The Role: Leading small group adventures around the globe.
The Commitment: Per-trip. Perfect for your vacation days or freelance life.
Location: Anywhere but an office. The World! ?

Our Vision: Connecting People, Cultures, and Stories.

This is why we exist. At WeRoad, we don’t just book flights; we bridge worlds.

We’re on a mission to kill the digital disconnect and get people back into the real world. We take groups of strangers and turn them into a "wolfpack" through shared experiences and a bit of grit. After building a community of 5,000+ leaders in Europe, we’re finally launching in the States.

(Watch the video to feel the energy of the Global Community)

What is a WeRoad Group Leader?

First things first: This is not a desk job. It’s also not a full-time career. It’s a passion project for people who live to travel.

You keep your 9-to-5, your freelance hustle, or your creative grind. When you’re ready to escape, you pick a WeRoad trip and lead it.

- You are on the ground: You’ll be physically on the trip—navigating the streets of Tokyo, hiking in Iceland, or catching sunsets in Baja with a group of 10-15 travelers.

- You are the Soul of the trip: You aren't a tour guide reading from a script. You’re the person who sets the tone, breaks the ice, brings the group together and makes sure everyone feels included.

- You’re the Fixer: When a flight is delayed or a plan changes, you don’t sweat it. You pivot and keep the energy high.

Who we’re looking for

This is for the natural-born leaders.



The ones who are always "the planner" in their friend group.

- Social Intelligence: You can read a room and handle group dynamics like a pro.

- Resourcefulness: You’re grounded and practical. You find solutions while others are still looking for the problem.

- Energy: You’re adventurous, empathetic, and genuinely love meeting new people.

Who should apply

We’d love to hear from you if you:

- Are in your 20s, 30s

- Love group experiences and human connection

- Feel aligned with WeRoad’s vision and values

The Perks

- Travel the World: While you’re leading a trip, the experience is on us. We handle the flights, the stays, and the itinerary. You bring the energy; we provide the world.

- The Global Community: Gain instant access to our worldwide community of thousands of leaders.

- Master Leadership: This is a real-world masterclass in crisis management and people skills that you just can't get in a cubicle.

How the selection process works

We don’t do boring HR interviews. We want to see your energy in action.

1. The Application: Show us your vibe. We want to know you!

2. The Bootcamp (May 16-17): If your application stands out, we’re inviting you to Austin, Texas. The Austin Bootcamp* is a high-energy, 2-day selection event. It’s part connection, part challenge, and 100% WeRoad. Show us you can lead the pack, and you’re in.

*Note: for the Austin Bootcamp, accommodation and other inclusions will be explained when relevant

Ready to lead the world? Read the vision. Catch the vibe and apply!

📌 WeRoad US Group Leader (Milano)
🏢 Società riconosciuta
📍 Milano