WeRoad US Group Leader

Posted Yesterday
Be an Early Applicant
Milano, ITA
In-Office
Entry level
Consumer Web • Software • Travel • Hospitality
The Role
Lead small-group adventure trips worldwide on a per‑trip basis. Manage group dynamics for 10–15 travelers, set the tone, run activities, handle logistics and unexpected issues, and ensure an inclusive, high-energy experience. Participate in a two-day Selection Weekend as part of the hiring process.
Summary Generated by Built In

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 Selection Weekend: If your application stands out, we’re inviting you to the Selection Weekend*, a high-energy, 2-day interview process. It’s part connection, part challenge, and 100% WeRoad. Show us you can lead the pack, and you’re in.

*Note: for the Selection Weekend, accommodation, saturday dinner and sunday breakfast will be covered by WeRoad.

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

Skills Required

  • Ability to lead groups of 10-15 travelers on multi-day trips
  • Be physically present on trip and available to travel internationally
  • Strong social intelligence and group facilitation skills
  • Resourcefulness and crisis-management/problem-solving under changing conditions
  • High energy, adventurous, empathetic personality who loves meeting new people
  • Available to work per-trip (flexible, part-time/freelance commitment)
  • Attend the 2-day Selection Weekend as part of the selection process
  • Alignment with WeRoad's vision and values
  • Preferred age range: in your 20s–30s
Am I A Good Fit?
beta
Get Personalized Job Insights.
Our AI-powered fit analysis compares your resume with a job listing so you know if your skills & experience align.

The Company
0 Employees
Year Founded: 2017

What We Do

WeRoad is a Milan-based travel‑tech company that designs curated small‑group adventure trips and community experiences for solo travellers (Millennial and Gen‑Z cohorts). Using an asset‑light marketplace, local DMC partners and a decentralized network of travel coordinators, WeRoad curates immersive itineraries worldwide and connects travellers year‑round via community products like the WeMeet app and B2B partnerships.

Similar Jobs

InterSystems Logo InterSystems

Senior Project Manager

Artificial Intelligence • Big Data • Healthtech • Machine Learning • Software • Database • Analytics
Easy Apply
In-Office
Milano, ITA
2407 Employees

Pfizer Logo Pfizer

Platform Engineer

Artificial Intelligence • Healthtech • Machine Learning • Natural Language Processing • Biotech • Pharmaceutical
In-Office or Remote
36 Locations
121990 Employees
65K-109K Annually

Datadog Logo Datadog

Staff Software Engineer

Artificial Intelligence • Cloud • Security • Software • Cybersecurity
Easy Apply
Remote or Hybrid
5 Locations
6500 Employees
Remote or Hybrid
Italy
897 Employees

Similar Companies Hiring

Hanover Park Thumbnail
Artificial Intelligence • Fintech • Software • Financial Services
New York, New York
42 Employees
Kepler  Thumbnail
Fintech • Software
New York, New York
6 Employees
Onshore Thumbnail
Artificial Intelligence • Fintech • Software • Financial Services
New York, New York
60 Employees

Sign up now Access later

Create Free Account

Please log in or sign up to report this job.

Create Free Account