Be An Unsettled EXPERIENCE Leader

 Medellín, Colombia

Positions Available Starting July 2022 
Application Deadline: April 30, 2022

Do you have a background in facilitating personal and professional development? Feel most alive when working in a high-energy, group dynamic? Want to help people expand their possibilities through intentional living and shared experiences? Do you love where you live in Medellín? 

If you love building community, connecting people to their passions, and curating remarkable shared experiences in a fast-paced environment, then read on. Unsettled is hiring an Experience Leader to run our month-long retreats in Medellin, Colombia. 


Unsettled is a travel company for those who embrace the unknown and value meaningful human connection. Who believe that feeling a little bit “unsettled” is a positive impulse for change, innovation, and exploration.

We curate travel experiences, adventures, and programs for today’s professionals who seek to take their work, life, and growth beyond traditional borders. Unsettled’s retreats and programs are created for entrepreneurs, creatives, independent workers and professionals in transition and are uniquely designed to help people connect more deeply to their lives, chart uncharted territory, and bring their ideas and dreams into fruition.


Unsettled Experience Leaders are the conductors, facilitators, planners, hosts, guides, and companions for curated groups of 15 – 25 highly creative and talented professionals from around the world.

The primary role of an Experience Leader is to “run the show”, by providing facilitation and support for participants during these travel experiences and programs. You will wear many hats, from the problem-solving and customer service required of hospitality to the facilitation required of running in-depth workshops. At times this role takes the endurance of an Olympian, and that excites you.

We are seeking a candidate who is Colombian and lives and loves Medellín. You will run our month-long retreats in Medellin 3-5 months out of year. During these months you will work at or near full-time for Unsettled. 


A GIFTED FACILITATOR. You have multi-year experience facilitating workshops related to work / life transition, career changes, goal setting, skill assessment and development, personal narrative and branding. You are comfortable leading a group of high achieving adults through workshops, frameworks, and engaging sessions.

A NATURAL MENTOR. You care deeply about seeing people succeed and grow. You know how to support and challenge people in the right ways. You can meet them where they are to take them where they want to go. You are as connected to the infinite field of possibilities are you are to a tried and tested tool kit of coaching and mentoring skills.

ENDLESS ENERGY. You get energy from people and you endlessly want to be around people. It doesn’t matter if you’re running a workshop, going out after dinner, or staying in for the night, you want to be where the action is. You’re not above the late nights or administrative work because you know what it takes to create the kinds of experiences that Unsettled is known for. It takes your endless amounts of energy.

A MULTICULTURAL CUSTOMER-ORIENTED PROFESSIONAL. You know what it takes to succeed in hospitality. You constantly have to earn the respect of the customer. It’s a nonstop job, and you have the professional experience in travel or hospitality that’ll help you succeed from day one. You’re proud of your experience in high end restaurants, hotels, and bars. You’re obsessively customer oriented; always working to manage and exceed their expectations.

A COMMUNITY CREATOR. You are an experienced community builder. All your life, you have guided people into the unknown — be it spiritually, physically, or mentally. You are a keen observer and are always looking for opportunities to build strong relationships, positive group dynamics, and meaningful discussions.


Experience Leader responsibilities includes:

  • Implementing the core Unsettled experience, by planning and facilitating workshops, welcome activities, reflection opportunities, local field trips, and more.
  • Coordinating and planning with our Location Managers to ensure a seamless experience for participants.
  • Leading by example, and living by the value set that is the bedrock of our community’s culture.
  • Communicating actively, openly, and honestly with participants, staff, and partners. You have the foresight to predict when conflicts, group dynamics, or problems arise and solve them in real time, before they escalate.


Pre-Trip Responsibilities:

In the months weeks leading up to a program, you will be responsible for:

  • Providing pre-departure support to participants via a variety of our communication tools
  • Reviewing participants information to identify patterns, themes, and opportunities for the month
  • Developing unique original content for transition, professional, and personal development programs.
  • Coordinating with the Location Manager in your destination and your supervisor at Unsettled to plan, organize, and execute on necessary planning tasks

Experience Responsibilities:

During the program, you will be responsible for:

  • Facilitating and running our core program and activities
  • Working closely with Unsettled’s Location Manager to plan, organize, and problem solve for upcoming events and ongoing operations
  • Finding and highlighting opportunities for growth, local immersion, and adventure for Unsettled participants
  • Reading individual and group dynamics on the fly and addressing the needs or challenges of participants as soon as they arise, if not earlier
  • Positively and actively facilitating discussions and organized learning, and supporting individual participants when they organize user-led workshops and activity
  • Managing and tracking experience expenses and handling administrative tasks for recording the details of the month

This is a full-time position while you are running a program (though not a full-time position year round). During a program, you can expect to be on call at odd hours and days throughout the month. However, if you manage your time and set expectations well, you will have time to yourself throughout the month and will have many of the benefits of participants — spending time with a community, experiencing new places, enjoying adventures, and growing along with them.


  • 5+ Years experience in training, program facilitation, or similar field related to personal or professional development.


  • 5+ Years experience in the hospitality industry or leading travel experiences for a similar professional target market


  • Exceptional event planning, running the front stage of an event, and organizational skills
  • Experience building and growing diverse communities
  • Proven ability to work in diverse cultures, environments, and with staff from different backgrounds
  • Comfortable and experienced working in remote environments
  • Fluent in English, with conversational abilities in at least 1 other language
  • Ability to travel for 6-8 months out of the year, with long stretches on the road
  • Extra consideration given for any formal certification in coaching or training



This is a journey into the unknown, and, if you are willing to dig in and put in the work, it can be a transformative journey for both you and our participants. Direct benefits include:

  • Monthly compensation of 6,000,000 to 8,000,000 COP commensurate according to applicant’s experience
  • Coverage of costs towards your coworking space, local adventures, field trips, phone data, etc. 
  • Joining an incredibly passionate and fast growing team executing on a truly global vision



Please email with your CV and a cover letter answering two of the following questions:

(1) Tell us the details of what you’ve done in your work that’s most relevant to this position. We’re not as interested in your position titles as much as we are in learning about what you did, how often you did it, and why it’ll help you succeed at Unsettled.

(2) Take a moment, and imagine yourself in this role. Tell us how you see yourself being successful on the ground. How are you uniquely positioned to succeed in this role? And what does that look like for you related to the specific duties?

(3) Tell us the last time you led a group (in travel, teaching, a workshop, etc.). What was your style? What extra value did you personally bring to the participants? Provide details: How did you organize and prepare? What challenged you?

We will interview the most competitive applicants, and regret that we cannot reply directly to everyone who applies. Early applicants will be given priority. 

So. Think you’ve got what it takes?


Our Impact

“Unsettled is more than travel, it’s more than a work trip, it’s a life-affirming experience where I got to explore who I am and who I want to be in the world. My Unsettled cohort encouraged me, listened to me, challenged me, reflected myself back to me, gave me space to grow, and cared for me. I’ve never laughed so much in one month! I returned from my experience with new-found strength, resilience, and peace, and with some what I hope will be life-long friends.” – Tanya

Stories from our community

At the heart of Unsettled lies thousands of stories. Stories of people who embrace the unknown, challenge themselves, and push beyond their own boundaries. These stories span the breadth of the human experience, and get to the heart of what it means to be human today – to live boldly, no matter what that looks like for each of us….

Unsettled is a global community for those who live and work differently. 

Growth | Meaning | Adventure