logo
episode-header-image
Jul 2017
21m 38s

Charlie Osmond on the Battle Against Boo...

HotelTechReport
About this episode

In this engaging podcast episode, we dive into the heart of hotel technology with Charlie, the dynamic founder of Triptease, a company that revolutionizes how hotels drive direct bookings and enhance guest experiences. Charlie shares his entrepreneurial journey, starting from his frustration with booking family holidays to identifying a massive opportunity within the online travel market. He underscores the importance of targeting big markets and the decade-long vision required for startup success.

The discussion also illuminates the unique and playful essence of the Triptease brand, emphasizing its role in making a technical product fun and engaging. Charlie recounts the rollercoaster of the initial 18 months, marked by extreme highs and lows, and the transformative pivot when faced with legal challenges from booking.com, turning potential threats into opportunities.

Furthermore, the conversation explores the strategic maneuvers of OTAs expanding into direct booking services, highlighting the implications for hoteliers and the broader market dynamics. Charlie discusses the critical importance of assembling a senior management team and the evolution of his leadership role, focusing on unique contributions as the company scales.

Highlighting company culture, Charlie emphasizes transparency and the educational journey of growing a fast-moving business, aiming to inspire employees towards entrepreneurship. The dialogue also covers strategies for identifying early adopters among hoteliers and the pivotal role of inside sales in scaling the business.

Charlie reflects on the invaluable lessons learned from ignoring conventional advice, underscoring the importance of following one's conviction in product development.

Up next
Jun 2024
Accor CTO's Hotel Tech Masterclass: Cyber Security, Sustainability and More
In this episode of Hotel Tech Insider, we dive deep into the future of hotels and the technology driving them forward. Our guest, Floor Bleeker, the CTO of Accor, one of the largest hotel companies globally, shares insights into how technology is revolutionizing every aspect of A ... Show More
32m 52s
Jun 2024
Place Value Hotels' Founder on Building a Data Driven Economy Hotel Brand
Martin Kemmer, the Managing Director of PlaceValue Hotels, showcases a unique approach to leveraging technology in the hospitality industry in a recent conversation on Hotel Tech Insider. With a background in IT and a passion for data-driven decision-making, Martin's journey from ... Show More
33m 16s
Jun 2024
Radisson's Director of Operations on The Science of Digital Transformation
We discuss the future of hotels and technology with Patrick Apostolo, the Director of Corporate Operations and Business Transformation for EMEA at Radisson Hotels. Patrick shares his journey in the hospitality industry, highlighting the importance of digital transformation in dri ... Show More
45m 50s
Recommended Episodes
Sep 2024
Cyber Security Trends and Tips
Join us on the latest episode of Aviation Tech Talks with host, Jim Boccarossa, as we soar into the world of aviation technology! In this episode, we dive deep into the crucial topic of cybersecurity with expert guest, Sagar Pandya, co-founder of Middle Ground Technologies. Disco ... Show More
31m 27s
Jul 2024
Shifts in Aviation Aftermarket Technology
Join us for an engaging conversation with David Bettenhausen, the founder and CEO of Aerotrax Technologies. David and Jim reconnect after meeting on a panel discussing digitization in the supply chain. David shares insights into his background, having launched Aerotrax from his V ... Show More
35m 46s
Jun 2024
Top AI trends and strategies to make the most of them
Text us your thoughts on this episodeTechnological advances, surging investments and the competition for talent are all working toward one thing: artificial intelligence (AI) is fundamentally changing how business gets done. In this episode, Joe Atkinson, Vice Chair - Chief Produ ... Show More
19m 11s
Jun 14
The Secret CISO: Navigating the Human and Technical Challenges in Cybersecurity
In this episode of 'Cybersecurity Today,' hosts John Pinard and Jim Love introduce their unique show, 'The Secret CISO,' which aims to dive deep into the lives and thoughts of CISOs and similar roles, beyond the usual interview-style format. The guest for this episode is Priya Mo ... Show More
51m 57s
May 1
Building Readiness for AI Agents in Healthcare Systems - with Raheel Retiwalla of Productive Edge
Today’s guest is Raheel Retiwalla, Chief Strategy Officer at Productive Edge — a digital transformation consultancy focused on healthcare. Productive Edge works with payers, providers, and health tech firms to leverage AI, data, and modern platforms to streamline operations, cut ... Show More
33m 22s
Jan 2025
Revolutionizing Restaurant Tech: Yaro's Journey with PickPad
Revolutionizing Restaurant Tech: Yaro's Journey with PickPad In this episode of the Restaurant Technology Guys podcast, Jeremy Julian interviews Yaro, a multiple-time founder in the realm of restaurant technology. Yaro shares his background, detailing his migration from Ukra ... Show More
31m 34s
Feb 2025
TCP090: Powering the New Wave of Hospitality with HTC VIVE
This episode features Dan O'Brien from HTC, who brings years of experience in tech innovation to the table. They discuss the importance of strategic business partnerships in the travel and hospitality industry, focusing on how these collaborations can lead to growth and enhanced ... Show More
40m 23s
Feb 2025
Managing End Point Storage in Hybrid Data Strategies for Financial Services - with Yonas Yohannes of Oracle
Today’s guest is Yonas Yohannes, CTO of FinTech and FIS at Oracle. An accomplished executive and author, Yonas joins us on today’s podcast to explain the evolving role of endpoint storage for driving new AI capabilities at the edge. He breaks down AI’s true value beyond the marke ... Show More
22m 21s
Apr 2025
Insights from a Tech Leader: Interview with TD Bank's Chief Architect Licenia Rojas
In this captivating interview, host Jim Love sits down with Licenia Rojas, Senior Vice President and Chief Architect at TD Bank. They discuss Licenia's journey in the technology sector, the importance of mentorship, and the role of continuous learning in career development. The c ... Show More
42m 56s
Jan 2025
Exploring the Past, Present, and Future of AI/ML
In this episode of the Data Science Salon Podcast, host Anna Anisin sits down with two influential leaders in AI and data science to discuss their experiences, challenges, and insights into the evolving landscape of the industry. First, Fatma Tarlaci, Chief Technology Officer at ... Show More
40m 47s