LEADING the legal team that helped her employer – travel price-comparison website Skyscanner - secure a £1.4 billion takeover by Chinese travel agency Ctrip at the end of last year was, said Carolyn Jameson, career defining.

Not only did Skyscanner’s ownership model mean the work required to get the deal away was both legally complex and intellectually challenging, but the fact that so many smaller players in the Scottish tech scene have since vowed to become “the next Skyscanner” has been inspiring.

“It was such an exciting deal to work on and really exciting to see the reaction afterwards,” said Ms Jameson, who has led the business’s legal team since joining from Wolfson Microelectronics in 2013.

“It was a very dynamic deal. It was very complex because we had lots of different shareholder types and issues were coming in all the time.”

Luckily Ms Jameson and her eight-strong team had form when it came to M&A transactions. Though smaller in terms of value and market impact, Skyscanner acquired Barcelona-based hotel search company Fogg in 2013, mobile app developer Distinction and Chinese travel search firm Youbibi in 2014, and formed a joint venture with Yahoo! Japan in 2015.

This meant that with the exception of some drafting work, which was handled by Pinsent Masons, and matters relating to Ctrip’s listing in America, which US firm Fried Frank Harris Shriver & Jacobson dealt with, much of the work on the Ctrip deal was done in-house.

“I try to keep the majority of work in-house - the only times we really go to external firms is if we want something validated, if we have capacity issues or the work is in a jurisdiction that we’re not qualified in,” Ms Jameson said.

“A lot of the interesting work is now in-house. Long gone are the days when the in-house team did the admin and everything interesting went out [to law firms].

“People see something like this and they realise quite how interesting it can be.”

This is important to Ms Jameson, who noted that “in-house is very much a career path in its own right” that requires a different kind of skillset to that of a private practice lawyer.

“You have to be really interested in the business aspects, not just the law,” Ms Jameson explained.

For a business like Skyscanner that means showing an entrepreneurial flair as well as a deep understanding of everything from M&A and intellectual property to contracts and competition law. This is something Ms Jameson recognised right from the start of her career, when she landed a job at software company Novell despite having no experience of the sector or as an in-house lawyer.

“I always wanted to be a barrister [advocate] and after university I went to the Inns of Court School of Law [now City Law School, in London], but once I was there I didn’t feel it was for me,” Ms Jameson recalled.

“I came across the idea of going in-house, which at that point wasn’t really common - there weren’t so many in-house roles then.

“I applied for a role and went for the interview, but I didn’t get the job because they wanted experience and I didn’t have that then.

“I sent a letter afterwards thanking them and saying if they changed their mind I was here. The person they gave the job to dropped out and they got back in touch and said ‘you’ve got none of the experience but we like your attitude so come for another interview’.

“That’s how I fell into tech.”

When her boss in the Novell legal department told her he had felt held back by a lack of commercial experience, Ms Jameson decided to spend a year working in sales at the company, gaining the kind of commercial experience she believes is essential if an in-house legal function is to be fully integrated with the business.

“When I joined Skyscanner it had about 250 employees [it now has over 800] and very much still felt like a start-up,” she said.

“It struck me as a really great opportunity to build a team as I would like to see it and I tried to build it with a very commercial approach.”

This is particularly important in an online business like Skyscanner, where probes by bodies such as the Competition and Markets Authority (CMA) in the UK and Department of Transportation (DoT) in the US have created work for the legal department but are completely tied up in how the business as a whole operates.

In 2014, for example, the business successfully overturned a ruling relating to hotel discounts that came from CMA predecessor the Office of Fair Trading. Skyscanner, which was set up to allow consumers to trawl the internet for the best possible travel deals, felt the decision had not been in consumers’ best interests.

“The CMA looking at price comparison websites and the DoT looking at how airfares are distributed are integral to our legal team and to the business,” Ms Jameson said. “There’s a really common thread in the issues that we see.”

This, said Ms Jameson, is what ultimately makes the job so interesting.

“It’s an exciting area to be in because it’s very much developing,” she added.