Summary
Highlights
Ian Fishwicker and Chris Godsmark introduce Shane Corstorphine, former CFO of Skyscanner, as a serial entrepreneur instrumental in scaling Skyscanner from a small startup to a global company with a valuation exceeding £1 billion. Shane joined Skyscanner when it had 50-60 employees and was already profitable, having secured early investment from Scottish Equity Partners.
Shane explains his role in the leadership team alongside Gareth, the visionary CEO, and Mark Logan, the COO. Shane, with his background in tech and banking, focused on execution, numbers, and integrating strategy with people. The team's dynamic involved continuous whiteboarding sessions to translate Gareth's complex vision into actionable and understandable strategies for a rapidly growing workforce.
Skyscanner initially relied on free channels like SEO to drive traffic. Shane discusses the 'frequency problem' in travel, where customers return infrequently, making it challenging for product-market fit. He highlights their strategy of testing many markets with lightweight approaches, tracking key metrics (acquisition, activation, retention, referral, revenue), and then scaling with paid channels and brand awareness once product-market fit was achieved.
Shane emphasises the significance of deep equity among employees (16% of equity was available to staff) for fostering culture and openness. He shares the strategy of proactively managing investor relations through regular updates, even when not actively fundraising. He also recounts a key decision to conduct a share buyback for employees before the Sequoia investment, ensuring employees understood the value of their equity and providing liquidity.
The discussion delves into how Skyscanner attracted investment from Sequoia, a preeminent Silicon Valley venture capital firm. Shane explains that a key factor was positioning Skyscanner as a 'power curve' in the travel industry, similar to how Sequoia had invested in Kayak. The investment boosted recruitment, provided access to valuable insights from other successful tech companies (like LinkedIn and Square), and brought a 'just do it' mentality to the board, balancing the cautious British approach.
Skyscanner adopted a unique multimarket scaling strategy, entering numerous markets simultaneously with a 'light touch' approach. Instead of focusing on one large market like the US, they prioritised Asia, opening their second office in Singapore. This 'test and learn' philosophy involved quickly identifying markets with product-market fit and rapidly scaling them, while discontinuing efforts in unprofitable regions, such as Thailand where banking penetration was low.
Shane details a significant fundraising round of £200 million at a £1 billion valuation, which was the largest private tech raise in the UK at that time, bringing in five new international investors. He then moved to Miami to lead the Americas, and the company was ultimately sold for $1.75 billion in 2016. He attributes the success to the solid foundation laid by the team and the strategic decisions made during his tenure.
After the sale, Shane took time off, reflecting on his experiences, and now, he advises on four boards and coaches eight scale-up founders, contributing to the Scottish economy. He continues to be 'obsessed' with creating more billion-pound businesses, demonstrating his passion for scaling companies and people.
Ian and Chris reflect on the interview, highlighting the unique combination of a technologist and finance expert in Shane. They underscore the importance of the three-person leadership team (visionary, scaler, executioner) and Skyscanner's counterintuitive approach to international expansion—entering multiple markets simultaneously and being ruthless about pulling out of those without strong product-market fit. They also discuss the 'frequency' concept and the profound impact of global market conditions and timing on the company's trajectory.