< Back to all articles


Download the Direct Booking Summit Chicago Key Learnings Report

Download your free report for insights, data & practical tips on everything from budgeting to pricing plus A.I. generated content & reputation management.

Sign up for weekly insights:


With over 40 expert speakers in attendance, the Direct Booking Summit Chicago was - as one happy attendee said - “by far the most practical, tangible, informative summit I have been to”.

Whether you were there in the room with us or not, you can still get the benefit of two days packed with real life industry learnings and strategies by downloading the Direct Booking Summit Key Learnings Report. Here’s a taste of what it contains…


Practical solutions to industry-wide problems

Blog image - Direct Booking Summit Chicago Key Learnings report - Dan Wacksman

Dan Wacksman, Co-Founder of hotelBschool.com and Founder/CEO of Sassato, set the perfect tone for the event with an opening presentation asking why hoteliers are still stuck trying to tackle the same age-old problems that they were grappling with ten years ago. His instructive presentation on how to break down barriers to problem solving provided some fresh thinking on how to overcome ongoing business problems.

We were also joined by Tim Peter, Founder and President of Tim Peter Associates, who calculated the true, monetary cost of outsourcing marketing and sales to OTAs. The total bill added up frighteningly fast, but Tim provided a three-step plan to take back control of your bookings and reclaim that lost revenue.


Tangible, time-saving A.I. strategies for hotels

Blog image - Direct Booking Summit Chicago Key Learnings report - Satvika

It’s the topic everyone is talking about but the Direct Booking Summit only offers practical, actionable content - so when we tackle A.I., it comes with step-by-step plans and usable frameworks to apply in a hotelier’s daily life.

Star speaker Alex Velazquez, Vice President of Digital Marketing at Westgate Resorts, stole the show with a presentation explaining exactly how hoteliers can achieve ‘SEO success in 30 minutes’ using various A.I. tools. Live on stage he walked through the exact process to follow to generate the right content to secure incredible SEO performance for your hotel. We’ll be sharing the full recording of this amazing session very soon, so make sure you’re signed up to the Triptease newsletter to be the first to know.

We were also joined by Satvika Ananthanarayan, Strategy Insights & Planning Manager, ZS Consulting, who shared a ‘Pragmatists Guide to using A.I. in Hospitality’. She provided a tried-and-tested framework that hoteliers can use to decide if a problem they’re facing could be solved using A.I. 2.0 tools.


Sharing successes and learning from mistakes

Blog image - Direct Booking Summit Chicago Key Learnings report - Chatbot session

One of the greatest things about the Direct Booking Summit is how open and honest our speakers and attendees are prepared to be. This year we had so many incredible sessions from hoteliers who’d had great successes, including:

  • How to have a ‘million-dollar month with Michelle Klein, Director of Ecommerce and Digital Marketing at Schulte Hospitality
  • A masterclass in reputation management from Adrienne Fors, Senior Manager of Marketing and Distribution at Kasa Living
  • Tips on how to audit your content to ensure your onsite experience matches your on-property experience with Jason Pirock, Corporate Director of Marketing at Springboard Hospitality
  • A real life case study on the right way to do chatbot selling with Corrina Terenstra, Sales and Marketing Director at The Reef Resorts
  • A fireside chat exploring Four Seasons’s incredible A/B testing successes, with David Sistilli, Global Product Owner, Four Seasons
  • Innovative ideas on how to drive direct bookings through community engagement with Dan Smart, Director of Sales and Marketing at Dream Inn Santa Cruz

Equally as important were the sessions where hoteliers opened up about initiatives they’d tried that hadn’t quite worked out as planned. Sandor J Winkler, Corp Director of Sales and Marketing at The Villa Group, kicked off day two with a detailed look into the data behind his theory that hoteliers are looking at parity wrong. He was mid-way through an experiment at his own hotel, but had not quite been able to prove his original hypothesis. Regardless he was still able to share some really insightful learnings that were incredibly useful for other hotels.

Blog image - Direct Booking Summit Chicago Key Learnings report - Sandor

Similarly, Lori Kiel, Chief Commercial Officer at The Kessler Collection, shared two commercial strategies her team had tested during two low occupancy months, along with all the learnings on how she’ll do it differently next year.


Debates, discussions, budget battles and bingo cards

Blog image - Direct Booking Summit Chicago Key Learnings report - Budget Battle

The Direct Booking Summit will never be one of those dry industry events where the audience sits passively while somebody talks at them from the stage. We’re all about interactivity and action!

To that end, we had some fascinating debates this year - from Ian Sloan, VP Global Strategic Partnerships at SHR Group, and Kim Howard, Director Digital Marketing and Strategy at Remington Hospitality, building their foolproof direct booking strategy live on stage, to an insightful panel on holistic revenue management, a discussion with Marcus Hotels and Resorts on how they built their Commercial Team, and finally Dan Wacksman and Leslie Lew, VP of Revenue and Technology at Practice Hospitality, debating the perfect hotelier tech stack for 2024.

And we don’t just bring innovation to the topics on stage - this year we shook up the agenda with some brand new session formats too. Derek Brewster, Regional Director of Revenue Management at Lotte New York Palace and Lotte Hotel Seattle, hosted a panel of industry experts for the Big Budget Battle - a ‘Who Wants to be a Millionaire’ style quiz show to build the perfect budget for the coming year.

Meanwhile, Triptease’s own Senior Product Designer, Chimmy Kalu, presented the seven UX tricks that hotels can steal from OTAs today. The audience were given a bingo card and invited to cross off any of the tricks they were already doing until they completed their card. The key learnings? Lots of hoteliers couldn’t complete the card! That means there’s LOTS more opportunity to improve hotel website UX in the future.

Blog image - Direct Booking Summit Chicago Key Learnings report - UX bingo


Valuable insights from carefully selected technology partners

Blog image - Direct Booking Summit Chicago Key Learnings report - The Guestbook

When it comes to event sponsors, the Direct Booking Summit team curates a selected list of innovative partners who not only provide industry-leading direct booking solutions, but who can also hold their own on the stage!

This year we welcomed Jessie Linevsky, Strategy and Innovation Manager at The Guestbook, who taught us all about how to sell to Generation Z, while Mykola Sheludko, CTO of Sabre, shared key learnings and successes in hospitality retailing. Jason Craparo, CEO of Hovr, talked about content in context, and finally, Aaron Serrato, VP of Sales at Selfbook, walked the audience through the things that e-commerce leaders are getting right.


New Triptease innovation: On-site Price Match and Email Activation

Blog image - Direct Booking Summit Chicago Key Learnings report - Email Activation panel

It wouldn’t be the Direct Booking Summit if the Triptease Product team hadn’t come armed with brand new industry data as well as our latest innovations to help hotels drive direct bookings.

On day one Jonathan Hickford, Product Manager for Guest Applications, and Andrew Williamson, Product Manager for Parity, looked back over a year of learnings from Triptease’s game-changing Price Match on Meta functionality. They also launched the next phase of development for the product. Hotels will soon be able to automatically adjust prices when they’re being undercut to the website too - watch this space!

On day two Triptease Co-Founder and Chief Product Officer, Alasdair Snow, hosted a panel including Triptease’s Chimmy Kalu alongside Triptease clients Don MacCorquodale, Director of Revenue Management at One King West, and Karen Wilken, Marketing and Public Relations Manager at Fountain Head. They discussed what hoteliers can learn from ecommerce email strategies as well as sharing how Triptease’s new Cart abandonment and ‘Back-in-stock’ emails have changed the game for their direct bookings.


What are you waiting for? Download the report today! 

Similar posts

Get the latest in hotel revenue, distribution, marketing and much more:
By registering, you confirm that you agree to the storing and processing of your personal data by Triptease as described in the Privacy Policy.