General Manager – North America

Why Headout?

What we do is important

In an increasingly digital world, there is a desperate need to augment our human experience by getting us to interact with the real world around us and the people in it. At Headout, our mission is to be the easiest, fastest, and the most delightful way to head out to our next real-life experience. We do this by running a managed marketplace to the world’s most exceptional real-life experiences — from immersive tours to museums to live events and everything in between.

We’ve got scale, fast growth, and solid fundamentals

Headout has served tens of millions of guests from 196 countries on one of our experiences across 70+ cities in 9 languages. Today, we’ve sales in 100s of millions of $s a year and have grown 4x+ in ’22. Contrary to the norm, we deliver this scale and growth while being profitable. We raised $42M in ’22 and have a decade+ runway enabling us to think truly long term.

Now is the right time

While we have a fast-growing business, we are still very early in our journey with a large upside to capture and have a team that is small enough for you to have an indelible outsized impact on our journey. We are not too early, we are not too late.

Our culture

Every place has its own beat and we are no different. We are not the right place for everybody but we are the right place for a certain group of people. Read more about it here.

The role

The GM of North America is at the heart of all things Headout in the region – from strategy to sales, to partnerships, to marketing, to PR, to legal, to finance and everything in between. In this role, you will be the primary voice and ambassador of our North America business. You will be responsible for building a team of 30+ and growing our business to 100s of millions of dollars within the next 24 months. This role requires someone who is strategic, moves fast, detail-oriented, and is a proven team leader.

This job is a high-stakes poker game and the buck stops with you. The combination of skills needed makes this an especially hard role to find the right person. Therein lie the challenges and the opportunity.

What makes this role special?

  • Build. You’ll have your fingerprints all over Headout’s presence in the region. You’ll do whatever it takes to launch quickly, get 1% better every day, and scale something completely new. This means everything from high-level strategy to nitty-gritty operational details – from what cities or regions to launch next, to something as specific as ensuring the title of an experience really communicates the essence of it.
  • Lead. Recruit, lead & retain a world-class team of builders and owners. As a leader, you are a culture carrier. The tone starts with you.
  • Own. From first principles, you’ll build and iterate on the optimal strategy & vision for Headout in North America. You will drive growth and directly manage the P&L.
  • Collaborate. You’ll work with a cross-functional team, including engineering, product, design, operations, finance, and marketing to build the business in this part of the world.
  • Manage. This role requires an experienced manager. You will be building and overseeing a large team, responsible for motivating and empowering them to scale the business.

What skills and experience do you need?

  • You are a leader. You have 5+ years of people management experience leading people leaders (managing leaders with direct reports). You know how to create a trust environment by providing ongoing constructive, actionable feedback for your team and fostering an open climate for communication.
  • You solve problems from the first principles. You’re excited to solve problems in innovative ways, and you resist “this is how it’s always been done” thinking.
  • You’re equally comfortable operating at 10,000 feet and 1 foot. You don’t hesitate to get in the weeds and operate at the lowest level of detail, but you’re just as comfortable thinking long-term and inspiring a team. No job is beneath you.
  • You’re unafraid of ambiguity. Rapid change and learning is exciting to you, and you thrive in ambiguous, startup environments.
  • You’re accountable – You want to lead the outcome and positively shape our most important metrics. You have experience leading projects, hitting goals, and succeeding in a team environment.
  • You’re analytical. You let data win arguments, and you’re comfortable pulling your own data in SQL or modelling in Excel.
  • You’re relentless. You roll up your sleeves and do whatever it takes to make things successful.
  • You have 10+ years of experience. You’ve succeeded in high-performance cultures (whether in tech, operations, strategy, consulting, banking, logistics, military or a related experience)

Bonus

  • You have experience starting or scaling a startup that hit some meaningful inflection points.
  • You have a demonstrated interest in things that lie at the intersection of marketplaces, travel, events, people and all things experiential.
  • You have spent a considerable amount of time in the US and really understand the market’s pulse.

EEO statement

At Headout, we don’t just accept differences — we celebrate it, we support it, and we thrive on it for the benefit of our employees, our partners, and the community at large. Headout provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age or disability. During the interview process, if you need assistance or an accommodation due to a disability, you may contact the recruiter assigned to your application or email us at [email protected].

Privacy policy

Please note that once you apply for this job profile your personal data will be retained for a period of one (1) year. Headout shall process this data for recruitment purposes only. Once the relevant job profile is filled or once the time period of one (1) year from the date of the job application has passed, whichever is later, Headout shall either delete your data or inform you that it shall keep it in its database for future roles. In compliance with the relevant privacy laws, you have the right to request access to your personal data, to request that your personal data be rectified or erased, and to request that the processing of your personal data be restricted. If you have any concerns or questions about the way Headout handle your data, you can contact our Data Protection Officer for more information.

Tagged as: Strategy

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