
Bobby Healy, CarTrawler
A seasoned tech investor and entrepreneur - and outspoken Google opponent - Bobby Healy has helped steer the technological vision of CarTrawler since joining in 2005.
For our November theme, PhocusWire talks to technology heads on the challenges of their roles and the rapid pace of change in travel technology and distribution.
What advice would you give to an experienced technologist from a different sector looking to come into travel?
For me, the very first thing I look at if I’m investing or mentoring companies, is to warn them not to get into B2C in any way and to not have a model that needs growth via paid search and competes with the giants [of the industry], because those are not investible businesses.
Second is, for a technologist, building a business in travel usually means sitting on top of a lot of legacy technology. There’s no way around that. For me anyway, the current exciting opportunity in the travel space is either tours and activities or in the dynamic packaging area.
With dynamic packaging, you’re putting flights and hotels together, so there are big technology challenges around connecting to disparate APIs. Those tend to be legacy systems or systems that are not able to scale up to internet conversion levels or performance requirements.
I say, don't start building until you learn properly of components in the travel industry, and, most importantly, talk to CTOs or architects who are already in the travel industry and understand the world before you start to build your product.
You should conceive the product around what’s technically achievable as opposed to what you’d like to promote to the consumer. That avoids a lot of heartache because I’ve seen numbers of businesses that started with super technology guys that built great proofs of concepts that had a really awesome consumer experience, but just weren’t implementable into the travel ecosystem.
That's kind of existential. If you get that wrong, you’ll never get a product that works for the consumer.
Website
https://www.cartrawler.com/ct/
CarTrawler works with many airlines. What are the technological challenges you have when trying to integrate with them?
That’s an easy one, and it’s not technical - it’s organizational. Think about a very large organization, which an airline is, and think about how small relatively the technology team is in that organization and how under-budgeted they tend to be just to serve their own needs.
As a third-party provider [like CarTrawler] that needs to get at least some work done on the airline side, it’s less about technology and more about, how do you influence giant companies to become great technology partners?
That's an absolutely key thing: You can build the best tech in the world and have the most beautiful product in the world, and the airline may really, really want your product, but they have their own timeframes and their own backlogs.
Without quoting names, we have airlines we signed 18 months ago that still are not live, and that's nothing to do with the technology. It’s just simply that non-air ancillary, which is our area, is low down on the pecking order compared to better seat selection and things like that.
My advice is: Make the technology so simple to integrate that it would embarrass the airline not to be able to integrate it. I don’t say it tongue in cheek because at our partner conference six months ago … we actually did a live integration on an airline app. We did it on the stage in front of everyone to show that it takes 60 seconds to do it.
It’s kind of a trick, but it helps politically when [airlines] get back to their home base and can talk about that.
Looking at mobile: What are other companies getting wrong when designing for mobile. and what is CarTrawler getting right?
The big thing everyone’s getting wrong - and I’m not going to embarrass people by naming them, but 90-plus percent of them get this wrong - is you have an app that has a good experience, and then you see that same app suddenly switching to a mobile web experience from a native experience just ad hoc.
Sometimes developers have to do things like that because you don't have the time or resources, but it’s just a bad experience. On most mobile phone networks, switching out of a native app to a mobile web experience adds 20 seconds of landing time. For anyone that hasn't been living a cave for the past 10 years, that means you’re going out of business in those 20 seconds.
That’s the number-one thing people get wrong: They simply under-invest in ambition levels on mobile. That's a really easy one to fix - it’s embarrassingly easy to fix. Instead of having one programmer, solve the problem and have two. It’s a predictable cost, and it means you’re not leaking all that business to better mobile players like Google, Facebook, Booking.com, wherever.
Does the mobile experience vary geographically?
It’s geographical for funny reasons. Some markets and regions are lucky they never had a desktop revolution. It sounds like the typical story everyone says, but we see it in the numbers.

You should conceive the product around what’s technically achievable as opposed to what you’d like to promote to the consumer.
Bobby Healy
You have certain markets that went immediately to mobile - Korea, China, Japan to an extent - and that means they think completely different.
The best parallel is if you look at Facebook. Facebook started off in the United States as a desktop product, and their mobile product is consequently pretty awful. It’s like a desktop product shoehorned into a mobile product.
If you look at China there’s WeChat, which is pretty much the same thing [as Facebook] only mobile. It actually captures 90% of a consumer’s activity in that one app, and the app is all they have.
The reason that happened is because people in China started on mobile and never knew what a desktop was or a laptop was.
I think about Skyscanner as a company that really got mobile right early on. In a sense they over-invested in it, and you could see that in their margins, and they've completely aced it. Unfortunately, most U.S. companies have gotten it pretty bad because they still see 60 to 70% of their traffic on desktop. It’s just funny: It’s kind of upside down to what you’d expect.
For our particular business, because we’re pure B2B, in essence we are later on in the device funnel. Because most of our airlines are still on desktop, we still see desktop traffic disproportionately to what the market sees. We have a funny problem to solve, but that's why we exist.
You've been a vocal critic of Google's strategy in travel, but do you admire about what Google does technically?
Taking my industry and investor cap off and putting on my consumer cap, they are absolutely awesome at consumer product and the notion of one company having all the data to support all the channels and applications. It is absolutely perfect, and they’ve executed beyond anybody I know - other than maybe WeChat or Tencent.
Plus Google Flights – it’s so much faster and so much better than all the other metasearch players. That's a great example of where they've taken a long-term approach to solving the problem. They made a large acquisition [in ITA Software] and they've invested in it, and they've not needed to go to the market overly early.
Therefore, they haven’t needed to quickly build something that then they get stuck with - in Ireland we say have you have shite on your shoe, and you’ll never get it off but you can still walk. What they did was for a long-term future.
If I put critic hat on: Because they’re a monopoly, they’re able to do that because they can wait as long as they want and let everyone grow and then simply take over the space. So that's my point - and actually Google Flights is the best product in the market - it’s now catching traffic by abusing the monopoly position that it has. It’s hot and cold; I’ll always get that dig in.
Do you think in general there will ever be a seamless traveler experience?
I think there can be, I just don't know how you do it without creating monopolies. In order to do seamless travel, you need to have seamless technology, and everyone needs to roll in the interest of the consumer with their approach. The things ahead of the actual fulfillment of the product are critical.

Make the technology so simple to integrate that it would embarrass the airline not to be able to integrate it.
Bobby Healy
When you have multiple competing companies, there’s never going to be a seamless traveler experience. Airlines are always going to want to direct the contact of their customers and so will hotels, so everyone will ultimately want to compete, which will actually create a monopoly.
Google is a good example of it. Unless you do that, you can’t have a seamless experience. Certainly Google can, and so could others, but Google could genuinely create the perfect travel experience. The problem is that would come at the expense of any innovation in the future outside of Google and also at a heavy, heavy cost to the industry.
The only way to achieve seamless is to monopolize the technology, and unfortunately I don't think long-term that's a viable solution, so therefore there will always be pain points.
What are some of your biggest challenges at CarTrawler?
Life at CarTrawler is a walk in the park where there are no challenges at all [laughs]. The biggest challenge is what I said earlier: Because we’re B2B, we’re not in complete control of the end result, and sometimes our partners don't move at the pace we’d like. That’s less of a technical challenge and more organizational.
Mobile has never been a challenge for us. We’ve always been ahead of the curve, or at least think we have. Because we’re a small company - we’re 600 people - it’s easy to organize yourself and point the guns in the right direction and make sure everyone is growing the same way.
Threats in the future more than current challenges would be more the way we look at the industry. You know what I think the threats are, I’ve said that enough. There’s nothing you can really do to engineer or strategize against that at the space we’re on. The threat to me is to our airline partners, not to us directly, because when you take away traffic from the airline partners, obviously we suffer as a result.
What emerging technologies will have the biggest impact on your business over the next decade?
Conversational - but less voice and more in the tech space, e-commerce. There’s a strong opportunity for us to mitigate the threat from the monopoly [Google].
When you think about how young people like to communicate - they don't like to talk, but they want to have a conversational experience, conversational booking. Therefore you’ll see bots, and we’ve done a lot of work with bots on the support side. But as that starts to modernize and as younger consumers start to become more frequent travelers, we’ll be able to shift traffic into conversational, which actually might bypass the monopoly.
How does that bypass the monopoly?
Because the experience is directly controlled by multiple providers. Instead of Google Assistant controlling everything, it could be WeChat, it could be Facebook Messenger; you break the stranglehold Google has.
Do you think CTOs in travel have the standing they should with CEOs, and do you see those partnerships as working effectively?
For me anyway, I’ve always seen a hybrid CTO/CEO. Similar to most CTOs I know, we have this spectrum disorder problem that makes it difficult for us to be CEOs.
The partnership between CTO and CEO is such a critical one because the CTO tends to be the creative innovator/implementer of strategy, whereas the CEO tends to be the pair of hands that steadies the ship when the CTO goes mad.
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In my experience, I’ve been lucky to have great CEO partnerships. With CarTrawler, that relationship has allowed the business to remain very flexible and adapt very quickly, like two football players knowing where each other is in the pitch without needing to look.
The CTO in a large organization is a different beast, where he or she tends to be - not in any disrespect - less in the room playing with the toys and instead doing the kind of sideline parts of the company that don't really drive it.
For a smaller company like the ones I’ve been part of, the CTO is a critical part of the innovation side. Other CTOs in the travel industry would be very similar in terms of makeup: largely responsible for setting the product strategy and getting it implemented and also evangelizing it, whereas the CEO would have more of an industrial scaling background and [be responsible with] building a huge team.
So it comes down to priorities and how to act on those priorities in any size organization.
Yeah, that's why the relationship thing is important, because for priorities - the CEO needs to trust the CTO to decide what’s important about things we should do, and the CTO needs to be able to trust the CEO when he says no. They need to be able to adapt around each other and form a joint strategy based on what we can do with the resources we have and what we should do.
I’ve seen very few cases where a technology guy is running the company, and I’ve never seen a case where a non-tech [CEO] was involved in strategy. You need both, and they’re two different people.