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      Headout

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      Headout Reviews

      4.2

      87% would recommend to a friend

      (261 total reviews)

      Varun Khona

      94% approve of CEO

      86% positive business outlook

      Ratings by category

      4.4

      Culture and values

      4.2

      Work/Life balance

      4.1

      Diversity and inclusion

      4.1

      Senior management

      4.1

      Compensation and benefits

      4.1

      Career opportunities

      Headout has an employee rating of 4.2 out of 5 stars, based on 261 company reviews on Glassdoor which indicates that most employees have an excellent working experience there. The Headout employee rating is in line with the average (within 1 standard deviation) for employers within the Information Technology industry (3.9 stars).

      Ratings by demographic groups

      Reviews by job title

      261 reviews
      5.0
      6 May 2026

      Empowering role with steep learning curve, but requires hustle

      Senior manager - founders office
      Recommend
      CEO approval
      Business outlook

      Pros

      1. Extreme leverage and ownership of the problem in your role & beyond -that gives an outsized compounding impact. This role is - "if you see it, fix it" energy. 2. You are at the forefront of the AI - creation & adoption. 3. Travel as an industry, after COVID, is an upward trend. And, Headout is one of the fastest-growing companies to be part of. 4. Learning density is insane in a central role; you work with 15+ market teams at once. One quarter here teaches what two years at any other company would. 5. Culture & people is genuinely the strongest part. This is what keeps you here. Leadership actually cares about yours & everyone growth within the company.

      Cons

      Cross-functional influence runs on relationships, not processes. Getting things done across teams depends on hustle and timing. Good for natural influencers, harder for everyone else.

      Viewing 1 - 3 of 261 Reviews
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      Glassdoor has 300 Headout reviews submitted anonymously by Headout employees. Read employee reviews and ratings on Glassdoor to decide if Headout is right for you.