January 23, 2019

Coffee Chat: Triptease & HEBS Digital

HEBS Digital’s Brand Marketing Manager, Garrick Lee, recently chatted with the Founder and CEO of Triptease, Charlie Osmond, to discuss his career, the beginning of his company, and some of his favorite products that Triptease has recently developed.


How did you end up in the world of hospitality, and what inspired the idea for Triptease?

Charlie: The very first incarnation of Triptease was an attempt to use social media to help people find the right hotel and then directly book it. I noticed that people love sharing travel photos on Facebook (with little impact/benefit on hotels) but they never shared their reviews from TripAdvisor (which clearly impact booking decisions). So, we created an app that felt like a mix between Instagram and TripAdvisor. Apple promoted us in their stores and put us at #1 in the travel category. And hotels promoted us to guests, as we always included free ‘book direct’ links to their websites. The user growth was blistering and the engagement was excellent.

However, we soon realized we were playing at the dreaming end of the travel planning journey, where booking attribution is tricky. So, tossing aside two years of investment and effort, we switched to creating conversion tools that live within a hotel’s current website and booking engine. The first of these was the antithesis of our app: Price Check was a widget designed to appear on the final page of a booking journey and show a price comparison to reassure the guest before they booked. The idea for that came from thinking, “What can we do to add value as close to the moment of conversion as possible?”

After the pain of spending all my savings and being forced to sell my house to keep going, launching with Price Check was nerve-wracking. Thankfully the results were great and we grew incredibly fast from launch.


What is your day-to-day like? What are some highs and lows?

Charlie: Four years on, the highs and lows have mellowed. Strong client growth, good funding, and an experienced team have provided us with a stable platform. I spend most of my time looking for opportunities to remove obstacles that are getting in people’s way, chatting with customers about new product requirements, and challenging everyone to improve quality and speed without loss of enthusiasm!


If you had to give one piece of advice to anyone who wants to launch a tech startup, what would you tell them?

Charlie: Assume whatever idea you start a business with will be the wrong one. And that’s a good thing. It removes the pressure of waiting for the right idea. There is no right idea, there is only a starting hypothesis and time in the trenches. Triptease is my third successful business and none of them have the same proposition today with which they began.


What do you do outside of work?

Charlie: Hotels are global and that’s great for collecting air miles, but a challenge for balancing family life. Outside of work I do my best to hang out with my kids. At the moment, if we’re not out and about, that mostly means playing chess or going into battle together on Fortnite.

My selfish activity is running. When we opened an office in America, I felt strangely compelled to run the New York City Marathon and was instantly hooked. I’ve now completed five, placing second in two of them. I’m a much better human on the days I run into the office, and it gives me a chance to listen to great audiobooks.


How can Triptease help hoteliers, and what is your personal favorite Triptease product?

Charlie: We track the behavior of guests across thousands of hotel websites. We collect billions of micro-signals and use them as triggers to deliver personalized messages to guests when they visit a hotel website. This increases conversion rates by 10-30%.

I know the strategy at HEBS Digital and NextGuest Technologies is to join hotel marketing activities with CRM and an updated website for a bigger overall impact. A similar ambition is at the heart of my favorite Triptease product. We recently launched AI-driven meta-bidding. The exciting differentiator has been conjoining live parity data with guest behavior data from the website to drive smarter bidding decisions on meta.

Most guests start on Google. Meta is an increasingly prominent part of Google’s real estate and now hotels can wield data and dynamic bidding like the very best OTAs.



Triptease makes hotel data work harder to increase revenue direct. The Triptease Platform integrates with a hotel’s website and booking engine, identifying the most valuable guests then working across the entire customer journey – from acquisition to conversion – to make sure they book direct. With coaching, content and community provided by the Triptease team, hoteliers can take back control of their distribution and become experts at driving direct – intelligently.

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About NextGuest Digital:

NextGuest Digital uses the latest in digital marketing technology to assist hotel brands in crafting their digital presence. Through the agency’s smartCMS®, Content Personalization Engine, Smart Data Marketing, and other innovative initiatives, hoteliers see a drastic boost in direct bookings, as well as lower distribution costs and an increase the lifetime value of guests. NextGuest Digital is part of NextGuest, an all-encompassing partner that helps hoteliers acquire, engage, and retain their next guest. Based in New York City, the company is comprised of NextGuest Digital, CRM, Labs, and Consulting.

www.nextguestdigital.com | (800) 649-5076 | hello@nextguest.com





Editorial Contact:

Garrick Lee
Brand Marketing Manager
Phone: (212) 752-9425
Email: garrick@nextguest.com