Headout

Headout

Connects travelers with local experiences and attractions

About Headout

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

Industries

Consumer Software

Consumer Goods

Company Size

501-1,000

Company Stage

Series B

Total Funding

$66.1M

Headquarters

New York City, New York

Founded

2015

Overview

Headout connects travelers with local experiences and attractions in cities worldwide. The platform allows users to discover and book a variety of activities, such as theme park visits, city tours, and cultural experiences, by partnering with local tour operators and experience providers. This makes it easy for travelers to find memorable experiences with just a few clicks. Headout operates on a commission-based revenue model, earning a fee from local providers for each booking made through its platform. This aligns the interests of Headout with its partners, promoting increased bookings and customer satisfaction. The platform enhances the user experience by offering real-time availability, instant booking confirmations, and live chat support with local experts, ensuring travelers can plan their activities confidently and easily. Headout's goal is to transform urban experiences by providing seamless access to the best local activities and attractions.

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Simplify's Take

What believers are saying

  • Headout's expansion to 500 cities will increase its global reach and customer base.
  • The rise of 'bleisure' travel creates new opportunities for curated business traveler experiences.
  • AI integration enhances customer service and personalization, meeting traveler expectations.

What critics are saying

  • Increased competition from platforms like Tiqets could dilute Headout's market share.
  • Integration challenges with Dabble may delay AI feature rollouts, affecting user experience.
  • The 'Drops' feature might reduce profit margins if not managed carefully.

What makes Headout unique

  • Headout offers real-time availability and instant booking confirmations for seamless travel planning.
  • The platform connects travelers with local experts for personalized experiences.
  • Headout's commission-based model aligns its interests with local providers.

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Funding

Total Funding

$66.1M

Above

Industry Average

Funded Over

4 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

-1%

1 year growth

0%

2 year growth

1%
Ausleisure
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.

House of Creators
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.

PhocusWire
May 31st, 2024
Tours And Activities Platform Headout Acquires Dabble To Build Ai Experiences

Headout, the New York-based tours and. activities marketplace, has acquired Dabble,. a Y Combinator-backed startup that creates solutions to bridge the digital and physical

Botpresso
Jul 31st, 2023
A data-driven Campaign to boost organic revenue by 1081.2%

Headout, partnered with Botpresso to enhance their online presence and achieve ambitious goals of increasing organic traffic and revenue by 200%.

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