CHECK CHERRY + AI
Put an AI Advisor
on Your Team
Connect Check Cherry to the AI tools you already use, like ChatGPT and Claude, and get an edge most event pros don't have yet: an assistant that actually knows your business. Ask what needs your attention, where you're leaving money on the table, and what to do next, all in plain English.
Free to start. Works with the AI assistant you already use, and you stay in control of what it can see.
What it's like having an AI on your team
Instead of digging through screens, you just ask. Your assistant can tell you who still owes you, what needs attention this week, and where you could earn more, then draft the follow-ups for you. Under the hood it's simply your AI connected to Check Cherry, securely, and only when you ask.
1. You ask
"If you ran my business, what would you change this week?" Ask in plain English, right inside your AI assistant.
2. It connects securely
The assistant securely looks up just the data you've allowed it to see.
3. You get an answer
A clear answer pulled straight from your account, no clicking through screens to find it.
CONNECT YOUR AI ASSISTANT
Hook it up in about two minutes
Point your AI assistant at one URL. Sign in to Check Cherry once, choose what to share, and you're connected.
Your Check Cherry MCP URL
https://www.checkcherry.com/mcp
The same URL works for every AI assistant below.
Claude
Easiest to set upMost Claude plans support custom connectors.
- Open Claude, then go to Settings → Connectors.
- Click Add custom connector.
- Paste your Check Cherry MCP URL (above) as the remote MCP server URL and save.
- Click Connect, then sign in to Check Cherry and approve the permissions you want to share.
- Ask Claude something about your business. That's it.
ChatGPT
Available on most paid ChatGPT plans, using developer mode on the web.
- In ChatGPT, go to Settings → Apps.
- Click Advanced and turn on Developer mode.
- Add a custom connector using your Check Cherry MCP URL.
- Sign in to Check Cherry, approve what to share, and start asking.
Cursor & other MCP clients
Any tool that speaks the Model Context Protocol can connect.
Add the Check Cherry MCP URL as a remote MCP server in your client's configuration. The sign-in and permission step happens automatically the first time you connect.
Browse MCP-compatible appsYou're in control
- You choose exactly which permissions to grant when you connect.
- The assistant only sees your business, scoped to your account.
- Disconnect any time from your AI tool or your Check Cherry settings.
- It reads your Check Cherry data and won't email clients or charge cards on its own.
PROMPT LIBRARY
Things to ask once you're connected
Less "run me a report," more "be an advisor who already knows my business." Copy any prompt, paste it into your connected assistant, and tweak the bits in brackets.
New to this? Start here
Give me a 5-minute briefing on my business
Review my Check Cherry account and give me a quick briefing on my business: what needs my attention this week, where I might be leaving money on the table, and one thing I should fix in my setup. Keep it short and prioritized.
Which leads should I contact today?
Review my Check Cherry leads and tell me which ones I should contact today and why, starting with the most time-sensitive.
Critique my packages
Review my packages in Check Cherry and critique them from a customer's point of view. What's clear, what's confusing, and what's missing?
What needs my attention this week?
Review my Check Cherry bookings and tell me which ones need my attention this week, and what to do about each.
Which events are missing information?
Check my upcoming events in Check Cherry and tell me which ones are missing important details like location, timeline, or contact info.
Be my business coach
Act as my business coach. Review my recent Check Cherry activity (the last 60 days) and tell me the top 3 to 5 things I should focus on this month.
I'm new at this — how am I doing?
I'm fairly new to running this kind of business. Review my recent Check Cherry activity and my packages, and tell me, kindly and honestly, what I'm doing well and what I should work on.
How do I get started in Check Cherry?
Search Check Cherry's help center and give me a simple, step-by-step plan for setting up my account from scratch.
Or browse the full library by category.
Give me a 5-minute briefing on my business
Review my Check Cherry account and give me a quick briefing on my business: what needs my attention this week, where I might be leaving money on the table, and one thing I should fix in my setup. Keep it short and prioritized.
Which leads should I contact today?
Review my Check Cherry leads and tell me which ones I should contact today and why, starting with the most time-sensitive.
Draft follow-ups for my best leads
Look at my most promising open leads in Check Cherry and draft a friendly, no-pressure follow-up message for each one. I'll review before sending.
Find cold leads worth another try
Find leads in Check Cherry that went quiet a while ago but might still book, and suggest how I could re-approach each one.
Summarize a lead and my next step
Summarize lead [name] from Check Cherry: what they want, their event date, and the single best next step I should take.
What can I learn from leads that didn't book?
Look at recent leads in Check Cherry that didn't end up booking and tell me if you notice anything I could do differently next time.
Where could I find more revenue?
Review my upcoming bookings and add-ons in Check Cherry and suggest a few concrete ways I could bring in more revenue this month.
Which add-ons should I promote more?
Look at my add-ons and my recent bookings in Check Cherry and tell me which add-ons I should promote more often, and to which kinds of clients.
Who still owes me money?
Review my upcoming and recent events in Check Cherry and list which ones still have a balance due, how much is owed, and who I should follow up with.
Help me upsell my next events
Look at my upcoming events in Check Cherry and suggest one add-on or upgrade I could offer each client that fits what they already booked.
Critique my packages
Review my packages in Check Cherry and critique them from a customer's point of view. What's clear, what's confusing, and what's missing?
Do my packages follow good/better/best?
Look at my packages and prices in Check Cherry and tell me whether they follow a clear good/better/best structure, and how I could improve it.
Rewrite my package descriptions
Review my package descriptions in Check Cherry and rewrite them to be clearer and more compelling, without overpromising.
Where are the gaps in my pricing?
Look at my package prices in Check Cherry and tell me where the gaps in my pricing ladder are, relative to each other, and what I might add to fill them.
What will customers ask before booking?
Based on my packages and descriptions in Check Cherry, what questions will customers likely have before booking, and what should I add to answer them up front?
What needs my attention this week?
Review my Check Cherry bookings and tell me which ones need my attention this week, and what to do about each.
Which events are missing information?
Check my upcoming events in Check Cherry and tell me which ones are missing important details like location, timeline, or contact info.
What's on my calendar this week?
Review my Check Cherry calendar and tell me what events and appointments I have this week, plus anything I should prepare for each.
Build my prep plan
Look at my events over the next two weeks in Check Cherry and build me a simple preparation checklist for each one.
Get me ready for this weekend
Review my Check Cherry calendar and tell me everything I need to know and do to be ready for this weekend's events.
Am I free on a date?
Check my Check Cherry availability for [date] and tell me what's open.
Find time for a consultation
Find open appointment slots in Check Cherry for a 30-minute consultation next week.
Be my business coach
Act as my business coach. Review my recent Check Cherry activity (the last 60 days) and tell me the top 3 to 5 things I should focus on this month.
I'm new at this — how am I doing?
I'm fairly new to running this kind of business. Review my recent Check Cherry activity and my packages, and tell me, kindly and honestly, what I'm doing well and what I should work on.
If you ran my business...
If you were running my business, review my recent Check Cherry activity and tell me the first thing you'd fix this week, and why.
What patterns do you notice?
Look across my leads and bookings from the last 90 days, plus my packages, in Check Cherry, and tell me what patterns or trends you notice that I might be missing.
How do I get started in Check Cherry?
Search Check Cherry's help center and give me a simple, step-by-step plan for setting up my account from scratch.
How do I set up online booking?
Using Check Cherry's help articles, walk me through setting up online booking step by step.
How do payment plans work?
Search Check Cherry's support articles and explain how payment plans work and how I set one up.
How do I send a contract?
Using Check Cherry's help center, show me how to send a contract for signature, step by step.
How do I set up automated messages?
Using Check Cherry's help center, explain how to set up automated messages, with the exact steps.
I'm stuck — find the right help article
I'm trying to [do something] in Check Cherry. Search the help center, point me to the right article, and summarize the steps for me.
No prompts match your search. Try a different word or category.
Tips for better results
Treat your assistant like a sharp new team member who just needs a little direction.
Be specific
Name the client, the date range, or the package. The more precise you are, the better the answer.
Ask follow-ups
You're having a conversation. Drill in with "now just the unpaid ones" or "sort by date."
Ask it to draft
Have it write the follow-up email or the recap. You review and send, so you stay in control.
Start read-only
Get comfortable asking questions first. Grant more access later if you want it to make changes.
Frequently asked questions
What is an MCP server, really?
MCP stands for Model Context Protocol. It's an open standard that lets AI assistants connect to outside tools safely. The Check Cherry MCP server is what lets an assistant like ChatGPT or Claude look up your bookings, leads, and payments when you ask, without you copying and pasting anything.
Is it safe? What can the AI see?
You're in control. When you connect, you sign in to Check Cherry and choose exactly which permissions to grant. The assistant only sees your own business data, and you can disconnect at any time from your AI tool or your Check Cherry settings.
Can it make changes, or just answer questions?
Most people start by asking questions and having it draft emails or recaps, which you review and send yourself. It can do more if you grant those permissions, but it won't email clients or charge cards on its own.
Which AI assistants work with it?
Any assistant that supports the Model Context Protocol, including Claude, ChatGPT, and Cursor. You connect them all with the same Check Cherry MCP URL.
Does it cost extra?
No. Connecting an AI assistant is included with every Check Cherry account at no extra cost, on every plan. You just connect the AI tool you already use.
Do I need to be technical to set it up?
No. If you can paste a URL into your AI assistant's settings, you can connect Check Cherry. The whole thing takes a couple of minutes, and the steps are above.
Get the edge most event pros don't have yet
Start a free trial, connect the AI you already use, and run a sharper business from day one. No more digging through screens for answers you can just ask for.