From grad to VP: my journey to leading Skyscanner’s engineering teams globally
Andrew Phillips is VP of Engineering at Skyscanner, and joined the company as a grad back in 2009. He shares his career journey, the things he’s learned along the way and the best advice he’s received in making the big leaps to senior roles.
Andrew, you were probably Skyscanner’s OG grad, back in 2009. How did that happen?
I guess the story started years before I joined Skyscanner, back when I was 17. I taught myself a bit of coding, and worked for an oil company pre uni, doing a lot of data visualisation for oil wells and random jobs. It paid better than your average Saturday job, and it meant I could take five months to go travelling before starting my degree. It also helped me pay my way through uni, as I kept up my role there, doing 8h a week during term time, and more during the breaks. Fast forward four years and I came out of St Andrews Uni with a 2:1, a Computer Science degree and an intimate knowledge of the town’s many pubs.
At that stage I did a few of the grad recruitment rounds and my interest was piqued by two places. One was Skyscanner, this small start-up, no formal grad programme, a crazy idea born in a pub. They had this enormous ambition that belied the decidedly unglamorous office space they’d moved into (albeit it was a step up from cofounder Gareth’s spare room). The other was Dettica, part of GCHQ: on the surface, significantly more glamorous, offering a considerably better starting salary at that time, and also… enormous. I quickly realised I’d be this tiny cog in a massive machine, alongside 100 other grads. By contrast, I interviewed at Skyscanner, felt like I met every single person in the company, and realised I could make a far bigger impact, on something that people across the world use. I’d also been thinking about what I wanted out of the place I lived. I could either face a London commute or live in Edinburgh, a beautiful city with a massive international feel, heaps going on and easy access to green spaces. It felt a no-brainer.
I was far less savvy than grads these days. Had I taken a second to look at the accounts, I’d have noticed that they’d only just started to make a profit, and that they’d had to make five people redundant just a few months before. But I’m not sure that would have changed anything, to be honest. I immediately got this sense of passion and excitement, and knew it was where I wanted to be, that the culture was one I’d be able to grow and develop in.
Ok, so you join the company in an entry-level role in 2009, and by 2021 you’re leading an engineering org of over 600. What was your journey between those two points?
I started as a data acquisition developer, and was employee number 21. The majority were engineers. Three founders there too, one of whom, Gareth, had done the original coding — I always teased him I would never leave until I’d got rid of his last piece of code. In fact, the last piece of code Gareth suggested we change took down the site, so there was definitely some merit in my teasing.
In any case, my first day, everyone goes out to the pub at 5pm. I find myself chatting to Gareth, and one of the other founders, Bon. I happened to mention my dissertation at uni was in mobile app development, and we got talking about what a Skyscanner app would look like. Fast forward a year or so, and I was working to find a development partner to spin up a mobile app. That app, well, not the exact one, has now been downloaded over 100m times, across the globe. On day one I felt like I’d made an impact, just having that conversation that grew into a real, tangible offering before my eyes.
Over the next two years I built up a data acquisition team, we opened an office in Singapore and by 2011 I had gone, in two short years, from being the most junior in the business to managing a team of over 30. The pace was incredible, and it was kind of cool to be able to hire summer interns and have them come back during their uni breaks — just like I’d done with that oil company. Eventually, some of them were among our first grads.
A year later, I took on a data reporting product and our teams grew further. Then I moved into building a B2B product as a Director, into building the wider engineering org as a Senior Director, and finally now as a VP, leading our entire Engineering org.
Your career growth has been as accelerated as Skyscanner’s own growth. What’s the secret?
I’ve never actually tried to get promoted, and I’ve been fortunate to have managers that recognise the value of the work I was doing, who have given me opportunities to stretch. There’s also been an element of being in the right place at the right time. However, mid way through my journey at Skyscanner, our then Chief Operations Officer, Mark Logan, said something that was pretty instrumental to my having gotten to where I am now. The majority of my work had been in managing increasingly bigger teams within the data space. I was good at it, and so when I was presented with the opportunity to partner with another colleague on setting up our B2B offering, I wasn’t sure. Mark wisely said something along the lines of: ‘At the moment you’re a one-trick pony. Yes, you’ve excelled at the data side. But if you want to grow, if you ever want to be a leader, you’re going to have to demonstrate your portability. You’re going to have to take on different facets of this business and stretch yourself’. I followed his advice and pass a version of it on to the engineers I mentor: in short, demonstrate you have the ability to be a more senior, more strategic engineer by going outside of your comfort zone. Be bold and be curious.
Related, I have always had a bit of a personal mantra with work. I’ve always said, if I haven’t changed my role significantly every two years, if I ever stop learning, that’s when I’ll leave. It’s been 13 years and that’s yet to happen — that’s the beauty of Skyscanner. It’s also something I’m keen everyone within our engineering org ascribes to — we want every engineer to feel like they’re constantly learning and have the opportunity to change direction or jump into a new engineering area if they want to.
You had quite a big revelation when you made the jump into being an Engineering Manager too didn’t you? Tell us about that.
By 2013 I’d fallen into the trap I think a lot of engineers moving into management experience: you’ve grown a team, but you’re still far too involved in the development side of things. There’d be an outage and I’d desperately want to get my hands dirty trying to sort it. Eventually, my manager pulled me aside and gave me some invaluable advice that helped me make the next big leap in my career. As you progress up the ladder in Engineering — or indeed in any role — it isn’t sustainable for you to be into all the detail. You need to let your team fail. You need to let them fix problems by themselves, even if they’re doing it slower or differently to how you would. And you need to stop thinking that only coding equals impact.
This was a total gamechanger for me. It’s easier to see visual impact as a coder than your impact as a people manager. Instead, Engineering Managers need to see themselves as having impact as a multiplier of people. You can fix one thing at a time, or you can take steps that make everyone incrementally better. That’s very powerful. For a few years, I’d feel like an imposter if I wasn’t coding. The advice from that colleague meant I started to see I could make so much more of an organisation-wide impact growing other people.
Related, professional growth is such a big component of our Engineering culture. How do you contribute to it?
I’ve been really lucky across my time at Skyscanner, in that I’ve often co-ran projects or teams, or built them up with someone who’s had bags of potential whom I’ve mentored and coached with the aim of them taking over the running and management. A great example of this would be my colleague Wayne, who joined us as a Senior Engineer and is now an Engineering Director, who at the time was gearing up to lead our direct booking team. I spent a year running the team, with Wayne and I playing double act, building up his experience and confidence before he took the role on fully. Most recently, he as the student has become the teacher: he took the same approach in readying our colleague Manu to take over his leadership role there.
I really enjoy ‘building the bench’ and that’s essentially the most important role I can play as VP of Engineering. You build teams, build people and bring them along on the journey. Like I said, I’m no longer in the weeds of the details, and that is probably for the best: coaching, looking at people’s needs and development paths are my focus now.
We’ve an excellent programme around Internal Mobility that I’m very proud of: you can read more about it in Mhairi’s blog here, but essentially this is one of the best ways we help people develop in other technologies, domains or areas of interest. Now that I think about it, it’s a more formalised version of what I’ve done throughout my career here: I guess I’ve played guinea pig!
Lastly, a quick fire round….
….What’s special about Skyscanner’s culture?
We’re traveller-first through and through. We’re a company born of people who love to travel, we’re genuinely super users for our products and engage with them day in, day out. If we’re ever debating something, we ask a simple question — does it put the traveller using Skyscanner first? If the answer isn’t immediately ‘yes’, it doesn’t fly (no pun intended). A great example is those annoying pop ups that lead you to compare prices on other sites. We trialled these, making us millions ££. Our bottom line loved them; travellers hated them. Our competitors still use them, but we quickly scrapped them. That’s our culture at its core: do the right thing for the traveller, the money will come.
…Favourite read for someone looking to grow in an Engineering org?
When I joined Skyscanner, my knowledge and experience was centred around the oil company I’d worked for. It wasn’t process-heavy, but there were a lot of processes I didn’t like. Over time I realised that the right processes are key — but they should be simple, effective, and not a blocker to progress. In building out teams, that’s been a valuable lesson, and I usually start by asking “do we have a checklist for that” which feels like the right/lightest weight process to have. I’d recommend Atul Gawande’s Checklist Manifesto as reading for anyone interested in this area.
…Favourite benefit?
I’ve mentioned how travel is a passion for people at Skyscanner. I’m no different! So my favourite benefits are the ones that allow me to explore the world on my terms. We have an annual personal travel budget, which is very handy, and every five years you get five additional weeks paid leave on top of your normal holiday allowance at Skyscanner (there’s also a shorter, unpaid option at three years). I took my five weeks and added a week’s holiday on top for our honeymoon a few years back. We went to Australia to see family, Singapore, Sri Lanka and finished in the Maldives. It was a once-in-a-lifetime holiday and so special.
Related, we have a policy of being able to work from offices across the world. I love Singapore, so have spent time working in our office there, as well as our office in Shenzhen, China. Both are brilliant for satisfying my love for Asian cuisine. Closer to home, in a few weeks my wife, sons and I will be travelling to Barcelona, where I’ll spend some time in our office there, and then on to Marbella for a holiday. I love that I can balance my personal passions and family needs in this way (and also that no one bats an eyelid when said sons end up on my lap mid-Zooms!)
