For Remote-First Companies, the Annual Offsite Isn't a Perk

01 /The Concept

Corporate retreats are a logistics nightmare that falls on whoever got voluntold to plan it – and for remote-first companies, they're no longer optional. TeamOut figured out it was solving the wrong version of that problem before it found the right one.

Through the platform, companies can source all the logistics they need – travel for participants, accommodation, meals, and activities for downtime between corporate workshops and sessions.

TeamOut is a combination of marketplace, planning tool, and concierge service. At its best, a company tells the startup how many people are attending, what they want, and what the budget is – and TeamOut delivers a selection of ready-to-book options. Pick one, and the full operational and logistics package comes with it, turnkey.

The accommodation catalog includes hotels and vacation homes selected specifically for proximity to airports – so getting there and back is straightforward.

Because TeamOut sends clients to the same properties regularly, bookings through the platform typically come with discounts of up to 30%.

TeamOut went through Y Combinator in the winter of 2021 at the idea stage. Less than two years in, it had already organized more than 300 retreats for clients including Accenture, Netflix, and L'Oréal.

Total funding stands at $3.2M, with the most recent round of $2.2M closing in the spring of 2022.

In December of last year, however, TeamOut pivoted its model – while continuing to operate in the retreats space. (The date isn't a typo: the startup is French, which is why the date format in their blog is day/month/year)

02 /Why It Matters

First, why does this market matter? Here are the numbers, drawn from a competitor's research:

- 81% of companies surveyed operate fully remotely.

- 43% of them organized two or more offsites in a single year.

- 81% of companies that held retreats brought more than 75% of their staff.

- 81% of those retreats lasted three or more days, with three days being the most common length.

- The average cost per retreat was $220,000; 19% of companies spent more than $500,000 per event.

- Average per-person budget was $2,100, with $300–400 going just to one night of accommodation.

- Companies spent an average of four months planning a single event; 31% spent six months or more.

By 2025, an estimated 36.2 million Americans will be working remotely – a dramatic increase from the 26% working fully remotely in 2022. HubSpot even ran a blog post asking whether corporate retreats are becoming an essential part of the workday.

The broader corporate events market will reach $510.9B in the US by 2030, and offsites are already a meaningful share of that – one that's growing as remote work expands.

Unsurprisingly, the space has attracted a wave of startups: Bizly ([reviewed here](/review/nuzhen-uber-dlja-vstrech)), Flok ([covered previously](/review/flok)), Moniker, Retreat Venues, Troop, NextRetreat, Retreat, and others.

The real question is how to carve out a position inside this trend. That's exactly what TeamOut's recent pivot was designed to answer.

For fully remote companies, offsites aren't optional – they're operational. As one of TeamOut's Y Combinator peers put it: "When you don't share an office, trust among colleagues gradually erodes. If you don't address that, it becomes a problem. So we have to regularly refresh the connection – even if it's just dinner together or a weekend away."

For large in-person companies, retreats are still mostly an optional perk. And in the short run, chasing big in-person companies means chasing bigger budgets.

Despite that short-term appeal, TeamOut chose to focus on the new generation of remote-first companies – where the "necessity" dynamic produces more consistent, recurring demand.

The catch: TeamOut had previously only worked with groups of 20 or more, because a single event that size generated enough revenue to sustain the business for a month. Classic budget-chasing.

The problem was they couldn't reliably land a client that size every month. Not least because as the travel market recovered post-pandemic, hotel prices climbed again – making events for 20 to 100 people unaffordable for many companies.

One day, the founders had a different idea: instead of working exclusively with large groups, work exclusively with small ones.

That required a complete catalog overhaul. Out went large traditional hotels and apart-hotels. In came spacious houses and vacation homes averaging around 10 bedrooms – still near airports, and still offering catering.

The founders pulled it off in three weeks, assembling a new catalog of 100+ venues.

In the very first week after launch, TeamOut signed contracts with three companies – including Netflix. They'd stumbled onto unmet demand.

It turned out that large companies also wanted to send small, focused teams on short retreats – to energize a specific group working on a tight problem, without the months of planning and heavy spend that a full-company offsite requires.

Small, more frequent retreats mean a company will run them more often than the one or two large annual events. TeamOut's model shifts from earning more per event to earning on more events.

There's a retention dynamic at work too. Big events mean big budgets and long planning cycles – companies shop around carefully every time. Small events mean small budgets and fast turnaround – companies prefer a trusted vendor they don't have to re-evaluate. Pull off a few successful small retreats for a company and there's a good chance the next ones flow in automatically.

The result of the pivot: a new offering for groups of 1 to 20 people, replacing the previous "20+ only" model.

03 /Opportunities

Segmentation and focus are the most important decisions any startup makes, in any space. Even when you've identified a growing trend, there's no point grabbing at everything – you end up spreading so thin that you can't get traction anywhere, while burning out trying.

The key to segmentation is defining a niche that demands genuinely different operating processes – not just a different label. You want to be sharp in your niche and structurally unable to compete in others. Your competitors in other niches, by the same logic, can't efficiently compete in yours.

Of course, you won't be able to serve other niches yourself. But that's fine – the point is to dominate the one you chose.

Organizing retreats for groups of five is operationally nothing like organizing them for groups of a hundred. Vendors built for large groups will price small groups out of the market – if they even take the booking. A vendor built around small groups can't handle a large-scale event, in terms of experience, inventory, or service quality.

Too many founders prove their "positioning" with words: "we do X." The more honest test is the opposite: "we don't do Y." That requires real sacrifice.

The general takeaway is to pressure-test your startup – whatever the space – for genuine positioning. Being explicit about what you're not doing is the more honest test of focus than describing what you are. The right question isn't "what's our niche" but "what processes does our niche require that would make us structurally ineffective at serving any other niche?" That's the answer that tells you whether you have a real position or just a label.

As for the specific opportunity: corporate retreat planning for remote-first companies is a real and growing market that's still in its early phase.

Yes, there are already many players. But that's the best evidence of the market's size and legitimacy – a crowded market only stays crowded if there's enough revenue to sustain the players.

There's room to enter with different products, different audiences, and different positioning. TeamOut's new model is one interesting approach – all the more credible because it came from hard-won operational experience, not theory.