Headout Buys AI Startup Dabble to Boost Travel Experiences Search

Headout, which runs an app to help travelers book experiences, said Friday it had acquired Dabble, a startup that helps companies use artificial intelligence (AI) more effectively.

Headout had already been using AI for content creation, fraud prevention, and price-setting. Its platform covers 125 cities worldwide and serves more than 27 million people. The company said it turned profitable in 2021 and that it raised more than $40 million in venture capital in 2022.

Dabble launched in 2021 and works with e-commerce sites like Amazon, Wayfair, Pottery Barn, and Etsy. It helps companies accelerate content creation, create better work pipelines, and build more accurate models for products. The company went through the Y Combinator startup program. 

Headout’s co-founder and CEO, Varun Khona, said he couldn’t publicize how his company will use Dabble’s expertise just yet.

“We will have something meaningful to share later in the year as a big launch,” he said.

For now, Khona shared three big themes: personalization, immersive media, and creating new experiences “with AI at the center of it all.”

AI’s streamlining potential

Industry experts see potential for AI to help small travel-experience businesses bolster their operations.

“Experiences is the most diverse, most fragmented travel sector,” said Douglas Quinby, co-founder and CEO of Arival, adding that the vast majority of operators are small or micro businesses that have varying levels of technology adoption.

The industry has particularly high expectations of AI to help with discovery and recommendations, according to Quinby. “Travelers can be overwhelmed with choice. Viator alone offers more than 4,000 tours in Rome,” he said. “The hope is that smart AI tools could offer a better recommendation engine.”

Craig Everett, CEO of Holibob, which provides booking technology to online sellers of travel and tourism boards, said that AI can help customers navigate this fragmented and overwhelming landscape of options.

He added that Headout is focusing on providing customers with quality over quantity. “Rather than overwhelm customers with choice, they’ve smartly pre-curated what travelers see,” Everett said. “The next step, and something we’re working hard on, is building the relevancy on top of that product quality to even further help travelers narrow in on the perfect things for their trip.”