Headout completes second ESOP buyback for over 250 employees

Headout is now serving over 40 million guests across more than 100 cities

Headout has completed an Employee Stock Ownership Plan (ESOP) buyback, the New York-based startup that helps people book travel experiences worldwide said July 16, marking the second such transaction in three years.

More than 250 employees at its 11 global offices participated in the buyback, fully funded through the company's balance sheet, it said.

"This second buyback is a celebration of the people who’ve helped us build this one-of-a-kind global experiences brand. Our journey has always been powered by belief, and this is how we honour the people who believe in our mission and make it real every day," Headout co-founder Varun Khona said.

The buyback comes at a time when ESOP liquidity events are becoming more common among growth-stage companies as a way to attract and retain talent in an increasingly competitive job market.

The buyback follows a period of sustained growth, with Headout serving more than 40 million guests in more than 100 cities and driving over $3 billion in cumulative tourism impact, the company said.

Founded in 2015 by Khona, Suren Sultania and Vikram Jit Singh, Headout runs a managed marketplace that offers curated travel experiences including expert-led tours, cruises, adventure sports, water sports, events and local activities in 81 cities across the world.

The startup creates and curates its experiences, upgrades the technology and delivery infrastructure for the experience providers and standardises the end service to ensure consistent quality. It claims this approach helps the startup deliver a higher conversion rate than the existing aggregators.

Headout claims to have grown tenfold in recent years, expanding in North America, Europe, the Middle East and Asia. It is aiming to launch in over 500 cities within the next 18 months.

"Our ambitions are getting bolder. We want to 5x our scale in the next 18 months and to become an AI-first experiences company that will set the standard for what cutting-edge AI consumer applications look like. Given these lofty goals, it is critical that we live up to our operating principle of valuing our team," Khona said. Headout's first buyback was in 2022.

It has raised over $60 million funding from investors such as Nexus Venture Partners, Version One Ventures and Glade Brook Capital until now. In May 2024, it acquired Y Combinator-backed Dabble to boost its AI capabilities.

Headout said a new series of product launches, including ExperienceAI, Smart Pickups, Headout Theatre, Drops, Headout Now Pay Later and Smart Pricing, are driving its next phase of growth. It also plans to introduce AI agentic solutions to boost real-world experiences in September.