Client:
Pilot (Internal Team Retreat)
Objective:
Immerse the team in the kind of authentic travel experience their users love, while building team alignment and strategic clarity for the year ahead.
The Story:
Here’s the thing about building a travel product: to create something truly user-first, you have to travel like your users. The Pilot team came from different backgrounds, different countries, and had plenty of traveling experience on their own. But they have never dove into the kind of immersive, sometimes chaotic, always memorable adventures together.
For the Pilot team this wasn’t a vacation. It was research, inspiration, and internal alignment wrapped into one unforgettable experience.
With a small team split between Vancouver and Toronto, the leadership knew that in-person time was rare and valuable. So instead of boardrooms and post-its, they opted for backpacks and hostel check-ins. The 10-day retreat was held in Medellín, Colombia, and it gave the team exactly what they needed: direct insight into their target audience and the clarity to build a better product in the months ahead.
“This wasn’t just a team offsite. It was us becoming our users for 10 days.”
The Goals:
- Gain first-hand insight into how travel actually unfolds for their target user base
- Use lived experience to identify product gaps and new opportunities
- Align on goals and roadmap for the upcoming year
- Strengthen team trust and cohesion
But traveling as a remote, international team wasn’t without its challenges. Citizenship and visa statuses varied, requiring extra coordination, and two team members had to fly out a day early. And like any lean startup, they had a tight budget and big goals.
The Experience:
Pilot designed the itinerary to reflect what their community of travelers might plan: Staying in multiple locations, local experiences over tourist traps, and enough structure to keep things flowing while allowing the team to chase the adventure.
They stayed across three locations in El Poblado, Medellín:
- Selina Medellín & Cowork (Day 1–2)
- Los Patios Hostel Boutique (Day 3–5)
- Masaya Medellín (Day 6–9)
From coworking sessions at WeWork to wandering Provenza’s leafy streets, the retreat balanced productive planning days with immersive exploration. Team dinners were held at neighborhood favorites like Mondongo’s and El Altar Taquería, while afternoons were filled with food tours, graffiti walks in Comuna 13, and a full-day trip to Guatapé, a lakeside town nestled in Colombia’s countryside.
One team member had never been out of North America. Another discovered they had a surprising knack for find amazing tacos. From trying street arepas to surviving a rowdy van ride, the journey was messy in all the right ways.
“We learned who the best dancers were, who could handle spice, and who needed a nap after one Llulada. It was bonding, for real.”
The Results:
Strategic Alignment:
In between tours and café stops, the team carved out two structured planning days. That time created clarity and alignment that carried through the rest of the year, unlocking stronger growth and more intuitive product features.
User Empathy:
By living the same style of travel they design for, the Pilot team walked away with pages of insights. The got a deeper view of onboarding pain points and customer journeys. The developed feature ideas sparked while booking day tours on the fly.
Team Culture:
Prior to the trip the team was close, the product of a strong culture. However, this became a team that connected with each other in a way that build unwaivering trust. And it showed up in how they worked afterward.
Efficiency:
With all logistics pre-planned using Pilot’s own tools and templates, the team saved over 75 hours in executive ops and decision fatigue.
“We came back energized and aligned—with stories to tell, and a stronger product to build.”
A Memorable Experience:
- Laughing in the streets of Comuna 13
- Brunches that turned into brainstorms
- Late-night hostel rooftop hangouts
- The pool party where half the team became DJs
- Embracing moments, laughing about it, and loving every second
“You learn a lot about someone when you experience life together.”
For Pilot, this retreat wasn’t just a team trip. It was a product lab. A culture boost.
And a reminder that great things happen when people explore the world together.