Scaling Skyscanner, Part II: From Twelve to Twelve Hundred People

If you’re near the beginning of your startup journey, you shouldn’t be dreaming about achieving scale — you should be preparing for it. Shane Corstorphine was front and centre during Skyscanner’s rapid scale-up; here he talks about the importance of making ‘scale-readiness’ part of your business’s DNA

Skyscanner Marketing
8 min readApr 17, 2019
Achieving massive scale: the recently unveiled Statue of Unity in Gujarat, India

Skyscanner was founded by three friends who wanted to make it easy for travellers to find the best flights. Sixteen years later, Skyscanner has over twelve hundred employees in offices around the world, and serves eighty million travellers in fifty markets and thirty languages — each month! This post is the second in a series of blogs in which members of Skyscanner’s leadership team share the hard-won insights they’ve gleaned from their experiences — for the benefit of entrepreneurs and would-be entrepreneurs taking their own startup journeys. Haven’t read the first post of the series? Check it out here.

Scale is relevant to every single aspect of your start-up — from day one. It is a crucial, cultural mindset that needs to be embraced by every single employee — as much as it is the fundamental foundation for building a sustainable business.

Communication processes in a start-up can be relatively straightforward. Generally, everyone rolls their sleeves up and gets stuck in with any task that needs doing. As you are working in tens rather than hundreds, you can align more quickly to make key decisions. You might all head to the pub after work; the ideas roll, and decisions are made over a pint and, the next day, actioned. However, at scale, you need to try and move with that same speed — while growing your team and skillset and building products that need to be significantly more robust and scalable. It’s an incredibly challenging — and ongoing — job and it’s so important to get off on the right foot and that means thinking about growth early on in the vision and the strategy. Here are a few ways you can do this:

Create a structure that supports scale

At Skyscanner our approach to structuring ourselves was based on trying to recreate those conditions of our fast-moving start up days as we scaled to a company of hundreds. We opted for an agile structure, using the squads and tribes model first pioneered by Spotify. This structure met (and meets) our needs well; we created multi-disciplinary teams with between six and ten members, who were co-located and had a single goal to work towards. The goal may be purpose-led or directive, but it’s advisable to try and apply ‘growth metrics’ related to acquisition, activation or retention. These measures are often applied to the function of marketing, but product and engineering teams can often pull the biggest levers to impact these metrics.

This structure also allows for a series of ‘start-ups’ to operate at speed within Skyscanner while a series of central teams work on the underlying enablement (to ensure robust scaling). Decisions made may not always be the right ones, but this agile structure allows us to fail fast — which we are big advocates of here — in order to learn from our mistakes and quickly improve upon them. This structure nurtures the scale mindset we believe in here — more on that in a moment.

Get the basics right

We always spoke about having the hygiene of a listed business even when we were small. It focused the mind and pushed us to benchmark ourselves against ‘world class’ in everything we did. We’re still on that journey, but things like thinking in terms of risk, having good governance, the right advisors and internal controls and a culture of challenge really set an early pace which put us in an excellent position for larger funding rounds and our ultimate acquisition by Ctrip (when we were under more scrutiny). That may not sound sexy or entrepreneurial, but getting it right early has the potential to have as much impact on the success and ultimate value of your business as any product change or growth model. To paraphrase Mike Welsh, who built Blackcircles from nothing to its eventual sale to Michelin, you may question at the time why you do things like have a risk register and audit committee and independent challenging non-executives — but when you’re in a sale process, and questions are coming at you from all angles, you realise the value of doing all those things, because you’ve already thought about and planned for all of the hard questions.

Cultivating a growth mindset/culture from the offset

You need to accept from day one that the leaders you hire today may not necessarily be the leaders you need in two years’ time. Because of deeply embedded traditional ways of working and societal fixations with job titles, this can be one of the toughest things to explain to people and I am always very clear with companies I mentor that it is important for them to draw attention to this point early on in the recruitment stage. You may have a CTO who is absolutely superb at their job and can successfully manage twenty people. However, with the business scaling at pace, can he, or she, manage two hundred people in two years’ time? When the business is doing so well at such speed, there may be a requirement for a new skillset and for the person with that skillset to come in above the existing CTO. Of course, it is pretty natural to feel incredulous, annoyed, hurt, angry and unappreciated if a team member is brought in above you. However, there is another much more positive way to look at this: the company has done incredibly well, having actually grown at an unrealistic pace — and you have been an essential part of that scale story. You will forever have that on your CV and you will seriously impress at interviews when you describe how you grew the company from x to y. You are succeeding to the point where your development skills cannot keep up and you now have the opportunity to learn from someone world-class who has led at this level before. If people can park their ego, the opportunity to learn at a scale-up is constant and endless.

While it is key to be transparent about this — because, rather than careerists, you want to work with the kind of staff who have that growth mindset and get this from the start, it’s also worthwhile being careful with job titles in the early days. In a start-up when there are few people, there’s a tendency to hand out extraordinary job titles, assigning ‘chief’ roles early on. It’s worth avoiding this in case you do need to bring in someone new who can handle the increased scope at a later stage.

Thinking in terms of succession

Jobs completed by just one person in the early start-up days may be carried out by several people five years later. You always need to have one eye on optimising what you are doing now and an idea of how it might be done in the future so the transition can be achieved relatively smoothly.

Weekly town hall meetings allow Skyscanner to recreate the easy, frequent and effective conversations that powered the business in its early days. Pictured: Hamburg Town Hall, at night.

Keeping your CxO team visible and accessible

Here at Skyscanner we feel that it’s important for teams to hear from the CxO team on a frequent regular basis — we recreate the ease and frequency of those early start-up conversations with weekly town halls where anyone can ask questions. For teams to be able to improve, you need team mates who are at ease with challenging others across the business on a daily basis. This can be someone in their squad and it can equally be the CEO. We have had a very clearly defined culture at Skyscanner from the start based on transparency. We invite leaders to be challenged and called out if there is a belief that something is not being handled the right way, or if it could be better. And, it works both ways, of course; we believe in taking the time to give positive and personal feedback to team mates too.

‘Trust, but verify’

Another challenge as your company quickly scales from tens to hundreds is knowing what is going on. You used to be involved in every conversation and that’s just not possible anymore. It is crucial that you adjust to this change, as you cannot possibly follow all the threads of activity. This is what your effective structure is for — be it our agile route with squads and tribes or another route — and building a skilled team that can assume their responsibilities. Be comfortable giving people autonomy. Be clear on what the performance indicators are, empower them to do their job and check in regularly. As the Russian proverb goes, ‘trust, but verify.’

What we would have done differently at Skyscanner, had we known

We didn’t think through, and apply, some important communication structures early enough and that meant some of our basics were not in place. For example, we had a workforce of over 150 before we defined career competencies and this meant that, for career-focused people joining around this time, we weren’t being clear enough about where they sat in the business and where their journey for promotion here could take them. Similarly, we had a very generalist bonus structure that was based entirely on company performance and didn’t take into account individual merit.

Entrepreneurial mindsets a must

While the Skyscanner team may have grown to include more than 1200 amazing people, we’ve stayed true to our startup roots: we have worked hard to stay fast, agile, and when we fail, we fail forwards. Sixteen years after we were founded we’re still growing — if you’d like to help us soar even higher as we enter the next Skyscanner era, take a look at our open roles and get in touch. Entrepreneurial mindsets a must!

Check out our jobs site at www.skyscanner.net/jobs

About the author: Shane Corstorphine

Shane Corstorphine is SVP Growth at Skyscanner, the world’s travel search engine. Shane originally joined Skyscanner as Chief Financial Officer, where he was instrumental in multiple investment rounds, before becoming SVP of all regional marketing and playing a crucial role in making Skyscanner a truly global business.

Playing a pivotal role in growing Skyscanner from c.100 to 1,200 employees, Shane is also an advocate of the “fail fast” approach in the workplace and the importance of having a growth mindset. Having been an advisor to online startups for more than 15 years, and continuing to advise and invest in both start-ups and scale-ups, Shane is an enthused speaker on all things digital, including start-ups and scaling businesses for growth. In December 2018, Tech Nation published their new book ‘Upscale: What it takes to scale a startup by the people who have done it’ with journalist and author James Silver interviewing Shane exclusively for a chapter dedicated to overseas expansion.

Shane Corstorphine, SVP Growth at Skyscanner

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Skyscanner Marketing

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