How FLEX Strengthened Team Connections at Their Offsite

Our Client

Flex, an early-stage, remote-first fintech startup, is redefining how rent is paid in the U.S. Founded in 2019, Flex allows renters to split monthly rent into smaller payments throughout the month—improving cash flow, avoiding late fees, and supporting financial stability.

The platform benefits both renters and property managers. Renters gain flexibility and control, while property managers receive on-time payments and increased resident satisfaction. Flex integrates easily with existing systems, enabling smooth adoption across multifamily properties.

Headquartered in New York with teams distributed globally and backed by leading investors, Flex is used by renters nationwide. As financial pressures grow, Flex is modernizing rent—making it more manageable, predictable, and renter-friendly.

Hosting an Offsite for a Remote-First Company

As a remote-first company, Flex recognized the unique value of gathering their globally distributed team in person. The company’s rapid growth and distributed structure made face-to-face interaction essential for fostering team cohesion and alignment on strategic goals. 

Coordinating an offsite event for 215 people posed logistical complexities—from securing accommodations to planning activities that would engage a diverse team. Flex envisioned an experience that was both purposeful and energizing: a chance to celebrate, connect, and realign around a shared mission.

Choosing to Work With Offsite

Given the complexity of organizing an offsite event of this scale, Flex partnered with Offsite to manage the event logistics comprehensively. Leveraging Offsite’s curated marketplace, the team secured premium group rates and a highly accommodating venue at the Grand Hyatt Playa del Carmen. Offsite managed all aspects, including vendor coordination, accommodation bookings, and on-site activities, ensuring a hassle-free experience for Flex’s internal team.

The partnership allowed Flex’s leadership and team to focus on participation and engagement, knowing that all logistical components were expertly handled by Offsite’s professional team.

Rebuilding Trust and Fostering Connection

Flex’s offsite was designed to strike a thoughtful balance between strategic alignment and authentic relationship-building. Company-wide sessions led by executives provided transparency into vision and priorities, while facilitated workshops invited input and collaboration across departments.

Outside of structured programming, team members took part in a “Choose Your Own Adventure” afternoon, with options like cenote swimming, bike tours, cooking classes, and exploring local attractions—each curated to offer both enjoyment and spontaneous connection. A dedicated DJ created a relaxed and enjoyable atmosphere during evening events, encouraging informal interactions and deepening team relationships.

Throughout the offsite retreat, team members strengthened interpersonal connections, improving communication and trust—essential components for a remote-first environment.

Looking Ahead

The 2024 retreat marked a meaningful cultural milestone for Flex. The positive feedback and tangible benefits of the offsite retreat demonstrated the substantial value Offsite provides companies that are seeking to enhance their culture and internal cohesion through expertly managed retreats.

Developing an Offsite Cadence

Flex’s offsite experience showcased the impact of well-orchestrated, intentional retreats. As the company continues to grow, the leadership team is now equipped with a successful model for planning future gatherings that drive cultural alignment and team connection. With Offsite’s proven support, Flex is well-positioned to explore a sustainable cadence of offsites that keep their global team engaged, united, and focused on shared success.