Headout

Headout

Connects travelers with local experiences

About

Headout connects travelers with local experiences and attractions in cities worldwide. The platform aggregates a variety of activities, such as theme park visits, city tours, and cultural experiences, making it easy for users to discover and book these experiences online. By partnering with local tour operators and experience providers, Headout offers over 10,000 activities, ensuring a wide selection for tourists. The company operates on a commission-based model, earning revenue when customers book experiences through its platform, which aligns its interests with those of its partners. Headout enhances the user experience by providing real-time availability, instant booking confirmations, and live chat support with local experts, allowing travelers to plan their activities confidently and conveniently. The goal of Headout is to transform urban experiences by making it simple for travelers to access the best local activities.

Company Stage

Series B

Employees

501-1,000

Industries

Consumer Software, Consumer Goods

Total Funding

$63.9M

Headquarters

New York City, New York

Founded

2015


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Simplify's Take

What believers are saying

  • Headout's expansion to 500 cities is fueled by a recent $30M Series B funding.
  • The rise of 'bleisure' travel creates new opportunities for unique business-leisure experiences.
  • Increased demand for personalized travel experiences supports Headout's technology-driven approach.

What critics are saying

  • Increased competition from platforms like Airbnb Experiences and Viator threatens market share.
  • Dependence on third-party providers may lead to inconsistent experience quality.
  • Potential backlash from overtourism could result in restrictions on certain experiences.

What makes Headout unique

  • Headout offers real-time availability and instant booking confirmations for seamless travel planning.
  • The platform connects travelers with over 10,000 curated experiences worldwide.
  • Headout's commission-based model aligns its interests with local experience providers.

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Growth & Insights
Headcount

6 month growth

3%

1 year growth

9%

2 year growth

54%

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.

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