For most people booking a hotel, their initial instinct is to go to an aggregator: from TripAdvisor to Trivago, Expedia to Booking.com, it’s a competitive market. But are you getting the best deal? Commissions are high and, even (as is the case in Europe) where hotels and third parties contract that they will charge the same rates, the aggregators can manipulate the position of search results. It’s a murky world, and Triptease wants to put things right. The hotel business is fragmented, with independents up against the major chains and Triptease levels the playing field by giving hospitality businesses a platform to increase direct bookings. It creates a smoother customer experience and transparency for everyone – including telling customers “this is what you would pay elsewhere”.

Founder and CEO, Charlie Osmond says that the goal was always to improve the booking experience – after all, why should we always end up with thirty open tabs? Yet Osmond’s first product was “a sort of Instagram meets TripAdvisor”, a socialised version of reviews where pictures of customers’ experiences could be processed with photo filters for a sharable review. It was weak. Two pivots followed “and it was pretty bleak for a long time. We’d raised money and then stopped doing what we’d said we were going to do. We had one last roll of the dice and suddenly everything changed. We went from having thirty hotels to three hundred in a few months.”

US customers push a business forward…

With a credible take-up in the market, expansion to the US was inevitable and rapid. Triptease co-founder, Alexandra Zubko, was based in New York and handling business there already. The leading hotel chains (Marriott/Starwood, Hilton, ICG) were predominantly based in the US – as were the majority of mid-sized chains. And with the company’s rate of expansion, another round of funding was going to be required; and Charlie felt that he could raise on better terms in the US.

“I also felt that they were most open to adopting new technology”, says Charlie, “They would push our thinking, and that would help us evolve our category.”

In late 2015, just six months into “the business that could work”, Charlie Osmond uprooted to the US.

…But US systems can hold you back

He is sanguine about the complexity of setting up in the US.

“I realise now how fabulous the company creation process is in the UK. I don’t think enough people realise how good we’ve got it and how easy it is to set up a business in the UK, compared to anywhere else in the world. There is far more paperwork and friction here.” Equally, though, he says: “Having said that, thousands of companies do it every year. Yes, there were new laws that we needed to understand, but you just get on and do it. There are plenty of people to help you - a lot of lawyers and advisors who will happily take your money!”

“It wasn’t about me!” – successfully splitting leadership duties

Today, the business employs around 100 people, 70 in London and 30 in the US. But Charlie says the biggest surprise was that the centre of gravity of the business did not follow him.

“Because I had my finger in everything, I assumed that when I got to the US, the headquarters and the weight of the business would shift with me. But it didn’t! It didn’t matter where I was: it wasn’t about me.” Most entrepreneurs would count this as an exceptional success – and it’s partly down to Charlie’s brother, James.

“Alexandra refused to let me leave the UK until I’d found someone else to run that operation. Alastair (CPO), the other co-founder, had his hands full running the product. It just so happened that my brother had just sold a business and was looking for his next step. Now, I’d sworn time and time again that I would never work with my elder brother, but moving to another continent, the one thing I was looking for was trust, and obviously, I knew him better than anyone else!

“You don’t want to be hiring someone for nepotism, you want to hire them because they’re the right person; so I made him go through the interview process and I think everyone quickly realised that actually, we wouldn’t be able to find someone of his calibre, if he hadn’t been my brother!”

Solving the sales conundrum

The US team is, of course, sales focused, partly because it’s the obvious priority, and partly because, in Charlie’s words:

“The idea of hiring developers in the US totally put me off. It’s harder and it’s more expensive”.

There’s no substitute for local sales. “In many ways it’s a truism and wonderful thing, that when I open my mouth in front of an American audience, they for some reason give me a ten-point IQ benefit of the doubt”, says Charlie. “They assume you’re smarter. I’ve definitely felt that”. But scaled-up sales demands more. Selling to both very large and very small businesses, the US operation includes a sales team, a strategic accounts team for the major players and a customer success team to manage standards, ensure value alignment and feed customer insight back into the product. “Because we had quite a bit of confidence about the market, we very quickly hired a senior management team.

“But one of the big issues for us was: do we hire a global Head of Sales who commutes between London and New York, or do we hire a head of sales in each? We had to make that decision for both the sales organization and the customer success team. For the sales organization, we got lucky and we hired a fabulous VP, Sales with experience of the global role (along with bringing a Head of Sales over from the UK). For the customer success team, we handled it differently, we’ve got different leads for Europe and the US. But there’s no right answer: two people in two different parts of the world building processes for the first time can be problematic; equally we might not have been able to find an individual leader capable of moving the customer success function forward. You work with what you can get.”

That said, investment in leaders reduces the pressure on mid-level hires – including the notoriously expensive sales talent.

“Hiring sales people anywhere in the world is hard. Hiring salespeople in America if you’re British is on another level; because they all sound like they’re the best salespeople in the world in their last job."

"Because we had an experienced sales person from London coming over to the US who could manage a team and because the product is straightforward, we were able to hire straight graduates. Many are still with us. I wouldn’t have had the confidence to do that if we hadn’t had a Sales Manager who knew what he was doing.”

The value of an experienced transfer from the UK and the cultural value they bring is a sentiment expressed by many founders making the leap across the Atlantic. “We had a system in the UK and we were able to replicate it and hire people for whom it was their first role and get things done our way. Every time I see people from the company cross the Atlantic, it kills me – I think, ‘this is costing us a fortune in travel’- yet it has such value. It really is driving a much stronger connection across the business. We do an annual Christmas party and we actually fly the entire US team to meet the British team, so we bring everyone together globally. Again it’s expensive, but I think it’s really worth it.”

Triptease today has hundreds of US clients, as expected. But it didn’t attract US money.

The business achieved a $9m Series B from BGF Ventures, Notion Capital and Episode 1 – all based in London. Charlie is philosophical. “It wasn’t a waste of time, because there is always a benefit in understanding other points of view and I always learn from every time I pitch the business. But the bar on American VCs investing in British businesses is surprisingly high. Even though I moved out here, ultimately they could see that this company was really being run from the UK. One of them said to me, ‘I really like you, I love the business; we would definitely invest in you if the whole business was based in the US. But I can’t be bothered to get on a plane six times a year to fly to London’. I think you would have to have significantly more of the business here to get a US VC involved.”

Key takeaways:

• US customers help refine and improve your proposition.
• Make sure you have a capable and credible leader in your home base when you migrate.
• Sometimes it makes sense to matrix roles, sometimes you need a single leader.
• Get things done ‘your way’: export best practice from home rather than rewriting the rulebook for a new territory.
• Lastly, an English accent can work wonders!