Why booking a team offsite is still a nightmare in 2025 – and the massive opportunity this represents.
If you’ve ever tried to book a corporate offsite or team retreat, you know it’s nothing like booking a simple flight or hotel for one person.
Let’s say your company’s 50-person sales team wants to gather next quarter. You’re excited about the event. It might be one of the few times per year that the whole function gets together.
But then the reality hits: someone has to plan it.
Suddenly, what should be a fun team experience turns into a part-time job of hunting for hotels, juggling email quotes, and playing phone tag with sales managers. And that’s before managing the dozens of vendors that will come with such a high investment.
As a founder who’s felt this pain and is building a company to help make it easier for our customers, I’ll say it plainly:
Booking hotels for corporate groups is a sh*t show.
And yet, it’s more important, and more common, than ever.
In this post, we’ll explore:
Spoiler: this market is huge, growing, and has a ton of issues.
Remote and hybrid work have reshaped how companies build culture. Without a physical office, in-person gatherings are how teams:
And so much more…
According to Gallup, 50% of companies are still hybrid and 25% are remote. That means over 75% of U.S. workers are in hybrid or remote roles.
With such distributed teams, intentional in-person time is more critical than ever.
These gatherings aren’t just about culture — they’re strategic.
More and more companies are following suit.
Modern companies often invest in hubs for their in-person teams in various cities and group travel in the form of on-sites, off-sites, and retreats.
First, let’s grasp how big corporate group travel really is.
We’re talking about team offsites, company retreats, sales kickoffs, internal conferences. All the trips where multiple employees converge for a shared purpose.
Group travel isn’t discretionary or wasteful spend. It’s becoming core to how distributed companies operate.
There’s plenty of data to back that up.
Strong relationships = more cohesive and productive teams.
So if group travel is so important…why is booking it still such a pain?
It boils down to this: booking for one and booking for 20+ are completely different animals. But the industry treats them almost the same — until it breaks.
Here’s the difference:
Individual travel (aka transient travel)
Group travel
It’s like booking a flight where you email Delta and hope they reply next week with a quote. Sounds ridiculous, but that’s still the norm for group travel.
Why it’s so bad
Even once you get responses, you're juggling
Don’t forget the internal coordination: taking all those options to your team’s leadership (“Here are three venue options – which do we pick?”), managing attendee info, special requests, and eventually dealing with contracts and deposits.
It’s a project-manager’s Super Bowl. No wonder many HR or operations folks tasked with offsites say it’s one of the worst parts of their job.
We work with People Ops managers who budget dozens of hours to plan a single offsite.
One 66-person retreat we supported had previously taken their team 70+ hours to coordinate. That’s nearly two full workweeks — time pulled away from hiring, onboarding, and everything else on their plate.
Here’s what they were dealing with:
And they almost overpaid.
You can read more about it on the Marco blog here.
Group travel today is fragmented, opaque, and painfully manual. It’s the last corner of corporate travel that still operates like it's 1999.
Marco is solving this problem with Instant Offsites — where teams can explore, compare, and book hotels for groups faster, easier, and more affordably than ever.
We're launching out of beta in June, but want to see a sneak peek?
Next, I’ll dive into the current landscape: What solutions have cropped up? How are teams booking offsites today, and with what mashup of tools? Why do we think that the problem is still largely unsolved?