Jessica Gillingham

Jessica Gillingham Profile Photo

Founder & CEO

From her initial venture Triptoes, which was a 2015 Guardian Start-up of the Year, to an award-winning career in hospitality technology public relations and marketing, Jessica has become an established name in the lodging technology industry.

After the Applause: Real Takeaways from VRMA 2025 with Tim Rosolio, Ela Mezhiborsky, and Jessica Gillingham
Nov. 18, 2025

After the Applause: Real Takeaways from VRMA 2025 with Tim Rosolio, E…

Send us a message! VRMA International 2025 is in the books and if you were there, you probably felt it too: this year hit differently. More people, deeper conversations, and a sense that the vacation rental industry is enteri...

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The Role of PR in Building Your Vacation Rental Brand with Jessica Gillingham
Aug. 14, 2024

The Role of PR in Building Your Vacation Rental Brand with Jessica Gi…

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: http://get.hostaway.com/alexandannie In this episode, we dive deep into the world of public relation...

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