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Going Global: Charlie Osmond of Triptease

In this new series, we’re interviewing leaders from companies of all sizes, who all face the same challenge: how do you tackle global growth?

Today we caught up with Charlie Osmond, Founder of Triptease, an online platform helping hotels engage with customers and significantly increase direct bookings.

What are the challenges of opening in new countries that people don’t expect?

You should assume the first people you hire are the wrong people. Always work on the basis you are more likely to get it wrong than right.

It can be very easy to get the wrong sense of people’s network in the market, capability and more. It can also be hard to give people the appropriate support in those early days.

It’s also relatively easy to kid yourself about the amount of time you need to invest in helping them. In your own office, you might allocate 2x weeks onboarding and training then let them be independent. But at a distance, the two weeks you count locally doesn’t include all the watercooler conversations, or turning to you to ask a question.

If they’re in your office and something is 10% wrong, sitting together you will fix those things — at a distance, this can be much harder.

What helped you attract your first international customers?

In the most part, they discover us online — through content, which gets shared and reaches new people. We also attend a lot of conferences, where an agenda in Berlin might get the interest of someone from Eastern Europe.

PR is also another route to getting your story told, it might be written by an English journalist on English website but it can get read around the world.

How do you decide which country to expand into next?

It’s just a simple matter of looking at market sizes and considering how customers are distributed or contactable. Think about likely adoption between countries and what competitive challenges you may face.

What regions did Triptease move into first and why?

We opened in London, then setup in New York as the next step. The strategy there was that we knew the US market was enormous and we needed to access it. You can’t deal with America in general from a UK timezone.

By contrast we didn’t immediately feel need to open in Europe, because can speak to customers there or fly out when needed easily. For Singapore, where we recently opened, it was about timezones and tackling cultural differences.

What were the most effective strategies you pursued to scale sooner or faster?

It’s all about the amount of time senior management spend in the new region. New York was fastest because two co-founders were out there. In Asia, we have senior management but I think if one of us could move out there for 6x months, I’m sure it could help it go faster.

This is partly because they will push things to happen in the market, but also because they are more capable of influencing head office. That’s a crucial skill.

How do you get good at it?

Trial and error really.

One aspect for us: my brother James, the COO, had led his previous company into the US and other countries — and made plenty of mistakes that now help us. There are loads of events that advise on this, and you pick up bits and pieces, but there’s nothing like real experience from a team that has already done it.

Has where you came from helped you make that journey?

I’ve lived in London for my whole life, and I feel privileged to be surrounded by people from so many different cultures. I hope that has given me a more international mindset. That helped us think international from the first step.

There are also many people from the UK that have done international expansion before, because they were part of UK headquartered international businesses.

What’s the balance of the challenge between geography and language?

Another challenge I’d add is different market maturity. Asia is ahead on the US on mobile, so they are ready for certain products faster. But they are behind on consumer travel tech spend. We’re spinning plates here, and if one slows down you end up focusing on it more. So it’s a relatively even balance. The timezone is a real pain but you just live with it, can’t do anything about it.

Cultural difference have meant we’ve targeted Singapore instead of, say, Kyoto. It’s a closer cultural link to Osaka, or something. Equally other companies might start in Sydney, if coming from Europe.

What advice would you give yourself if you could go back?

Go and live there for 6 months. I have a family and kids, which is a real challenge — but that’s without question the single thing you can do to have more impact than else.

Anything else you’d like to add?

I think for satellite offices, ultimately they will always feel like a satellite. They’re at distance from decision-making. That’s why we put a lot of time and effort into driving that connection. For example, we use Slack a lot, which is a great way to feel the business is alive 24 hours a day. You wake up to comments from Singapore and they wake up with comments from New York.

We also try and make company nights out in London, NY, Singapore on the same night. Then for Christmas, we fly everyone in from everywhere. It’s expensive but we think it’s worth investing in.

You have to really try to make people feel more connected.