“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.
Headout processes payments through Checkout.com.
The Embedded Finance Index 2026 maps 2 layers in Headout's stack: Payments / PSP (Checkout.com); Lending (Klarna BNPL — installment payments for travel experience bookings).
Headout was founded by Varun Khona, Utkarsh Dwivedi and Suren Sultania and is founded in 2015, headquartered in New York, NY, USA (82 Nassau Street, #60351, NY 10038).
Headout has raised $43M+ in total (latest round: Series B extension, February 2022).
Get a read on where your own stack stands against Headout and the rest of its category — what they built versus bought, which providers they use, and where the gaps in your own strategy and competitive set actually are.