Before you read any further, I want you to do one thing.

Open your PMS.

Pull your total guest contacts.

Past guests, inquiry leads, website signups.

Everyone who’s ever raised their hand about your property.

Write down that number.

Now ask yourself: when’s the last time you emailed them?

For most operators, the answer is never.

They have the list. They’ve never touched it.

THE WRONG WAY

Most operators understand the concept.

Some have tried. Fired off a few emails, or brought in a third party to set it up, then let it go quiet when the season picked up.

Most just haven’t started. Email always feels like a project for next month.

There’s a turnover to coordinate.

A maintenance issue.

A review to respond to.

So the list keeps growing.

Email goes to the bottom of the pile.

And the channel stays off.

So what do you do?

THE PLAY

First off, a story: I know an operator in the Rocky Mountains.

She runs a river property she’s owned since 2008.

She’s at 50 to 60% direct bookings without running a single paid ad.

(Not common in her market, where most operators are still taking reservations the old-school way.)

Her husband handles the SEO.

Loyal guests come back every year.

She sells out most seasons on repeat business alone.

(Most operators would consider this a solved problem. She was still leaving money on the table.)

This past season, she priced a stretch of dates too low and sold out two months early.

She had a list of past guests who would have paid more at her real rate.

She had no mechanism to reach them.

Here’s the math most operators haven’t done.

Every other channel you’re using has a cost:

• OTAs take 15 to 25% off the top.
• Paid ads have a cost-per-click.
• An influencer stay has a rate, sometimes a fee.

Email doesn’t cut into your margin at checkout. The guest already chose you once.

Here’s how to turn it on.

The four flows that matter most:

• Welcome. New signups get a short sequence that introduces the property and points to a direct booking link.
• Past-guest reactivation. A single email to guests who stayed 9 to 12 months ago, timed to when they’d naturally start thinking about their next trip.
• Re-engagement. For contacts sitting untouched for 18 months or more. Send them a property update. Something seasonal. Tell them the fall foliage window is open or the elk rut is coming. That’s all it takes.
• Abandoned cart. Guests who started a booking and didn’t finish it.

That last one is where the quickest wins are hiding.

An email service provider can trigger all four automatically. You set it up once and it runs. (Klaviyo is what we use at Oasi. It’s where I’d recommend you start.)

THE PROOF

The six-step direct booking framework at Onera includes email as one of its six levers.

Onera Wimberley hit 85% direct bookings in its first year.

$822,000 in direct revenue in the first five months of operation.

Email didn’t build that alone. But it is load-bearing.

You see, social attracts guests who don’t know you yet. They see a reel, follow the account.

But a follower does not equal a customer.

A well-run email capture changes that. At Onera, guests enter for a chance at a free stay or a discount code. They hand over the address. They start getting the newsletter.

By the time they’re planning that romantic getaway, you’ve been in their inbox a dozen times.

Your past guests are on that list too. They’ve already made the decision once. They know what checkout feels like and what the view looks like from the outdoor tub.

They just need a reason to pick the dates.

THE TAKEAWAY

Your past guests are the warmest audience you have.

They chose you once. They’ll choose you again. But only if you reach them.

Pull the list. Set up the flows.

This is your window before the operators around you figure out the same thing.

Ben