Staying Remarkable As Your Business Evolves

You may have heard HotelTonight’s recent news that we’ve expanded from a purely same-day model to helping people book last-minute rooms up to a week in advance. Some might call it a risky move for a company whose name is pretty closely tied to its offering (cue the HotelThisWeek jokes…)

I recently wrote about our War Room process, which is how HT comes up with its next-quarter priorities. We came out of our Q3 War Room with consensus that a single change would make the most impact on the business: expanding to allow bookings up to 7 days out. This would require us to rethink and rebuild our branding, UX, infrastructure, supplier engagement – basically every single aspect of the business, all in a single quarter.

Here’s why – and how – we decided to do it.

Reevaluate Your Product For Today’s Market

We founded HotelTonight back in 2010. Though we’re constantly reevaluating the product, and it has evolved and gotten better and better over the years, it was time to look at it with completely fresh eyes, in the context of today’s market.

We were thrilled with the way the business was growing, but were hearing over and over that while people loved the app, they would really love to be able to lock down plans a bit earlier. For times when you need to have certainty on your hotel accommodations – set up a breakfast meeting in the lobby, schedule a babysitter, or ship your luggage – booking a little ahead of time just made sense. We were also seeing that people were using their smartphones as their primary hotel booking device, and were looking for a more comprehensive offering from HT.

The signs that we should expand were all there. But...

Don’t Differentiate Just to Differentiate

We definitely had concerns about this move. We knew our product’s focus on same-day bookings made us unique, but with this expansion to a week ahead, would we stand out from the legacy travel companies? Would we still be remarkable? Would we need to change a lot more about the product to differentiate ourselves?

So we talked to our hotel partners, and brought in customers for focus groups. We looked at a ton of data. And we realized that our instincts were right – our existing differentiators (a mobile-only focus, great design, speed and simplicity, terrific deals at amazing hotels) would continue to set us apart – and now for more people, and more often. Differentiation for differentiation’s sake would be destructive to our simplicity. We did, of course, leave room for some new features, but only ones that are both simple and useful, like weather forecasts and themed “Playlists” with hotel recommendations for future travel.

Get Everyone On Board

Once we decided to how we would move forward, it was all hands on deck. Literally every single person in the company was on board, all-in, and worked with incredible intensity and focus to make this idea a reality in just one quarter. We called it Project High Line internally, after the NYC project that reinvented the urban park (and not coincidentally, the name of one of our partner hotels). We held weekly “High Line Friday” demos, shared frequent updates, ate cake and pizza together on some very late nights.

It was really important that everyone across all teams was engaged in the project and was fully in the loop about how things were coming along. The excitement and buzz in the office these last few months reminds me of the early days of HT. It’s been pretty amazing to see it in action.

Keep Your Name, Change Your Game

One important lesson we realized (after a lot of thought and research): we shouldn’t change our name. The name HotelTonight still embodies everything that led us to build the app in the first place. We realized that spontaneity and “last-minute” mean different things to different people, and that “Tonight” represents the endless opportunities that any night can bring. Just because our “booking window” changed doesn’t mean we’d changed who we are.

While making this move was definitely a risk, that’s what bold companies do, and it can certainly pay off. The response from both consumers and our hotel partners so far has been overwhelmingly positive – everybody wins. Companies with great teams can make big things happen, fast. In fact, we’re already hard at work building our next big thing (and no, it’s not HotelNextYear).

What's the biggest professional risk you’ve ever taken (or seen a company take)? Was it worth it?

Photo: HotelTonight