What I learned from an operator managing 200k+ booked nights

Question

Spoke with an operator managing a large STR portfolio (~200k+ booked nights).

They were able to automate ~70–80% of guest messaging.

But the biggest challenge wasn’t the AI.

It was building and maintaining the knowledge base behind it.

Made me realize:

AI works, but only if the operational data is structured properly.

Has anyone here tried automating guest messaging yet?

John Underwood · Answer

I have such a great listing with pictures and description that I rarely get anything I need to respond to.

Andrew Steffens · Answer

I do about 15-20k booked nights per year, in my 10th year.  AI is still new and I have yet to find a useful place for it other than assistant with building lists.  Automations have been around since I started using PMS in maybe 2019 and I have 4 full time reservationists that get me 24/7 coverage.  I think if I went over 100 listings I would need to add more than 1 reservationist on duty during peak hours, and I think that would be where I could leverage AI.  However as of now, the cost does not make sense for me at my size to implement the AI as the automations and having an on duty staff member.

Mike Grudzien · Answer

My 2 cents: I like inserting the human touch when I can.

Izuchukwu Onukwube · Answer

That makes a lot of sense, especially with a team already in place and solid coverage.

Dave Stokley · Answer

Yeah I mean that's how they work. It's not really AI, it's automation. It only knows what you tell it. Just like with VAs, the quality of what you get is directly related to the quality of what you put in.

Dave Stokley · Answer

Yes that's true too, the "AI" part is interpreting what the guest actually needs. But yeah most things that people are calling "AI" right now are really just automation.

Izuchukwu Onukwube · Answer

I actually agree with you.

John Underwood · Answer

We have 2. One I fully manage.

Izuchukwu Onukwube · Answer

That’s a great spot to be in, strong listings definitely reduce a lot of the basic questions.

What I learned from an operator managing 200k+ booked nights

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