Headout
“Can a curated travel-experiences marketplace become the default global booking layer for tours, attractions, and live events at scale by optimizing discovery, conversion, and payment acceptance?”
Founded in 2015 as a same-day booking app for tours and activities in major cities, Headout initially competed in the crowded OTA/experiences space. During COVID-19, the company pivoted toward domestic travel and local demand, reaching EBITDA profitability in mid-2021 — a rare feat for a marketplace during the pandemic. Post-pandemic, Headout leaned into its global marketplace model, scaling to 10,000+ experiences across 150+ cities, embedding BNPL via Klarna and upgrading its payments infrastructure via Checkout.com to drive acceptance-rate improvements at global scale.