Every DMO I talk to has tried it. You open ChatGPT, you ask it something about your destination, and it gives you a smart, confident, well-written answer. And it’s wrong. Or it’s vague. Or it’s the kind of answer you’d never actually put in front of your board.
That’s not a knock on AI. It’s a knock on how we’ve been asking it to work.
Meet Ken Jennings
Ken Jennings is the greatest Jeopardy! champion of all time. 74-game winning streak. Crowned, officially, the Greatest of All Time in a tournament built for exactly that purpose. The man is a walking encyclopedia – history, science, pop culture, geography, all of it, instantly.
Now imagine asking Ken Jennings to run your destination’s next board report. Or which venue can actually handle a 200-team tournament next spring. Or to create a sales strategy with the hottest target organizers. Or to draft new blog posts that fill gaps in your current content. Or to draft your RFP response to an organizer you’ve been courting for a year.
He’s one of the smartest people alive. And he’d have no idea what he was doing.
He doesn’t know your business, he doesn’t know your venues, he doesn’t know your rates. He’s never seen your RFP history, your brand voice, or the three approval stages a proposal has to clear before it goes out the door. He doesn’t have a deep understanding of the industry or the specific event organizers you should target. He’s a brilliant generalist with none of the context or knowledge that makes his intelligence useful.
That’s AI out of the box – using ChatGPT, Claude or Copilot. It’s not that it’s not smart – it is. But being smart and being useful are two different things, and there needs to be a bridge between them.
Now Imagine Ken Jennings Worked Only for You
Here’s the shift: what if that same brilliant mind spent the next year doing nothing but learning your destination? Every venue, every hotel, every rate, every event you’ve ever hosted. Every RFP that’s come through your door, every event organizer in the industry, every blog post on your website and every engagement you’ve had with a visitor. Your brand voice, your reporting format, your board’s priorities, the way your team actually gets things done day to day.
That person would be unstoppable. Not because they got smarter – because they finally have something to be smart about.
That bridge – the thing that takes a brilliant generalist and turns it into a specific expert on your business – is what the AI industry has started calling the harness. It’s the software layer that sits between raw AI and your actual operation: your data, your workflows, your history, feeding directly into the model so every answer comes from what’s actually true about your destination, not a generic best guess.
This is exactly what we built with Compass Advisor – powered by the Playeasy platform and eight years of destination data, event activity, and industry engagement. Advisor already knows your venues, your hotels & rates, your businesses & discounts, your events, your RFP history, your visitor engagement, the entire event and organizer ecosystem, and how they all connect to each other. It’s not guessing. It’s grounded.
The Piece That Was Still Missing
Here’s what we learned as destinations started using Advisor: knowing your data isn’t the same as knowing your process.
Advisor can see everything happening in your destination. But “what does this destination actually want when they say build an economic impact report” is different from destination to destination. What counts as a qualified sales prospect is different. How you structure a presentation, what your quarterly report needs to include, the exact steps your team follows before an RFP goes out – that’s not data sitting in a database. That’s operational process, built up over years, living in your team’s heads or internal documents.
AI Playbooks are how we close that gap.
A Playbook is a repeatable set of instructions that teaches Advisor exactly how your destination does a specific job – and then Advisor does it that way, every time. Not a generic report. Your report, in your format, pulling your real numbers. Not a canned prospecting summary – the exact information your sales team actually needs to move a conversation forward.
You don’t have to be good at AI to use one. You don’t have to know what a prompt is. You pick the job you need done, and Advisor – guided by the Playbook – walks you through it and hands you something you can actually use.
Why This Matters More Than It Sounds Like It Should
The gap between “AI is impressive” and “AI is useful to my business” is the single biggest reason most organizations feel like they’ve tried AI and it didn’t really change anything. It’s not a model problem. It’s a grounding problem.
Ken Jennings doesn’t need to get smarter to become useful to your destination. He needs context, and a way to apply it consistently. That’s now what Advisor and our AI Playbooks give you – not a smarter assistant, but a specific one. One that already knows your business, and knows exactly how you like the work done.
We’re just getting started.
— Sean