You can work with someone for years, message them every day, and still realize you’ve never had a real conversation with them.
That’s one of the tradeoffs of running a remote company. The work gets done, but the context around the work may be missing something. The side conversations, the instant feedback, the relationships that make collaboration smoother over time.
We’ve been fully remote at Vecteezy for years, and overall it’s been a huge advantage. But it’s also forced us to be more intentional about when and how we bring people together in person.
Over the past few years, we’ve come together for an annual company meeting. In September 2025, we took our team to Orlando, our most ambitious event yet. We had 31 of our 56 team members attend in person, while the rest joined remotely. We encouraged people to attend, but didn’t require it. Travel isn’t always realistic, and we didn’t want it to be a source of pressure.
Six team members flew in from outside the U.S. Three traveled from Indonesia, two from Canada, and one from Germany. For some of them, it was the first time meeting coworkers they’d worked with for years.
This article shares what it actually cost to bring everyone together in Orlando, what we noticed once we were all in the same room, and a few things we’ll do differently next time. If you run a remote team and have considered an in-person offsite, I hope this gives you a clearer picture of what the investment really looks like in practice.
What we wanted out of the week
The goal wasn’t just to get everyone in the same place. We wanted people to better understand what other teams actually do day-to-day. Not job titles, but real work. What’s hard about it, where things get stuck, and how one team’s decisions affect another.
We also needed time to talk through where the company is right now. What’s been working, what hasn’t, and what we’re focused on next. It’s easier to have those conversations in a room where everyone hears the same thing at the same time.
Another big part of the week was simply getting to know each other better. Sharing meals, sitting next to someone you usually only see in a Zoom square, having conversations that don’t start with an agenda. That stuff carries over once everyone’s back home.
We wanted to give people a few shared experiences they’d remember. Not forced bonding, just time together that didn’t feel like work.
There was also a practical goal around communication. When you’ve met someone in person, future Slack messages land differently. Tone makes more sense. You’re quicker to give the benefit of the doubt.
Finally, we wanted to create space for the kind of conversations that don’t fit neatly into a scheduled call. Side discussions, quick problem-solving, ideas that come up between sessions. And, honestly, it was also a way to say “thank you” by doing something outside the normal routine.
How the week came together
We started planning the Orlando meeting in early 2025. Until then, our largest in-person gathering had been in Nashville in 2023, about an hour from our headquarters in Bowling Green. Orlando was on a different scale, with more flights, more logistics, and less room for improvising.
The week followed a simple rhythm. The leadership team arrived on Sunday. Monday was split between leadership sessions and travel for everyone else. Tuesday and Wednesday were our full company days. Thursday was set aside for Disney. Everyone headed home on Friday.
Some team members brought family along. Meetings were just for the team, but families joined us for the park day, and people had free evenings to spend time together.
We stayed at the Hilton Orlando Lake Buena Vista in Disney Springs. It was close to the airport, easy to get around on foot, and the Disney shuttles made park transportation simple. Having hotel rooms, meeting space, restaurants, and coffee all within a short walk mattered more than we expected.
Tuesday and Wednesday were structured, but not wall-to-wall. We planned about four to five hours of meetings each day, with breaks and lunch built.
Adam Gamble, our CTO, and I opened with a state-of-the-company session. We covered what had gone well, where things were bumpy, and what we were focused on next. After that came team and department presentations, smaller group sessions, and a few light icebreakers to keep the energy up.
We mixed in some entertainment as a break from the sessions. We arranged for The Dapper Dans from Magic Kingdom to stop by for music and jokes, and a magician did a short set that kept people engaged without feeling like filler.
Breakfast and lunch were catered in the meeting space. On Tuesday night, teams split up and picked their own restaurants around Disney Springs. Wednesday night, we all met at Wine Bar George for dinner.
Thursday was left open on purpose. Each team member received a Park Hopper pass, and discounted tickets were available for families. We also gave out gift cards to cover food in the parks. There was no schedule and no meetings. It was just a day to enjoy.
Cost breakdown
In total, the entire meeting cost $125,293, or $4,041 per attendee. Below is a breakdown of the main categories:
| Airfare | $17,555 |
| VISA Expenses | $1,297 |
| Misc. Travel Reimbursements | $10,515 |
| Airport Shuttles | $1,671 |
| Hotel Rooms | $37,000 |
| Meeting Space & AV | $3,128 |
| Travel Total | $71,166 |
| Hotel Meals | $25,421 |
| Restaurant Meals | $7,790 |
| Stipend Meals | $7,036 |
| Total Meals | $40,247 |
| Disney/Team Activities | $7,203 |
| Swag | $2,182 |
| Speakers & Entertainment | $4,495 |
| Entertainment Total | $13,880 |
| Grand Total | $125,293 |
Feedback from the team
After the trip, we sent out a short survey to see what landed and what didn’t.
A lot of the feedback touched on the same point. People liked finally understanding what other teams actually work on. The department presentations helped connect the dots between roles, projects, and day-to-day decisions. Several people mentioned that it was easier to see how their work fit into the bigger picture once they heard directly from other teams.
The Orlando-specific touches went over well. The Dapper Dans and the magician were a nice break in the middle of long days, and leaning into the location didn’t feel forced. The Disney parks day was a clear favorite.
Food was mentioned more than I expected. The catered meals worked, and people liked having options around Disney Springs. The meal stipends for travel days and the park day made things easier and removed a lot of small friction.
The overall structure of the week mostly worked. Two days of meetings followed by a day at the parks felt like a good balance. The mix of full-group sessions and smaller discussions kept things moving without feeling packed from morning to night.
What we’d change next time
The survey was also useful for spotting where things fell short.
The biggest theme was time. People wanted more space to just talk. Less scheduled activity, and more room for conversations that happen between sessions or over coffee. We packed a lot into the schedule, and in hindsight, it probably could’ve breathed a bit more.
Several people also asked for more time with their own teams. We did some small-group work, but it felt rushed for a few groups. Longer blocks or more sessions would’ve helped.
Lunch came up more than expected. Catering was easy, but it kept everyone in the same room for most of the day. A few people suggested going off-site or having open lunch hours to break things up.
We handled audio and video ourselves, including flying equipment from Bowling Green. It worked, but not perfectly. The projector screen was too small for the room, and some slides were hard to read. A few people suggested printed decks on the tables, which would’ve helped.
Most hotel stays were smooth, but not all of them. A handful of people ran into room issues, which is something we’ll pay closer attention to next time.
What we took away from it
Once we stepped back and looked at the cost alongside the feedback, a few things were clear.
The money is easy to measure, but the impact is a bit more difficult. Spending $125,293 is a real decision, but after meeting in person, people communicated more smoothly once they were back home. Slack conversations felt less tense, and quick questions stayed quick.
Time together compressed a lot of relationship-building. A few days of shared meals, hallway conversations, and unplanned side chats did more than months of scheduled calls. People felt more comfortable with each other, and that showed up in how work got done afterward.
Having everyone in the same room mattered. Hearing the same updates at the same time cut down on confusion later. There were fewer follow-up questions and less secondhand interpretation.
The structure played a role, too. The mix of meetings, smaller group time, and time away from work mostly worked, but it wasn’t perfect. More informal and small-team time would have helped, and that’s something I’ll plan for next time.
Looking ahead
Would I do it again? Yes. The feedback made that decision easy. Orlando raised the bar, and we’ll take what we learned and build on it for 2026.
About the Author
Shawn Rubel is the founder and CEO of Vecteezy. A designer by background, Shawn launched Vecteezy in 2007 as a creative outlet to help fellow designers find high-quality, affordable visual resources. What started as a side project has since grown into a global platform serving millions of users and a four-time Inc. 5000 honoree.
Photo by Songquan Deng