Proptech Growth Strategy Brief Newsletter

Collective Retreats Growth Strategy

Collective Retreats is a outdoor hospitality company that offers high-end glamping experiences near major cities in the U.S.

"Grain of Salt" Warning: I write this newsletter with an outsider's understanding of the business in question. I am likely to make mistakes, leaps of judgement, and assumptions - that's what makes it fun.

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Collective Retreats is a outdoor hospitality company that offers high-end glamping experiences near major cities in the U.S. With lux accommodations, gourmet dining, and exclusive activities, they're looking to take a bite out of the hotel industry by offering differentiated experiences in natural environments, without having to go far from the city.

In June of 2021, Collective Retreats raised $23M in series C funding. "[Collective Retreats] will be the equivalent of a Four Seasons experience, but in nature,", says Jeff Cavins, CEO of one of the funding round's leaders, Outdoorsy.

Strengths & Weaknesses

In most markets, being one of the only players can be a red flag. If there was real opportunity, there should be more competition. But the nascency of this market and the real estate industry's general slowness to jump into new opportunities make Collective Retreat's earliness a strength. This first-mover advantage has led to some great press and decent SEO presence for growing search keywords.

But all is not rosy. They've under invested in media production and web design, which dulls some of the sheen a product as sexy as this should be leaning on. It also feels like there is some confusion around who C.R is for - it feels somewhat like a product looking for a market, suggesting there may be some product management problems here. Lastly, C.R. seems like a product prime for repeat business and referrals, but there doesn't seem to be much infrastructure set up to encourage and take advantage of this yet.

Half of the imagery on Collective Retreat's website feels like it could be stock, and the copy could work a lot harder.

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Opportunities and Threats

Collective Retreat's biggest tailwind is society's post-COVID reemergence. People have been stuck inside for 18 months, and have pockets full of unspent vacation money. Not only that, but the fact that C.R. locations can focus on people in the city they're based in rather than visitors lends C.R. a huge opportunity for repeat business and the optionality to build their own lead generation funnel, rather thansacrificing a big cut to hotel aggregator sites. Tack on a growing discontent around Airbnb's hidden pricing and remote teams hosting more off-sites, and you have an interesting event convergence that could spell success.

The threats facing C.R. aren't much in their control. Glamping has gained steam over the last five years, but that could yet turn out to be a fad. If it's not, they should expect competition from big hotel labels as they aim for a foothold in a new hospitality market.


Given all this, I think the best move for Collective Retreats is to turn itself into a media company, and create a lifestyle brand that brings in passionate, repeat business.

Product & Positioning

Collective Retreats' copy and imagery suggest there's no core reference point guiding decisions on whom their customer is. They should first align on their core target segments, and create detailed user personas to arrange all media around.

Only when personas are completed would I dive into rewriting and reshooting the entire website. This product is aspirational and sexy, and the first step toward creating a story brand around it is to use media to stir desire in their prospects.

Customer Acquisition

The fact that Collective Retreats set up outside major cities will be a huge boon to business for two reasons - repeat business and concentrated buyer market. Providing great experiences will create repeat business, and geo-fencing marketing efforts to a given city will make their marketing budget far more efficient.

Since most people aren't aiming to book a trip right now, I would aim to create segmented email lists within each service city, and use email automations and newsletters to nurture users over time. Eventually, a certain amount of them will pull the trigger and make a booking.

Revenue Optimization

We need to build a system that encourages repeat business. One way to do that is with a subscription. C.R. could make a "Club" of people who pay a subscription fee to have priority booking, discounts, and other perks. Alternatively, repeat bookings can be encouraged by creating accumulating rewards or discounts based on how often someone books.

Assuming repeat visitors are having a great time, we need to empower them to evangelize to their friends and colleagues on your behalf. A double-sided referral program could do that - offer discounts to the new booker and referrer for each new customer they bring.

I'd also consider building out a sales function internally to fill the spaces through the week. There will be lots of corporate meetings and conferences who would love to make use of a unique setting like C.R. provides, providing there's an easy path for them to do so.

That's it for today.  Thanks for reading!

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