter in order to find not only the flight, but the specific seat on the airplane that fits your needs.

So several years ago, we launched the next-generation storefront, which provides a grid style model for us to really stock the shelves, if you will, and allows users to easily understand what they're purchasing from each provider. It allows you to compare across two different airlines, different cabin classes, and understand how to compare like for like and shop for that. I think there will only be more and more opportunities to provide a differentiated shopping experience not only from what users experience with legacy business travel platforms, but what they're experiencing in the consumer world.

Earlier this year, we decided to have a personal travel offering as well. It's only available to travelers who are already on the platform for business travel purposes; it's called Lemonade. We discovered that the booking experience that we had created on the business side not only was better than other options travelers had for booking business, but it was also a superior experience to what you could get on consumer sites. There are aggregators out there where you can look at options across many different airlines, but you can't book and so then your itinerary actually lives in a different place. You're making your hotel booking in one place, your car booking another, your air booking another, and you're not actually aggregating that into one itinerary. But you get the benefit of things such as loyalty points, etc. So we took the best of both worlds, where you're able to earn your loyalty points as a personal traveler, but you're also booking it in one place.

You're making your hotel booking in one place, your car booking another, your air booking another, and you're not actually aggregating that into one itinerary.

Why keep that just to TripActions customers? Why not roll that out and try to just decimate the travel booking business?

For now, we have no plans to roll that out more broadly. It's definitely something that we see as a perk for customers on our platform. And that's where we're keeping it for now.

Fair enough. The other part of the UI question that's really interesting to me is the massive trust problem that you have when you book things. We've all just been trained to believe we're being lied to by all of these websites. There are hidden fees, the fares are different, everything's a scam. Especially as you try to build these more automated systems that work on your behalf, convincing people that you actually are doing right by them, in this system that has historically not done right by them, seems like a pretty interesting challenge. But maybe it's different when the people booking the travel are not necessarily the ones footing the bill?

The element of trust in business travel is actually extremely important. When we're building TripActions as a platform, we've always believed in providing that level of visibility and insight to the traveler when they're booking their trip. And so we're aggregating travel data and information and availability from many different sources, and we're presenting that to the traveler and giving them the information that they need to make the decision that is aligned with their company.

Is it easy to do that without giving people an endless set of knobs and buttons? To your point, there are a million ways to buy a plane ticket, right? I would think you could bury people in options to get the exact thing that they're looking for, or try to abstract all of that away at the risk of maybe not giving people the best possible thing for them. What is the right balance there?

It's easy to strike a pretty good balance here. Or, I would say, we've spent time fine-tuning and striking that right balance. Using AI and machine learning, we're able to present search results we know that are extremely relevant to the user. So we know information — whether it's their past booking behavior, it's their loyalty information, it's the booking behavior generally of their company or their co-workers — that we are able to use to influence the search results that we're showing them. And so maybe the first time or two you're using the platform, you don't have that trust, and you do want to scroll through.

But you'll quickly learn that while we have the breadth and depth of inventory in our platform, we know enough about you and your company and what you like to book that we're able to present those search results early on. So you don't need a ton of knobs and a ton of filters to get down to what you're looking for. But you can have trust, because if you would like to you can scroll through and look through all of those options, you can.

Fintech

Plaid is striking back after Stripe entered its core business

Onboarding customers through identity verification and ACH transfers is a hot sector in fintech, and the two fast-growing fintechs are set to battle it out.

Plaid is looking to help banks and fintech companies with anything related to the onboarding of a customer onto a financial product, said Plaid CTO Jean-Denis Greze.

Photo: Plaid

Plaid is moving into identity verification in a crucial expansion beyond its roots connecting banks and fintechs — a move that could put it in more direct competition with Stripe, another company known for its financial software tools.

In conjunction with its Plaid Forum customer conference this week, the company is also announcing two products focused on ACH transfers as it moves into payments.

Keep Reading Show less
Tomio Geron

Tomio Geron ( @tomiogeron) is a San Francisco-based reporter covering fintech. He was previously a reporter and editor at The Wall Street Journal, covering venture capital and startups. Before that, he worked as a staff writer at Forbes, covering social media and venture capital, and also edited the Midas List of top tech investors. He has also worked at newspapers covering crime, courts, health and other topics. He can be reached at tgeron@protocol.com or tgeron@protonmail.com.

Sponsored Content

Foursquare data story: leveraging location data for site selection

We take a closer look at points of interest and foot traffic patterns to demonstrate how location data can be leveraged to inform better site selecti­on strategies.

Imagine: You’re the leader of a real estate team at a restaurant brand looking to open a new location in Manhattan. You have two options you’re evaluating: one site in SoHo, and another site in the Flatiron neighborhood. Which do you choose?

Keep Reading Show less
Workplace

Getting reproductive benefits at work could be a privacy nightmare

A growing number of tech companies are extending abortion-related travel benefits. Given privacy and legal fears, will employees be too scared to use them?

How employers can implement and discuss reproductive benefits in a way that puts employees at ease.

Photo: Sigrid Gombert via Getty Images

It’s about to be a lot harder to get an abortion in the United States. For many, it’s already hard. The result is that employers, including large companies, are being called upon to fill the abortion care gap. The likelihood of a Roe v. Wade reversal was the push some needed to extend benefits, with Microsoft and Tesla announcing abortion-related travel reimbursements in recent weeks. But the privacy and legal risks facing people in need of abortions loom large. If people have reason to fear texting friends for abortion resources, will they really want to confide in their company?

An employee doesn’t have “much to worry about” when it comes to health privacy, said employee benefits consultant Jessica Du Bois. “The HR director or whoever's in charge of the benefits program is not going to be sharing that information.” Employers have a duty to protect employee health data under HIPAA and a variety of state laws. Companies with self-funded health plans — in other words, most large companies — can see every prescription and service an employee receives. But the data is deidentified.

Keep Reading Show less
Lizzy Lawrence

Lizzy Lawrence ( @LizzyLaw_) is a reporter at Protocol, covering tools and productivity in the workplace. She's a recent graduate of the University of Michigan, where she studied sociology and international studies. She served as editor in chief of The Michigan Daily, her school's independent newspaper. She's based in D.C., and can be reached at llawrence@protocol.com.

Enterprise

VMware CEO Raghu Raghuram: Edge is growing faster than cloud

The now-standalone company is staking its immediate future on the multicloud era of IT and hybrid work, while anticipating increased demand for edge-computing software.

VMware CEO Raghu Raghuram spoke with Protocol about the company's future.

Photo: VMware

Nearly a year into his tenure as CEO, Raghu Raghuram believes VMware is well-positioned for the third phase of its evolution, but acknowledges its product transformation still needs some work.

The company, which pioneered the hypervisor and expanded to virtualized networking and storage with its vSphere operating environment, now is helping customers navigate a distributed, multicloud world and hybrid work with newfound freedom as an independent company after being spun off from Dell Technologies last November.

Keep Reading Show less
Donna Goodison

Donna Goodison (@dgoodison) is Protocol's senior reporter focusing on enterprise infrastructure technology, from the 'Big 3' cloud computing providers to data centers. She previously covered the public cloud at CRN after 15 years as a business reporter for the Boston Herald. Based in Massachusetts, she also has worked as a Boston Globe freelancer, business reporter at the Boston Business Journal and real estate reporter at Banker & Tradesman after toiling at weekly newspapers.

Workplace

What’s wrong with current Big Tech HBCU partnerships

Big Tech is still trying to crack the code on hiring more Black workers despite years of partnerships with HBCUs.

Pictured is the first cohort in Accenture's Level Up program.

Photo: Accenture

As a business major at Prairie View A&M University in Prairie View, Texas, Sean Johnson had been on track to work in finance after graduating. But then his adviser mentioned a program that the historically Black university had with Accenture and Microsoft that was meant to function as a direct pipeline from Prairie View into roles in tech. It changed his entire career course.

Johnson had always had an interest in tech, and the prospect of being able to get a glimpse into the industry, as well as gain real, hands-on experience, appealed to him. By the end of the program, he had a full-time job offer at Accenture.

Keep Reading Show less
Amber Burton

Amber Burton (@amberbburton) is a reporter at Protocol. Previously, she covered personal finance and diversity in business at The Wall Street Journal. She earned an M.S. in Strategic Communications from Columbia University and B.A. in English and Journalism from Wake Forest University. She lives in North Carolina.

Latest Stories
Bulletins