Roboflow’s Cancun Offsite: Big Ideas and Bigger Savings in Paradise

Our Client

Roboflow is a fast-growing computer vision startup that provides a platform for developers to create, train, and deploy machine learning models for visual data. The company, founded in 2019 by Joseph Nelson and Brad Dwyer, builds tools to help software developers and enterprises across industries develop computer vision applications. Its mission is to make computer vision easy and accessible – a goal that has attracted a large community of users.

Roboflow has become a key player in democratizing access to computer vision technology. Its platform supports tens of thousands of developers across industries, offering solutions that scale from rapid prototyping to production-grade deployments. With a commitment to enabling faster and more efficient machine learning workflows, Roboflow continues to innovate at the intersection of software and visual data.

Setting the Stage in Cancun

Roboflow’s offsite took place at Club Med Cancun, where the team gathered for a multi-day program designed to blend collaborative work with relaxed beachfront surroundings. While the resort offered a wide range of amenities—including multiple restaurants, organized group activities, and easy access to the beach—the experience presented some operational challenges that required close coordination behind the scenes.

Despite limitations with on-the-ground support and certain aspects of the venue’s readiness for group events, Offsite worked proactively to ensure Roboflow’s agenda remained intact. From securing a private welcome reception to managing team dinners and programming transitions, Offsite handled the logistics to prevent venue shortcomings from impacting the overall flow of the retreat. The result was a cohesive gathering focused on team alignment, structured planning, and shared progress.

Hacking, Bonding, and Beachside Fun

Each day in Cancun struck a balance between focused collaboration and carefree bonding. Mornings kicked off with team meetings in the private conference space, where Roboflow’s leaders set the vision and teams dived into a company-wide hackathon. With Offsite handling all the A/V, scheduling, and room setup details, the Roboflow team could simply plug in their laptops and collaborate.

The retreat agenda (developed in partnership with Offsite) was packed with productive sprints. Teams formed “initiative hacking” groups working on mission-critical projects ranging from improving product features to brainstorming new customer solutions. For example, engineers and product managers huddled to speed up model inference, while others built a prototype job board for the computer vision community – all part of Roboflow’s goals to drive innovation. These work blocks were interspersed with updates from team leads and eventually culminated in a “Ship & Tell” session, where each group proudly demoed what they had built during the week. The energy in the room during these demos was electric – being together in person clearly sparked creativity and rapid problem-solving that would be hard to replicate over Zoom.

Offsite also wove in deliberate fun to ensure the week wasn’t all work. One of the mid-week highlights was a beach Olympics team-building challenge. On Wednesday, the Offsite crew turned a stretch of white-sand beach into an “arena” for lighthearted competition. 

Evenings were reserved for relaxation and connection. Offsite coordinated group dinners at the resort’s top restaurants so the team could unwind together after busy days. On Tuesday, they savored a private dinner at La Estancia, the on-site steakhouse, enjoying tender cuts and toasts to the day’s accomplishments. Wednesday and Thursday featured dinners at The Hacienda, a restaurant with an outdoor terrace where the group could feel the ocean breeze as they dined. Offsite’s planning ensured the reservations, private sections, and set menus were all handled in advance – the Roboflow crew simply showed up to great food and company. After dinner, attendees were free to explore the resort’s nightly entertainment (some caught live music and shows) or return to the meeting lounge for more laid-back hangouts. By blending structured hackathon time with ample opportunities to relax and have fun, the retreat achieved its goal of uniting the team and reinvigorating everyone for the road ahead.

Navigating On-Site Challenges

No offsite is without its hiccups, and this retreat had its share of unforeseen challenges – but Offsite’s team was there every step of the way to tackle issues head-on so that Roboflow didn’t have to. Some operational aspects proved challenging once the event was underway. Gaps in coordination between planning contacts and on-site staff created minor disruptions that required real-time adjustments during the retreat. Despite these hurdles, the event proceeded without disruption to Roboflow’s programming—due in large part to Offsite’s proactive management and experienced oversight.

Offsite remained in close communication with both resort staff and the Roboflow team, anticipating needs and troubleshooting issues in real time. From rebooking transportation to addressing last-minute adjustments to room logistics, Offsite’s support team absorbed the operational burden to ensure Roboflow’s attendees remained focused on their work and team connection. Despite the on-site challenges, the retreat was carried out smoothly—testament to the value of experienced logistical planning and vendor oversight.

Flexibility was another key asset Offsite brought to the table. Roboflow opted to extend the retreat by three additional nights to allow employees’ partners to join for a relaxed weekend following the core programming. Offsite smoothly adapted to the change—securing the necessary accommodations, coordinating the new timeline, and ensuring the venue could support the extended stay. No formal programming was required for the guests, and Offsite did not charge additional planning fees for the added attendees. To enrich the experience, a group excursion to Isla Mujeres was arranged, providing a shared opportunity for relaxation and sightseeing. The result was a well-integrated extension that felt effortless to participants and logistically sound for organizers.

Big Savings and Lasting Impact

Roboflow’s Cancun offsite was not only a rejuvenating team experience – it was also a huge win for the company’s budget. Offsite’s expertise in vendor negotiation and cost-efficient planning delivered tremendous savings. By negotiating significant discounts on accommodations, transportation, and per-attendee fees—and by absorbing the logistical impact of additional guests—Offsite achieved total savings of over $57,000 for Roboflow. The contracted hotel rate alone accounted for more than $35,000 in savings compared to standard pricing, and further reductions were secured across transportation services and planning labor. Notably, the extended stay and inclusion of plus ones were handled without passing added costs to the client, thanks to preemptive coordination and the absence of formal programming requirements. As a result, the overall spend per participant remained under Roboflow’s original budget expectations, even after factoring in additional days and guests.

These financial efficiencies were not achieved at the expense of the team’s experience. On the contrary, they enabled Roboflow to redirect focus toward the strategic and interpersonal objectives of the retreat. Attendees engaged in uninterrupted working sessions, initiative development, and informal bonding time—all without being burdened by logistical friction or concerns about budget overruns. Offsite’s careful stewardship of resources not only preserved program quality but also ensured leadership could concentrate on internal alignment and cultural continuity. The event demonstrated that with the right partner, meaningful offsites can be delivered with high impact and financial discipline—an outcome that further solidified Offsite’s position as a trusted planning resource for Roboflow’s future team gatherings.

Continuing the Collaboration

Despite the logistical setbacks, Roboflow’s leadership expressed interest in maintaining a continued partnership with Offsite for future team gatherings. The success of previous events, combined with the substantial cost savings and operational relief delivered during this retreat, reinforced Offsite’s value as a dependable planning partner.

As Roboflow continues to grow and scale its internal programming, the company is exploring options for future cadence-based retreats and additional support offerings. Offsite remains well-positioned to assist with these evolving needs, whether through expanded event services, vendor negotiations, or on-the-ground execution. The foundation built through this engagement signals a continuing collaboration—one grounded in trust, efficiency, and a shared commitment to impactful team experiences.