Headout
PrivateLast Round
Series B
Extension
Feb 2, 2022
Total Funding Raised
$53.8M
Momentum
Top 25%
of companies Caplight tracks
Company Overview
Headout is a travel technology company that provides an on-demand mobile marketplace for travelers to discover and book local experiences, tours, and activities at discounted prices.
Sector
Consumer & Commerce
Verticals
E-commerce, Mobile Commerce, NLP & Conversational AI
Business Model
B2C
Customer Profile
Marketplace Commission, Revenue Share
AI Layer
Application
Keywords
Historical Pricing
Historical view of private secondary pricing and transaction trends.
Headout Comparables
Compare Headout with similar companies based on industry and business-model similarity.
| Company | Similarity | Market Cap |
|---|---|---|
| Expedia Group | 88% | |
| GetYourGuide | 87% | |
| Thrillophilia | 83% |
Headout Funding Rounds
Historical fundraising activity
| Round | Date | Amount Raised | Valuation | Investors | Sources |
|---|---|---|---|---|---|
| Series B Extension | Feb 2, 2022 | ||||
| Series B | Sep 8, 2021 | ||||
| Series A | Jul 12, 2018 | ||||
| Seed | Apr 23, 2015 |
Key People
Founding team and executive leadership
Headout Investors
Notable investors and investment history
| Investor | Rounds |
|---|---|
| Arena Ventures | Seed |
| Dreamit Ventures | Seed |
| Haystack | Seed, Series B |
| 500 Global | Seed, Series B Extension, Series B |
| DI Investment Holding Limited | Seed |
| Ludlow Ventures | Seed, Series B |
| Practical Venture Capital | Series B |
Market signals
Structured signals derived from secondary market and firmographic data.
- Apr 13, 2026
Reached $130M in revenue.
- Apr 13, 2026
AI-powered tour guide product named Dex is in early stages.
Recent news
Latest coverage and updates
- launchesJul 28, 2026
Headout launched Clockwork on Jul 28th '26.
Headout Filings
Explore SEC and related filing metadata, where available.
| Type | Date | Amount Offered | Amount Sold | Filing | Pages | Download |
|---|
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