iBooked Online

We are living through a strange moment. Speed has become a virtue all on its own. Everything has to be faster, cheaper, more automated, more efficient. And in the rush to optimise everything, we have quietly stopped asking whether the thing we are optimising actually matters.

That tension is everywhere in our industry right now. Operators are pouring time into revenue management, dynamic pricing, OTA visibility, AI listings, direct booking funnels. All of it important. But while everyone is fighting for the booking, the part that comes after the booking, the actual stay, is often held together with manual workarounds and the hope that nothing breaks.

This week I sat down with Corrine Harris, General Manager at Operto, to talk about exactly that. The middle of the guest journey. The part that decides whether someone leaves a review, comes back, or quietly never books with you again.

Corrine is the real deal. She has been at Operto for five years, but the more useful credential is the years before that running her own property management business. She has lived the 4am phone calls, the manual chaos, the cleaner who didn’t show. So when she talks about what is broken in guest experience, it is not theory.

A few things from the conversation that really stuck with me:

The middle of the journey is where loyalty is built or lost. You can win the booking with perfect pricing and a beautiful listing, but if the guest can’t find the door code, can’t figure out the coffee machine, and waits four hours for a reply, none of that front-end work matters. The next booking comes from the experience, not the listing.

Getting into the property is the unglamorous problem that wrecks the most stays. Not flashy, not exciting, but Corrine reckons it is still the single biggest source of pain in short-term rentals. A guest who is fumbling under a log for a lockbox has already started their holiday wrong, and that first impression is almost impossible to claw back.

Guest expectations have quietly caught up with hotels. The old idea that vacation rentals get a free pass because “you’re staying in someone’s home” is gone. Guests now walk in expecting perfectly pressed sheets and instant responses, and a lot of operators haven’t adjusted.

AI is not replacing the team, it is unlocking the team. We landed in the same place on this. The fear that AI would gut hospitality jobs has not played out. What we are both seeing is the opposite. The right tools mean a new team member can be productive in days instead of months, which means you can hire more people and do more, not less.

The biggest takeaway for me was Corrine’s advice on not chasing every shiny new tool. The industry right now is flooded with AI products, half of them won’t be around next year, and every week there’s a pitch that “changes everything”. Her line was simple. Pick one or two things that will actually move the needle, do them properly, and ignore the noise. That advice is worth the episode on its own.

What you’ll learn in this episode:

🚪 Why getting the guest into the property is the unglamorous problem that wrecks the most stays

📱 How to automate guest communication without losing the human touch

🧹 The cleaning, maintenance and preventative work most operators forget to systemise

🛎️ Why guest expectations have caught up with hotels, and what that means for your operation

🤖 How to think about AI and new tools without wasting months on the wrong one

Corrine is the General Manager at Operto, based in Calgary, and brings 15+ years of leadership across both hospitality and SaaS to the role. Before stepping into the technology side of the industry, she ran her own property management business, which is the experience that makes her thinking actually useful. She has lived the 4am phone calls and the manual chaos, and now spends her time helping operators around the world translate that complexity into systems that work. Operto integrates with 70+ PMS platforms and handles the entire window from booking to post-checkout. Codes, guidebooks, guest communications, scheduling, the lot.

The reason this one matters: most operators are pouring effort into the top of the funnel and leaving the middle on autopilot. Corrine’s point is that the middle is where you earn the next booking. If your guest experience between booking and checkout is held together with manual workarounds, you are leaking the things that compound. Reviews, returns, word of mouth.

If you have been getting comfortable with a clunky middle-of-the-journey setup, this episode is a useful reset.

📺Watch the episode here