How to Plan a successful company offsite for a remote team in Costa Rica

We sat down with Janina Asprilla, who played a key role in shaping and delivering the company’s offsite. She shares how the team brought together a global remote workforce for an in-person retreat designed to strengthen alignment, connection, and company vision.

1. About Your Company

1.1 Could you tell me about your company? What does your company do?

We are a global digital asset education and investment company focused on helping individuals build wealth through decentralized finance and alternative financial strategies. 💡💰

We provide structured education programs, mentorship, and investor-focused infrastructure to a community of 4,000+ members worldwide. Alongside education, we are expanding into software and investor ecosystems to support long-term wealth creation and financial sovereignty.

1.2 Is your company fully remote?

Yes, we are fully remote. 💻

Our team operates globally across multiple time zones, with leadership primarily based in the UAE and Europe, and team members across North America, Europe, Asia, and LATAM. 🌍

1.3 What is your company size?

We are a team of 120+ employees

2. Offsite Planning Background

2.1 What prompted you to organize an offsite event? Who initiated it?

As a fully remote company, we recognized the need to strengthen in-person alignment, deepen leadership trust, and reinforce company vision at scale. 🤝

The initiative was driven by our founders and leadership team, with the objective of accelerating growth, improving cross-functional collaboration, and strengthening cultural cohesion across departments. 🚀

2.2 How long / how many months did you spend planning it?

We spent approximately 3-4 months planning the offsite.

This included destination selection, budgeting, logistics coordination, accommodation sourcing, programming design, team alignment, and vendor management to ensure both operational efficiency and a high-quality experience.

2.3 How often do you plan company offsites?

We plan structured company offsites annually, with additional smaller leadership or departmental retreats throughout the year, depending on strategic needs and growth phase.

3. Destination & Venue Choice

3.1 Why did you choose Costa Rica and Marriott Los Suenos Hotel?

We chose Costa Rica because we wanted a destination that combined accessibility from North America with a strong natural environment that encourages connection, reflection, and team bonding. 🌴☀️

The Los Sueños Marriott stood out due to its resort-style setup, ability to host a larger group in one centralized location, strong on-site amenities, and dedicated event infrastructure. Having accommodation, conference facilities, and social spaces integrated into one property was a major decision factor for us.

3.2 Can you please provide me with an overview your off-site?

The offsite was a retreat designed to strengthen alignment, clarify company vision, and improve cross-functional collaboration.

The program included:

1. C-suite and leadership presentations 🎤
2. Informal connection time and social activities 🍹
3. Team-building experiences 🤝
4. C-suite extra days for leadership sessions 🧠

We aimed to balance structured strategy sessions with downtime to allow for organic relationship-building and reflection.

4. Objectives & Success Metrics

4.1 What key performance indicators (KPIs) or objectives and key results (OKRs) did you set for this offsite?

Our primary KPIs were centered around alignment and connection rather than financial metrics.

Specifically, we aimed for:

1. Increased alignment with the company vision and long-term mission
2. Stronger personal connection between team members across departments
3. Deeper engagement with the founders and leadership team
4. A strengthened sense of shared purpose, regardless of role or seniority

As a fully remote company, we believe that in-person interaction plays a critical role in culture-building. It was important for team members to not only understand the strategic direction, but to truly feel connected to the people behind it.

4.2 What was the primary goal of the retreat, and how successful were you in achieving it?

The primary goal of the retreat was to create a deeply connected leadership and management environment, one where everyone felt aligned, valued, and united under the same mission.

We wanted people to experience the company culture in person, build real relationships, and feel inspired by direct interaction with the founders.

We successfully achieved this. The post-event feedback was overwhelmingly positive. Team members highlighted the energy, the culture, the quality of the presentations, the activities, and the overall experience. Many described it as one of the most impactful experiences they’ve had.

Most importantly, people left feeling more connected, not just to the company’s strategy, but to each other.

5. Experience with Retreat

5.1 In what ways has Retreat supported or enhanced your planning and experience?

Retreat played a key role in making this offsite possible and significantly easing the planning process. From destination sourcing to venue coordination and contract support, their involvement streamlined what would otherwise have been a very complex logistical undertaking.

Zeineb, in particular, was exceptional. Her responsiveness, attention to detail, and proactive communication made a substantial difference throughout the planning phase. She consistently went above and beyond to support us, provide clarity, and help navigate negotiations and vendor coordination.

Given the scale of our group and the level of detail required, her guidance was invaluable. We genuinely could not have executed this offsite at the level we did without her support.

Her professionalism and dedication made her feel like an extension of our internal team rather than an external partner. ✨