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Headout

Travel experiences marketplace

Headout logo
501-1000 employees
  • B2C
  • Travel
  • Lifestyle
  • Marketplace
  • Entertainment
  • Mobile
Midtown South, New York, NY

Company mission

Headout is on a mission to make travelling more fun & spontaneous.

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Our take

Over 25 million people from over 105 different cities have purchased a ticket for something on Headout, the mobile-first travel experience and activity platform. It’s a digital marketplace where users can browse tickets to leisure activities in their area, and providers can in turn get help filling last-minute slots.

Unlike some travel and hospitality businesses, Headout has already bounced back and surpassed its pre-pandemic revenue (3.1 Yx oY) and growth (3.2 x YoY) levels. The key was to focus on domestic travel, a new vertical it intends to expand in future with new funding on the table. It’s also looking to aggressively grow its footprint to add hundreds of new cities over the coming years, having doubled its business team in 2023.

Headout is in a very comfortable position to do so: every transaction it carries out is profitable, and there’s plenty of runway on its current funding. This means the team can focus on building out new features for both users and providers. The quality of its product will be its key advantage over Airbnb, which has for a while now been developing a competing marketplace.

Freddie headshot

Freddie

Company Specialist at Welcome to the Jungle

Benefits

  • Unlimited mental wellness leaves
  • No ceiling general leave
  • Every quarterly 1-1 includes a `vacation time` item on the agenda to ensure everyone takes breaks proactively
  • 50% off fitness class memberships
  • Wellness programs once a month
  • Online health platform(s) subscriptions
  • Employee Assistance Program. We've got your back
  • $500 `Headout Credits` to, you guessed it, head out to any of our experiences around the world
  • Unlimited `Learning Credits` for paid courses and sessions to aid your learning & growth
  • Access to conferences and meet-ups
  • Community Lunches twice a week across all offices
  • Travel across our 6 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
  • ESOPS: We follow the standard 1-year cliff and 4-year vesting schedule. You can exercise your ESOPs anytime up to 2 years post-termination. For employees who have been at Headout for a continuous period of 2 years or longer, the exercise period will automatically extend to the life of the option i.e. **10 years**.
  • Outside of teams that are remote-first, everyone else will be expected to spend **50% of their time in the office**. 50% doesn't mean spending 2.5 days a week at the office. It is entirely up to the individual and the team to configure what works best for them
  • Non-remote teams will have complete flexibility to **work from anywhere** for extended durations multiple times a year. Longing to work from a beach for a couple of weeks, no problem
  • You can access any of our hub offices at any time
  • Everyone gets a one-time allowance of up to **$250** to set up a productive work environment for themselves outside of the office

Company values

  • πŸ‘‰ Headout > I
  • πŸ‘‰ Move fast, learn faster
  • πŸ‘‰ High standards
  • πŸ‘‰ Together is better
  • πŸ‘‰ Take ownership and initiative

Funding (last 2 of 5 rounds)

Feb 2022

$30m

SERIES B

Sep 2021

$12m

SERIES B

Total funding: $65.7m

This company has top investors

Leadership

Previously founded and served as CEO of travel company Trippy.

Previously a senior member of the technical staff at Oracle.

Worked a spell as a consultant at PTOLEMUS Consulting Group.

Jobs (3)

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Operations & Strategy