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How Expedia is creating great checkout experiences using technology, leadership and innovation

In our latest Digital Lighthouse episode, Zoe Cunningham is joined by Liv Wild, engineering director of technology reservation checkout at Expedia.  We explore her role, the innovative changes happening at Expedia, how her team works and what leadership looks like for the future.

On the Digital Lighthouse, we get inspiration from tech leaders to help us to shine a light through turbulent times. We believe that if you have a lighthouse, you can harness the power of the storm. Digital Lighthouse is a mini-series of Techtalks brings you industry insights, opinions, features and interviews impacting the tech industry. Follow us to never miss an episode on SoundCloud now: See all the Digital Lighthouse interviews online for free on SoundCloud

 

Transcript

Zoe: 

Hello and welcome to the Digital Lighthouse. I’m Zoe Cunningham. On the Digital lighthouse, we get inspiration from tech leaders to help us to shine a light through turbulent times. We believe that if you have a lighthouse, you can harness the power of the storm. Today, I am super excited to welcome Liv Wild, who is the Engineering Director of Technology, Reservation Checkout at Expedia Group. Hello Liv and welcome to the Digital Lighthouse.

Liv: 

Hey Zoe. Thanks very much for having me.

Zoe: 

Can I start by asking you to tell us a bit about your current role and about Expedia Group?

Liv: 

So, my current role is looking after reservation checkout, which is three main responsibilities:

  1. We look after the checkout functionality for brand Expedia, which is expedia.com or expedia.co.uk checkout functionality,
  2. We’ve looked after the checkout functionality for Hotels.com, which is a separate brand within Expedia Group, and
  3. We’re also involved in the convergence of technologies that has occurred as a result of the recent changes that are taking place across the Expedia group for the checkout functionality.

Zoe: 

Right. So that’s like a tiny fraction of what’s being delivered in total by the Expedia group. For me, this is so much larger than what I’ve been exposed to in my engineering leadership roles. So, how is that structured within Expedia Group house? The whole total number of people working in tech, must be absolutely massive?

Liv: 

I think there are, there are thousands of engineers across Expedia Group.

In my team, there’s around about 60. And we are experts in checkout functionality, which is, of course, a really important part of the traveller journey, because Expedia Group covers around about 27 brands. We have a huge technology ecosystem.

One of the challenges that we’ve had to overcome, of the many in the past two years, has been to start converging those brands into a single technology platform, so that we can really focus on forcing simplicity within our technology choices. Previously, we have operated very much as single brands, and what we’re doing is converging in order to take advantage of the simplicity and the deduplication that we can get.

We do have specialists now in our teams, for example, they might specialise in checkout, then we have teams who are focusing on the convergence of brands onto a single technology platform. And then we also have teams who are building out that platform from an infrastructure perspective.

Zoe: 

For me, it actually highlights the challenge is even larger than I was envisioning, because I think there’s quite a lot of challenge just in if you were designing from scratch. As if you had the Expedia Group and the brands that are currently delivered by the Expedia Group, and you said, ‘Okay, let’s take a piece of paper, and we’ll design a tech team from from scratch’, right? How are we going to set people out to meet these challenges? That, to me, is a massive challenge in itself.

But actually, you’re not starting with a blank piece of paper, or you haven’t actually got the luxury of saying, ‘Oh, well, we’d have this person and this person would structure it this way. And we’d have written the code this way’. In fact, what you’ve got is moving from, presumably, what were separate independent systems before that now have to be converged together?

Liv: 

Yes. So, the convergence that we have is really moving from separate brands who are operating almost almost independently toward joining up to a single platform. It’s interesting that you say it will be more simple if we were starting from a blank page. It’s actually, from an engineering and leadership perspective, a really fascinating challenge to take the best of what existed before and then build on that, and help and support teams to move towards that new shared future.

Zoe: 

Right. Because, of course, you don’t just have a whole load of technical debt. You also have a whole load of technical solutions, right? And actually, it’s saying what have we got that can be reused or reshaped, rather than just ‘Oh my God, we’ve got to throw everything away and start again’.

Liv: 

Yeah. And there are a lot of engineers in our organisation who are experts and know how the current system works, and also how they would improve it. And here is an opportunity for us to really pick out those key parts that will help us to move forward together, and to address some of those things that, potentially, engineers have wanted to address for quite some time.

Zoe: 

I can hear your engineering leadership expertise coming through just in how you describe that because I think there’s a real art, isn’t there, to finding the positives in situations, and communicating that as well as communicating the challenges.

And actually, I think that’s such a clever way to put it to say: When there is a period of investment and change, that’s actually an opportunity for an individual developer or an individual team to suddenly bring out all the things that have been on addressable, I guess that have been not a priority, when you have a system that’s just carrying along as it is. Actually, now is the time to say, ‘Great, let’s put it all in the mix. And we’ll do the things that make the most sense’.

Liv: 

I fundamentally believe that innovation comes from constraint when we’re going through turbulent times. And Expedia Group isn’t just trying to do this convergence, we’re also coming out of the pandemic. Those constraints can be a really positive driver of innovation, because you have to decide which is the best way to solve the next problem. Usually, that information will be in somebody’s head. And it’s about finding that, helping the team build the confidence to put forward their suggestion, and then really get the team to focus behind the simplest solution to the next problem.

Zoe: 

Yes, so the phrase I’ve heard is creativity under constraints. I think that’s kind of what you’re talking about, that if it feels too open, it’s much harder to create, because there’s almost nothing to create off. If you say to someone, ‘we’ll build something’, how would you even know where to start?

Liv: 

That’s what I mean. It sometimes could feel if you think hypothetically about something. It would be nicer to build something from the ground up on a greenfield site.

But actually, because of the built up knowledge, and real understanding of what the boundaries are of the decisions that we have to make, that can force simplicity, and generate a lot more momentum behind the change that needs to happen. And I think over the past two years of the pandemic, at Expedia Group, there has been a real focus on forcing simplicity, reducing our cost base in a time when there were fewer people travelling. And that’s really helped engineers to think about, well, what are the best ways to solve these quite difficult problems of converging brands together?

Zoe: 

Yes, you say, engineers, and myself as a former engineer, you know, my first thought if I think technical team, I think engineers. Is your team, entirely engineers? And does that mean you have to work with other specialisms within like the whole Expedia Group technology team?

Liv: 

Yeah, so my team is entirely made up of engineers. But we work really closely with two other parts of the team, product and product managers who are setting the direction for the kind of experiences that we want to offer our customers, and then delivery, who were balancing that vision and that aim with the engineers capacity to match that aim, and to understand how we’re going to meet the deadlines. So we work in a real kind of triangulation partnership with product and delivery.

Zoe: 

So reservation checkout is the area and within that you have engineering and product and delivery. And you work together?

Liv: 

Yes.

Zoe: 

Does your engineering team within that then also have to link kind of sideways to other engineering teams in different areas of the business?

Liv: 

Yep. So, we have platform teams who are helping us with our infrastructure. So getting the best out of our infrastructure, for want of a better term, and making sure that it’s in the most secure architecture, making sure that it’s in the most modern architecture, and we’re getting the best out of it.

So, we work in partnership with our platform colleagues, we work in partnerships with other product development teams, because we are part of a customer journey. So we might be checkouts. But we need to work with other parts of the organisation who are building the rest of the customer journey.

And that might mean that we are working on other product aims and objectives in order to boost the capacity in other areas. Or it might mean just simply understanding the handoffs between those two areas.

And then for some of our more strategic projects, we have teams who were involved in working with people from across the organisation to help make sure that those programmes reflect both the customer journey, the entire customer journey, and also the perspectives of multiple parts of the organisation in order that the solutions can be really holistic.

Zoe: 

This is totally blowing my mind.

So, so far, we’re about 250 people, and when I joined we were nine people. So that’s kind of like my worldview of communicating within an organisation and we can obviously see how much more complex it is for 250 people versus now. This for me is like another level.

You must be spending all of your time communicating what you’re doing with other parts of the organisation so that you’re all in sync? Or do you have big things that get dropped or missed? Or do you have good processes for how to do it? I’m really intrigued by how how it all holds together.

Liv: 

I’m really inspired by our CEO. And yesterday, he published an article in the FT about his focus of the last two years. He became the CEO in February 2020, which was a brilliant time to become it.

It turns out, what really inspires me about him is that, it seems to me very clear that one of the things that he is passionate about, if that’s the right term is communication. He talks to us about what he wants us to do, and then also is comfortable to repeat that message in order to keep shifting the ship round to the new direction.

That’s also what he would like us to do with people so that we are reflecting that message down to people. So I think that within a large corporation, a large part of the leadership role in engineering is really honing that communication message about what the new direction is, why the new direction is and how what you’re doing.

Because it might seem like this very granular piece of code doesn’t relate to these big messages that are in the FT. But if you’re a manager, at my level, part of it is to really think about connecting that line of granular code to that larger vision in order to keep the momentum going towards that direction change that Peter Kern is attempting to get us to do.

Zoe: 

Fantastic. And so have you got any kind of particular tips or skills that you use for keeping your team on the page, you make it sound really easy. And I just know from experience that it is not that easy?

Liv: 

Oh, gosh, I hope I don’t make it sound easy. I think it’s about making sure that you potentially repeat a message to a point where one doesn’t feel comfortable anymore.

But actually understanding that sometimes the message needs repeating until it’s heard because people hear messages in different ways. And that doesn’t mean constantly saying the same thing.

The real lesson in my life that I’ve learned, I think is making sure that I’m not the only person saying the message. So working with other people to support the message, linking back to things that other people have said so that things that I say don’t just become libs, crazy idea.

They’re related always back to the organisational strategy. And really being comfortable about saying things, writing it down, slacking people, and making sure that the same message is repeated in slightly different ways. So that you are really thinking about how is this message going to land with different people who have different communication styles.

Zoe: 

So I really agree with this. And actually, I remember what you know, when I was managing director, I managed to get something that I said, which was ‘I’m always available, if you want to book a meeting with me’. It became a joke. There was an unofficial bingo sheet that was created during company meetings, and it made it onto the bingo sheet, you know, like ‘Will Zoe say this?’

And I was really pleased because I felt I had succeeded. And of course, there’s a difference between someone being able to repeat something and someone knowing that it’s true, but getting it repeated is kind of step one.

Liv: 

Yeah, and I don’t want to sound like I am just one note. You’re right, that communication has to be backed up with a demonstration of like activity around that message. It can’t be that my role is just to speak or just to alert people to what other people are saying. So I’m very engaged with my team and understanding what they’re doing, and making sure that what they’re achieving is in line with the objectives that we all have. And then amplifying back up to other people, when my team is achieving things that are related positively to the overall comms message.

So it isn’t just a thing that goes down, it’s a thing that also goes up and the repetition has to also be upwards. Because if you say to somebody, ‘my team has achieved X’, sometimes people don’t hear that until you’ve really battered the door down and got them to hear that the team has achieved X.

Zoe: 

Right. And that makes it, by being the kind of person who is forcefully championing everyone upwards. That’s what gives you the authority I suppose for want of a better word to communicate downwards.

Liv: 

Right.

Zoe: 

That’s what gives you the credibility to be able to lead people.

Liv: 

Yeah, and also, like I said before, it can’t just be me saying this message into my team.

So I have to work with other people that my peer group or within the team to get the message into the team. The same is true going up so it can’t just be me who represents my team and gets all the credit. I need to make sure that, part of it is around, sometimes forcing, which might seem a bit cruel, but certainly enabling people in my team to speak directly to people whose direction they are positively impacting.

Zoe: 

Yeah, you will take credit for your amazing work whether you want to or not. I love it. So I want to ask like, so since you joined Expedia Group in 2020. And now, what’s changed? So what was it like when you started and what is different now?

Liv: 

So the big changes that have happened are two.

One is the convergence of the brands. So when I started in 2019, we were all operating as single brands, almost in competition with each other, I think.

And in February 2020, Peter Kern joined as our CEO, and he changed the strategy. So he wanted to converge brands so that we were working and operating much more around the concept of an Expedia group customer journey, so that people would understand when they shopped with us that if it was Hotels.com, or Expedia Group, it was all part of the same family. So that change of strategy started to really be implemented in February 2020.

Zoe: 

So it’s actually quite interesting to me, because it feels from a technology perspective, like a big challenge, but obviously a good idea. Was it quite well received as a decision to converge the brands? Or was there kind of scepticism and pushback and challenge in that sense?

Liv: 

Well, this is where it comes in to the issue that arose in March 2020, of the pandemic, that obviously focused people’s minds because people stopped travelling. So we needed as an organisation to keep ourselves going, which meant to improve the efficiency of how we were operating, technically, really thinking about our cloud costs, for example.

And at the same time, Peter Kern was working with investment companies to make sure that we had sufficient investment to be able to continue. And I think what was brilliant about Peter Kent at that point was that he was clearly always very optimistic that travel was going to come back.

And so we had this dual challenge of converging the brands, that and the pandemic, but we had always this really optimistic CEO, who was always talking about that his positivity about travel returning, and that we would have an enormous part to play in it. If we adapted ourselves and use the opportunity of the pandemic to ignite that change that we have to make.

Zoe: 

Brilliant and come out of it stronger?

Liv: 

Yeah, definitely.

Zoe: 

So to sum up in a sentence, what have you learned? And how do you want to implement that going forwards? And how does that shape what you want to deliver and help your team deliver going forwards?

Liv: 

I’ve learnt that to going through this kind of change. I’ve worked in IT for 30 years. So it’s been changed throughout my entire career, this kind of change is really complex for people to navigate. And that one of the best things that you can do as a leader is to help people to navigate that complexity, to navigate their own change curves, and to walk by their sides and hold that ambiguity and that fear that they have, and that that takes time and investment, you really have to care about your engineering team in order to help them through it.

And I have always cared about my engineering teams that I’ve worked with. But this has been a brilliant opportunity to help me to understand how to really genuinely show that to different kinds of people.

Zoe: 

And how to double down on it, right?

Liv: 

Yep.

Zoe: 

So 30 years is a long time to build up all kinds of implicit knowledge, right? So I’m sure there’s a lot of things that you’re doing that are actually instinctual to you now, when maybe they weren’t when you started in your career, how much do you consciously change how you behave? So have you consciously changed things about your approach since say, 2020? And is there anywhere that you go to kind of learn new ideas and learn new approaches, in order to inspire other people to get the best out of themselves?

Liv: 

I’ve learned that you have to invest in yourself. And the best way that I’ve invested in myself is to really think about my behaviour and my preferences. So I want to be open about that with people. So when you say ‘have you changed?’, probably I haven’t changed since I was born at some level.

But what I have changed is that I’m prepared to talk about what it might feel like to work with me and to be open about some of the challenges that other people who’ve worked with me in the past have faced and to help people by sharing that, to let me know when they too are feeling these moments of friction so that we can deal with them before they happen.

And so I suppose if you were thinking about Brene Brown, I suppose that’s about bringing into work of vulnerability with boundaries. So sharing my own In preferences, my own challenges or weaknesses, as you might call them, and helping other people to navigate those in order that we can get to the best outcome for both of us.

And so I do quite a lot of work on really thinking about what my behavioural preferences are, and how to adapt those when it’s not working for the people who I’m working with.

Zoe: 

Hmm, that’s fantastic. And you’re also role modelling how to do that. So that when you’re asking your team to let you know what their preferences are, you’re actually showing that it is safe to be honest, and that you’re not just looking for a perfect answer of ‘I love to be in the office every minute of every day;.

And, you know, there’s no amount of work that isn’t too much. You know, I think it’s so easy for people not to realise that you’re genuinely interested in the honest answer when you ask this kind of questions. And actually, by being vulnerable, upfront and saying, you know, what, if you catch me at this time, I’m going to behave in this way. Let’s navigate that together. I think I think it’s fantastic.

Liv: 

And I hope it works. Because it’s all very well for me to sit on a podcast, isn’t it and say, ‘Oh, I do, I hope it works’. It doesn’t always work straight off the bat in this kind of really changing environment that we’re working in at the moment, there have been times where people who have really wanted to have a positive relationship with it hasn’t quite worked.

But being open with them about those challenges that we face together, in terms of how I have come across or what impact I’m having has helped me to rebuild relationships and to forge stronger connections. And I think that it’s in that forging those stronger connections and relationships, that you can much more successfully achieve the technical solutions, because what’s interesting about this conversation is I haven’t really talked about any technical solutions. I’ve talked a lot about how we have navigated the change that we’ve gone through through our relationships,

Zoe: 

Which is a fantastic lesson I think. If there’s one lesson from the podcast, it’s that relationships are more important when you’re a leader. Thank you so much Liv.

Just finally, what are your kind of aspirations or goals for you and for your team and for Expedia Group?

Liv: 

For Expedia group, the future is really bright. And today is a good time for us to be talking because Explore 2022, which is our annual conference about ‘these are the exciting things that we’re going to be offering for our customers’ is happening this week, and the company is full of really positive vibes about what’s happening in the future.

So we’re constantly looking for opportunities to remove the complexity. We want to make it easier to shop book and travel with Expedia Group. We want to see want to make it much more simple to see how to interact with our partner hotels and what they offer. We want to start to enable smaller travel organisations to use our services on their website. And we want to make sure that we’re enabling our engineers to be productive on day one.

So there’s loads of things that are going on in Expedia Group, and the technology is powering all of that. And it’s such an exciting place to work. I focus today on relationships, because I think that those changes that we need to make are going to be made through collaboration. And collaborating effectively is is like a really important part of what I think I’m adding to my team.

In particular, the aspiration that I have for my team, is to really lean into this change that’s taking place in our organisation, and to be able to have the confidence to collaborate effectively across those boundaries, and feel empowered to do what Peter Klein is telling us in his FT article, which is to make decisions and take risks and learn from the experience and keep going.

So one of the values that we have is to create a workplace where we’re proud to work. That’s a really important part for me that I really want to create an exceptional and inclusive workplace where people really do feel like I’m proud to work.

Zoe: 

Thank you so much for coming on the podcast and helping us to shine a light for others.

Liv: 

Thanks very much for having me.