Headout

Headout

Platform for booking local travel experiences

Overview

Headout connects travelers with local experiences and attractions through an online platform. It partners with local tour operators, attractions, and experience providers to offer a wide catalog of activities, including theme parks, city tours, cultural experiences, and adventure activities, which it aggregates for easy discovery and booking. The platform uses a commission-based model, earning revenue when a customer books an experience. It enhances user experience with real-time availability, instant booking confirmations, and live chat support with local experts. What sets Headout apart is its scale and focus on seamless, instant bookings and direct access to local experts, backed by a broad, globally distributed catalog of more than 10,000 experiences used by millions of guests. The company aims to simplify and elevate city experiences by becoming the trusted, convenient source for booking local activities around the world.

About Headout

Simplify's Rating
Why Headout is rated
B-
Rated B on Competitive Edge
Rated B on Growth Potential
Rated C on Differentiation

Industries

Consumer Software

Company Size

501-1,000

Company Stage

Series B

Total Funding

$66.1M

Headquarters

New York City, New York

Founded

2015

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Simplify's Take

What believers are saying

  • Headout joined eu travel tech on May 24, 2026, strengthening European industry access.
  • Partnerships with QPAC, Stage Entertainment Spain, and Mandai expand high-intent inventory in 2026.
  • ESOP buybacks in 2026 signal retention strength, supporting execution through continued global hiring.

What critics are saying

  • Booking reliability still depends on partner APIs; one throttled account can break multiple tours.
  • Headout's marketplace moat weakens if Viator, Tiqets, or direct operators match its integrations.
  • If inventory freshness or partner access degrades, checkout failures erode trust and kill repeat bookings.

What makes Headout unique

  • Headout's June 2025 Dabble acquisition adds AI, computer vision, and spatial computing capabilities.
  • Its direct API integrations with Cirque du Soleil and Delfont Mackintosh deepen supply exclusivity.
  • Clockwork inventory optimization launched in 2026, cutting ghost-slot failures from 10.6% to 4.7%.

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Funding

Total Funding

$66.1M

Below

Industry Average

Funded Over

6 Rounds

Series B funding is typically for startups that have proven their business model and need more funding to expand rapidly—often by entering new markets or adding more products. Investors are usually venture capital firms that specialize in later-stage investments.
Series B Funding Comparison
Below Average

Industry standards

$35M
$30M
Headout
$45M
Linktree
$65M
Substack
$100M
ClickUp

Benefits

Unlimited sick leaves including period leaves for women (and transgender people).

Unlimited mental wellness leaves.

No ceiling general leave.

Gender neutral 26 weeks leave for primary caregiver and 30 days for secondary caregiver. Applies for non-natural birth including adoption, surrogacy and same-sex partners.

1. In India, we provide a health insurance **cover for INR 7 lacs** for yourself, your spouse, your children and your parents (up to 6 in total). For other countries, we follow **local best practices**. Details be will be added here shortly.

50% off fitness class memberships.

Medical tele-consultation with doctors [India only].

Wellness programs once a month.

Online health platform(s) subscriptions.

Employee Assistance Program. We've got your back.

1. $500 Headout credits to, you guessed it, head out to any of our experiences around the world.

Paid courses and sessions for your learning & growth.

Access to conferences and meetups.

Community Lunches twice a week across all offices.

Travel across our global offices if your role demands it.

If your role requires you to move countries, we will do whatever it takes to take care of you. We are not limited by any policies when it comes to getting great talent to join us.

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

0%

2 year growth

0%
Headout
Jul 28th, 2026
The system behind a slot that stays available | Headout Hackin'

The system behind a slot that stays available | Headout Hackin' A booking can look available right until it fails at checkout. Clockwork checks inventory exactly when it matters, reducing ghost slots, protecting partner APIs and making the path from discovery to booking far more reliable. | July 28, 2026 Headout Inc noticed a simple problem guests were facing: the time slot they had chosen could disappear just as they were about to book. Hundreds of guests encounter this on Headout every day, not always because demand suddenly spiked, but because the availability Headout Inc showed them was already out of date. Somewhere between its last check with the supply partner and the moment the guest tried to pay, someone else had taken the slot. Internally, Headout Inc call this a Live Inventory Check failure. To the guest, it simply feels like a broken promise. So Headout Inc decided to fix it during Hackin' and called it Clockwork. Why fresher inventory is not a simple fix. Headout connects guests to experiences through dozens of supply partner systems, each with its own APIs and restrictions on how often Headout Inc can ask what is still available. The obvious solution is to refresh inventory more frequently, but every partner limits the number of API calls Headout Inc can make, and exceeding that allowance can throttle every experience connected through the account. Headout Inc had a fixed budget of calls and needed to spend it where it would have the greatest impact. The idea of an intelligent sync optimizer had surfaced before, but the problem could still be managed manually, with someone increasing the frequency of one tour and reducing another when failures became visible. That approach worked just well enough to delay a better one. When Hackin' at Headout began, the ability to configure every tour independently had just shipped, giving Headout Inc the foundation to build the system properly: fully automated, with no manual knobs. The scoring problem became a systems problem. From the outside, Clockwork looked like a ranking exercise: score every tour by how urgently it needed fresh inventory, then assign a sync frequency. The first brainstorming session revealed the iceberg underneath. Booking velocity mattered, but a fast-selling tour with a high failure rate required a different response from one selling just as quickly with almost no failures. The model had to balance several signals, ignore small fluctuations so it did not react to noise, and treat frequency changes proportionally, so moving from 15 to 30 minutes felt equivalent to moving from six to 12 hours. It also had to respect rate limits across tours sharing the same partner account, distribute the budget fairly when demand exceeded supply, detect zero-inventory segments wasting calls, pause broken tours automatically and spread schedules out so refresh jobs did not fire together. Every feature had to coexist without producing contradictory behaviour, and one aggressive configuration could overwhelm a partner API and throttle the entire account. Clockwork had stopped being a weekend scoring model and become a genuine systems design challenge. Proving that fresher data changed outcomes. Before building the complete system, Headout Inc tested the eight tours with the highest Live Inventory Check failure rates and increased their sync frequency to once every 15 minutes. The aggregate failure rate fell from 10.6% to 4.7%, more than halving the problem and confirming that stale inventory was a root cause Headout Inc could directly influence. Headout Inc then extended inventory windows for tours from a major theme park partner, fetching availability further into the future than before. That generated hundreds of incremental bookings from guests planning months ahead, bookings that could not have happened earlier because the inventory had never been available to see. Three people, one production system. Madhav and Himanshu built the scoring engine, rate-limit distributor, pipeline and dashboard, while Shriyan brought the product context needed to ensure the team was building something complete enough for production, not merely clever enough for a demo. In less than two days, the team worked through the partner constraints and failure modes that had kept the idea on the backlog and turned it into a functioning system. What is live now. Clockwork is now in production through a phased rollout across Headout's supply partner network. It scores tours, adjusts sync frequencies, respects partner-level rate limits, pauses broken tours, reduces calls to zero-inventory segments and diffuses schedules so jobs do not spike simultaneously, all without manual intervention. The next step is to extend inventory windows across more partners, turning the theme park experiment into a platform-wide capability. Hackin' at Headout is its internal hackathon, where small teams have less than two days to turn real problems into working products. Interested in building with Headout Inc? Explore open roles at Headout.

Headout
Feb 24th, 2026
Headout earns Great Place to Work(R) Certification across India, Germany, and the UK.

Headout earns Great Place to Work(R) Certification across India, Germany, and the UK. Inside headout February 24, 2026 Headout, the global marketplace for real-life experiences, has been certified as a Great Place to Work(R) for the second consecutive year. This year's recognition expands beyond India to include teams in Germany and the United Kingdom for the first time, marking an important milestone as the company continues to grow its global footprint. The Great Place to Work(R) Certification is based entirely on employee feedback and is an independent assessment of workplace culture. For Headout, the expanded recognition reflects the company's continued effort to build a high-ownership environment as its teams scale across markets and geographies. "At Headout, our ambition has always been to build a company where people can do their life's best work," said Varun Khona, CEO and Co-founder of Headout. "Being recognized again as a Great Place to Work, and now across multiple countries, is an encouraging signal that we're moving in the right direction as we continue to grow." As Headout enters its second decade, the company is focused on building a culture that can scale alongside the business - one that encourages ownership, collaboration across borders, and a strong sense of responsibility toward the problems teams are solving. "This recognition matters because it comes directly from our teams," said Manisha Naik, Head of Culture & Talent at Headout. "Culture is something you build deliberately as a company grows. Our goal is to create an environment where people can take ownership, challenge ideas, and build meaningful things together." As Headout continues to expand its global team and operations, the company remains focused on strengthening the culture that has helped power its growth so far, and ensuring it evolves alongside the business in the years ahead. About headout. Headout is home to the world's best real-life experiences, from tours and landmarks to live shows and local activities. By building experiences that matter, it makes heading out easier, faster, and more delightful. Through its managed marketplace, the company curates top experiences, builds technology and delivery infrastructure for providers, and ensures consistent quality for guests worldwide. Since launch, it has welcomed 48M+ guests from 196 countries across 400+ cities, generating $3B+ in local economic impact. Backed by $60M+ from top-tier investors, Headout is headquartered in New York with 11 global offices.

Leisure Media Limited
May 8th, 2025
Ticketmaster announces multi-year partnership extension with Crown Resorts

In an Australian first with Ticketmaster, Crown will also partner with Headout, a leading online travel marketplace, to enhance its event reach.

VidhiGrha Tech Private Limited
Mar 17th, 2025
Headout has partnered with House of Creators(TM)

Headout has partnered with House of Creators(TM) to harness the power of influencer marketing!

Headout
Oct 1st, 2024
Ready, set, Drop: Headout drops prices to $10 on select experiences in Dubai and London

Headout is thrilled to announce the launch of 'Drops,' a brand-new feature that brings the most incredible experiences to travelers at unbeatable prices.

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