Shane Corstorphine CA: The 'failures' that lead to sky high success

Sky and plane
Andrea Murad By Andrea Murad, CA Today

14 May 2019

ICAS speaks with Shane Corstorphine CA, SVP Growth and former GM of Americas for Skyscanner, about entrepreneurialism, creating business opportunities, and mentoring startups.

You take a keen interest in up-and-coming entrepreneurs and startups. Which moments helped define your career?

The breadth of what I learned as part of the CA qualification is really exceptional, but I was only applying 15 to 20% of that knowledge while in audit at PwC. I felt the best place to use all that knowledge was by starting my own company, so I founded and operated an ecommerce business with a school friend – the experience was invaluable.

We eventually raised $250,000 to scale our business, but at that point, I thought that if we hit plan, I’d make some good money but wouldn’t know where my career would go. I was getting married and starting a family, and I didn’t want the uncertainty that comes with running a business.

Shane Corstorphine CASitting down and thinking about why I work was one of the best life lessons for me and I was lucky to have it at such a young age. The reasons for working will vary hugely for all people but it’s important to know and never to compromise for a sustained period of time.

The CA qualification gave me all these entrepreneurial skills, but it also gave me a safety net to be financially stable – as a result the more qualified I became, the more risk averse I become.

Stability for me and my family outranked being my own boss on my ‘why I work’ scale and the qualification meant I knew I could achieve stability without having to risk so much on running a start-up.

I offered the investor the chance to hire someone else, but they declined because they explained that they were investing in my partner and me – not the concept – so we returned the money and closed the site.

That was two years after starting it. A hard but invaluable two years of failing fast and learning quickly. Do I have regrets about making this choice? No. I’ve loved my career to date and stand by all the decisions I’ve made.

While I loved being an entrepreneur, I didn’t want the instability that comes with being a founder.

But I do sometimes think about what might have happened had I not made that decision.

I went into leveraged finance at RBS and moved to Barclays in 2008, where I eventually went into an operations role as a form of COO for Scotland and then the UK corporate team.

In 2006, I wrote a 10-year plan which I found recently. My plan had been to move from leveraged finance to private equity and then into a CFO role in a private equity backed company. Looking back, I was pretty close to this but in reality, I skipped the private equity step.

While I loved being an entrepreneur, I didn’t want the instability that comes with being a founder, so I found another way of working at a more established startup.

Even though I was in this operations role at Barclays, I continued to mentor online businesses in various ways.

Skyscanner was a relatively small company at that time, and they came in to pitch to the debt team that I used to be a part of, and the debt team talked to me about them – I said I wouldn’t touch them from a debt structuring point of view.

The next day, a colleague who was in that pitch and knew my background, told me their CFO was retiring and if I wanted, they could introduce me to the CEO. I thought about it for a few days, and then met with the CEO/founder for coffee.

I wasn’t looking, but if I hadn’t been mentoring companies and hadn’t invited that colleague to my sessions with investors and startups, he would have never known about my passion for these businesses.

How did you mentor startups?

I used to hold what I called ‘Tables for Ten’ to help startups raise money. I’d get 10 people around the table who wanted to do seed investing, like my colleague at Barclays, and invite three startups to tell their story. This was a hobby.

I wasn’t an investor myself, but I wanted to help ecommerce startups. I still mentor startups, but don’t do the ‘Tables for Ten’.

I started these in 2007 and 2008 when the market crashed because I had more time. I may have completed 10 deals in the 18 months leading up to the end of 2007. When I left RBS to move to Scotland and work at Barclays, I competed one deal in the next 18 months (end of 2009).

After the crash, I had more time on my hands and decided to spend that supporting a charity foundation – The Prince’s Trust – which allowed me to access start-ups quite quickly.

How did you find the time to mentor startups while holding positions that required long hours?

For six or seven years, I was working 12 to 16-hour days. Running your own business is brilliant fun, but it comes at a huge sacrifice – my friends were off having fun while I was working long hours.

I handed that check back because I made an informed decision that I wanted to de-risk my future financially, but I loved the accelerated learning and was happy to work the hours if it still allowed me to have impact, fail fast and learn fast.

What felt like failures or unnecessary steps at the time were integral to me becoming the CFO of Skyscanner.

I therefore took that work ethic with me when I went into leveraged finance. When that went flat, I used that extra energy to help startups and that led to the introduction to Skyscanner. I didn’t have the traditional experience as most CFOs, but the founder liked that I could speak to him in both financial and ecommerce metrics.

What felt like failures or unnecessary steps at the time were integral to me becoming the CFO of Skyscanner.

How have you seen the finance industry evolve over the course of your career with the impact of digital revolution?

Technology is doing an amazing job of disrupting any sort of marketplace. If you look at Amazon, Carousell in Singapore, or letgo in the US (run out of Barcelona), these are all marketplaces that had traditional ways of doing business before the internet and now, have been really disruptive.

Finance tends to be a marketplace of supply and demand – there are people who need money, and people who have money – and it’s only a matter of time until that gets disrupted.

Regulation will slow the pace of disruption, but I don’t think it’ll stop it. Depending on where you are in the funding cycle, we’re seeing crowdsourcing, increased liquidity, and as you move to the larger end of deals and financing, the two big issues are network, or access to people with money, and flow of information.

Investment banks probably still sit on the best black books in terms of funds that invest in the biggest IPOs, but the market’s becoming more fragmented and other players are rising in that investment bank community.

The flow of information is heavily regulated, but I can’t help but feel that it will become more liquid. For example, Quarterly updates could be more regular – all the information is there on a real time basis, so the need for a quarterly massive step change feels backwards.

How important is it to take the lead in changing times?

From a product and entrepreneurial point of view, even in large companies, there’s usually a cohort of about 10% of people that sees opportunities and drives and executes them. I like being in that cohort, but those who aren’t are also very valuable, whether that’s optimization, scaling or whatever that might be.

We are constantly rethinking, reinventing and rebuilding, even at the scale of a thousand people.

You have the creators who develop the ideas, and the drivers who see the ideas through, and then, when something must improve, someone else works on that.

At Skyscanner, we rip up and rebuild big chunks of our business every six to 12 months. We are constantly rethinking, reinventing and rebuilding, even at the scale of a thousand people. The process obviously gets harder when the scale is larger, but not everyone does this or needs to do this.

Can you tell us about your time as GM of Americas – what did you enjoy the most and what were the key drivers of your work?

For two years I was General Manager for the Americas and it was an all-round incredible experience. I was based in Miami and it was fantastic; super cosmopolitan - a melting pot of people, incredible weather and a vast amount of outdoors activities.

As GM, my role was much broader than Finance, or Product or Marketing; it covered growing our market, growing our relationships with major airlines, and growing our brand. I loved working in the US, there is a certain energy and optimism that I found really pronounced.

I also enjoyed being part of a smaller team for a while where I could understand and get closer to people in the team’s motivations, and spend more time developing the team. If anyone gets the opportunity to travel and work abroad for a year, I would highly recommend going for it.

What advice do you have for CAs who have recently moved to a North American role?

Deeply understand your business and the products. Use the CA network – you have this great network so reach out to them because they can be hugely supportive when you move countries.

What advice do you have for CAs in advancing to positions like CFO, GM or VP?

If someone wants to go for one of these roles, they need to have covered a huge amount of experience in an unnatural period of time to be able to speak with authority about these topics. Along with putting in the hours, you also have to be in an environment where you fail fast and learn quickly, or you see a significant volume of deals.

An important factor in the online space is an obsession with product. You can be great at your domain, but if you don’t understand the underlying product – how customers interact with the product and how to drive growth with that product – it’s hard to operate at C-level.

As a chief of a company, the underlying objective is to drive value and growth and to understand your domain expertise – bringing value is hard at that level if you’re not obsessed with the product.

I’ve seen senior finance people who report on the numbers but are unable to make a trade-off – if you asked where they would invest an extra $10m, they would tell you what their CFO or CMO would say, but they don’t understand their core product enough to answer the question.

They can report, but they don’t understand how to drive growth and can’t identify gaps in the market and areas that need funding. If you want to be at the C-level, you need to be able to answer that question from a business and a finance perspective.

Skyscanner was recently announced as the top flight comparison site by Which?; what has it been like having a hand in the growth of such a highly-regarded brand?

What’s really nice about Which? calling us out as a top-flight comparison is that we are an introvert company by nature that’s spent our life obsessing about how to make our product better for our users – when we make decisions, it’s user first, partner second and Skyscanner third.

As a CFO, we have to make difficult trade-offs that are right for the traveller. While our culture really is traveller first, we’re bad at shouting about it and getting that recognition, so this was important to us.

In terms of driving growth for such a highly regarded brand, we’ve a long way to go. For travel, people tend to shop around – we’ve got to own that space where we are the go-to place by starting with product. The role of growth is to amplify that and to make people more aware though different channels.

For those not in the know, what are Skyscanner Tribes and Squads and how do they support growth and success?

To go at speed, operating with departments and silos is very difficult, so we have a Tribes and Squad model similar to that first pioneered by Spotify. A Squad is a multidisciplinary team organized around a product or goal with metrics around that.

The team has people with different skillsets, like a marketer, analyst and product person, and ideally, they work together to solve a problem rather than problems bouncing from one team to another.

Working with the right mix of people around a problem is transformational for our business.

Squads work to a sprint cycle – they’ll fail fast, learn what worked and what didn’t, and then do another sprint. We have about 150 Squads that roll up into Tribes that roll up into the company.

Working with the right mix of people around a problem is transformational for our business. From a leadership point of view, it’s easier to manage without being overly prescriptive because as long as the goals are right and the Squad has the right people, you think about the 'what', the Squad thinks about the 'how', and together we look at the metrics of success.

You specialise in complex stakeholder management – what key skills do you think are required to manage relationships across VCs, shareholders, NXDs, etc.?

One of the most important things is to understand the lens through which people see the problem. A healthy Board should have a high-level alignment on whether to grow the company and the strategic direction to do this.

From there it’s important to pre-empt the different biases of the different members, and to manage these appropriately.

For example, a VC might have a three-year horizon and need to exit a fund – that will change their view of growth and the time horizon to exit, which might be completely different from other shareholders and NXDs.

You need to push to ensure aligned intent which means spending time to understand the lens people are looking through, which can be pretty difficult.

What CA skills are most valuable?

There are many beyond the financial nuts and bolts, from the legal courses and understanding contracts to data protection. At a top level, you don’t need to be a specialist in these ancillary areas, but you need enough knowledge to be able to second guess something.

The commercial accounting piece is essential in terms of running your business and in exploiting financial engineering through M&A.

Equally essential is your underlying understanding of basic performance metrics such as variable and fixed costs to drive operational gearing – using fixed costs to take pain now knowing your operational gearing will kick through later at scale, for example.

With CA training, you’ve got such an advantage to be able to naturally correlate things for performance and numbers from a P&L and balance sheet point of view.

Growing fast is about breaking things down to fundamentals and deeply understanding the financial implications of those fundamentals – cash is king at the end of the day, but you’re running a business, and all your key business metrics need to be right.

With CA training, you’ve got such an advantage to be able to naturally correlate things for performance and numbers from a P&L and balance sheet point of view – it’s hard for people who haven’t had that background to be involved in technical discussions.

It means you can really sweat your assets AND ensure you’re avoiding unacceptable risk at the same time.

What do you look for in the companies you consider for acquisition or partnership?

In our case, the innovation of the tech is very important, but we look predominantly at the strength of the underlying leadership team. Location is also important because each comes with a friction and an added cost because people can’t always foresee challenges in managing more offices.

We tend to look at product synergies to drive growth benefits (rather than cost benefits), and to do that, we also look at the people, the team and the culture.

About the author

Andrea Murad is a New York–based writer. Having worked on both Wall Street and Main Street, she now pursues her passion for words. She covers business and finance, and her work can be found on BBC Capital, Consumers Digest,,, Global Finance and


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