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

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

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

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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Coffee Chat: Triptease & HEBS Digital
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Coffee Chat: Triptease & HEBS Digital