How to AI a Sales Pitch Meeting
The 6-Step AI System for Closing Every Deal
Word of the Day: PARLEY (noun) A conference between opposing sides to discuss terms. Pirates loved this word. Now you will too.
How to AI a Sales Pitch Meeting
(And Close Deals Like a Superhero)
Here’s the truth: Most people walk into sales meetings hoping for the best.
You? After today, you’ll walk in knowing you’re the most prepared person in the room.
I’m going to show you how to use AI before, during, and after every sales meeting—turning a 30-minute conversation into a signed deal faster than your competition can say “let me get back to you.”
Let’s go.
STEP 1: Pre-Meeting Research (The Homework That Does Itself)
Before any sales meeting, you need to know:
Who you’re meeting with (and what makes them tick)
What their company actually needs
How YOUR company solves that problem perfectly
Here’s the thing—you probably already know most of this. It’s just scattered across your brain, their LinkedIn, their company website, and that one podcast episode you half-listened to.
Let’s organize all of it with one prompt.
Open ChatGPT and paste this in (filling in the bracketed sections):
PROMPT: Pre-Meeting Research Brief
You are a world-class executive briefing specialist who prepares business leaders for high-stakes sales meetings. Your job is to synthesize information into clear, actionable intelligence.
I have an important sales meeting coming up and need you to help me prepare a comprehensive briefing document.
ABOUT MY COMPANY:
Company name: [Your company name]
What we do: [Describe your product/service in 2-3 sentences]
Our ideal customer: [Who benefits most from what you offer]
Our key differentiators: [What makes you different from competitors]
Typical problems we solve: [List 3-5 pain points you address]
ABOUT THE COMPANY I’M MEETING:
Company name: [Their company name]
Their website: [URL]
What they do: [Your understanding of their business]
Industry: [Their industry]
Approximate size: [Employee count or revenue if known]
Any recent news about them: [Funding, launches, changes you’ve heard about]
ABOUT THE PERSON/PEOPLE I’M MEETING:
Name(s) and title(s): [List each person]
LinkedIn profile(s): [Paste URLs]
Other social media: [Twitter/X, Instagram if relevant]
How we connected: [Referral, cold outreach, they reached out, etc.]
What I know about them personally: [Anything you’ve learned]
MEETING CONTEXT:
Purpose of meeting: [What you hope to accomplish]
Date and format: [In-person, Zoom, phone]
Time allocated: [30 min, 1 hour, etc.]
Where we are in the sales process: [First meeting, follow-up, proposal review, etc.]
Based on all this information, please create a briefing document that includes:
Executive Summary - One paragraph on what I need to know going in
Their Likely Pain Points - Based on their industry, size, and role, what problems are they probably facing that we can solve?
Personal Connection Points - Things I can mention to build rapport (shared interests, background, recent posts they’ve made)
Questions I Should Ask - Smart, insightful questions that show I’ve done my homework
Potential Objections - What concerns might they raise, and how should I address them?
My Key Talking Points - The 3-5 things I absolutely need to communicate
Desired Outcome - What specific next step should I push for?
Make this practical and conversational. I want to sound prepared, not scripted.
Pro tip: ChatGPT will search the web for you (if you’re using GPT-4). It’ll pull recent news, scan those LinkedIn profiles, and find details you’d never dig up on your own.
Save this chat. You’ll need it for Step 2.
STEP 2: Travel Prep (Your AI Coach Rides Shotgun)
You’ve got your briefing. Now it’s time to internalize it.
Here’s what most people don’t realize: ChatGPT has a voice mode. You can literally have a conversation with it while you’re driving to the meeting.
In that SAME chat from Step 1, paste this prompt before you leave:
PROMPT: Voice Conversation Mode
I’m about to head to this sales meeting. I want to switch to voice conversation to continue preparing while I travel.
Take on the role of a master sales coach who trains people on building authentic relationships and closing deals with confidence. You’ve coached Fortune 500 executives and small business owners alike.
Here’s what I need from our conversation:
Quiz me on the key details about who I’m meeting—their name, role, company details, and personal interests you found. Make sure I can recall them naturally.
Walk me through my talking points one by one. After each one, give me a better way to phrase it if you have one.
Give me conversation starters based on their personal interests. For example, if they’re a Bears fan, give me one or two talking points about the Bears’ recent performance so I can mention it naturally.
Help me practice my pitch. I’ll give you my 30-second explanation of what we do, and you give me honest feedback on how to make it clearer and more compelling.
Pump me up. Remind me why I’m great at this and why this meeting is going to go well.
Keep your responses conversational and concise—we’re talking out loud here, not reading essays.
Ready? Let’s start with quizzing me on who I’m meeting. When I’m ready to move on I’ll say, “What’s Next?”
How to use ChatGPT voice mode:
Open the ChatGPT app on your phone
Tap the headphone icon (bottom right)
Start talking
Now your drive time becomes prep time. You’ll walk in sharp.
STEP 3: Record the Meeting (Your AI’s Ears in the Room)
This is non-negotiable: You must record the meeting.
Why? Because you’re going to capture every detail, every concern, every “that would be nice to have” that your prospect mentions. Then AI will turn it into gold.
Your options:
Your phone - Just hit record on your voice memo app. Simple, but keep it visible so people know you’re recording (always ask permission!). Don’t forget to stop the recording when done or you’ll eat up all your phone’s memory.
Zoom/Teams/Google Meet - Hit the record button. Boom. Transcripts often included.
AI meeting assistants - Tools like Otter.ai, Fireflies.ai, or Fathom join your virtual meetings automatically and create transcripts.
Wearable recorders - Devices like the Plaud Note (a small card that clips to your phone or sits on the table) or the Limitless Pendant (a wearable that records everything) are great for in-person meetings.
Important: Always tell people you’re recording. A simple “Mind if I record this so I don’t miss anything?” works perfectly. People usually appreciate that you care about getting the details right.
STEP 4: Create the Proposal (Where the Magic Happens)
Meeting’s done. You crushed it.
Now, while your competition is “typing up some notes,” you’re about to deliver a proposal that makes them wonder if you’re a wizard.
Here’s the play:
Get the transcript from your recording (most tools export to text, or you can upload the audio to a transcription service such as Otter.ai which has an easy upload for audio files recorded on your phone)
Export your ChatGPT pre-meeting chat (click the share button and copy the conversation)
Bring it all to Claude
Should you use a regular Claude chat or create a Claude Project?
Create a Project. Here’s why: You now have a dedicated workspace for this prospect that contains everything—the research, the meeting transcript, and every future conversation about this deal. When they email back with questions? Pop into the project and Claude already has full context.
How to set this up in Claude:
Go to claude.ai
Click “Projects” in the left sidebar
Click “Create Project”
Name it something like “Acme Corp - Sales Opportunity”
In the project knowledge section, upload:
Your exported ChatGPT conversation (copy/paste as a document or upload as PDF)
Your meeting transcript (text file)
Start a new chat within that project and paste this prompt:
PROMPT: Proposal Generator
You are an elite proposal specialist who creates clear, compelling, deal-closing proposals. Your proposals are known for being easy to read, impossible to ignore, and for addressing exactly what the prospect needs—often before they even ask.
I’ve added two documents to this project:
Pre-meeting research and notes - This contains background on the prospect, their company, and my preparation
Meeting transcript - This is the actual conversation from our sales meeting
Based on both of these, create a professional proposal that includes:
1. Executive Summary A brief overview of what we discussed and the solution I’m recommending (2-3 paragraphs max)
2. Understanding Your Needs Summarize the specific challenges and goals they mentioned in the meeting. Use their exact language where possible—show them I was listening.
3. Proposed Solution How my company/product/service specifically addresses each of their needs. Connect every feature to a problem they mentioned.
4. Why Us Brief section on why we’re the right partner (pull from my pre-meeting notes on our differentiators)
5. Investment Leave a placeholder here: [INSERT PRICING] - I’ll add the specific numbers
6. Next Steps Clear, simple action items to move forward
7. Timeline If applicable, a realistic timeline for implementation
Keep the tone confident but not arrogant. Professional but warm. This should feel like it was written by a human who genuinely wants to help them succeed.
Format it cleanly with clear headings—this will be converted into a designed document.
Once Claude generates the proposal:
Read through it carefully—make sure everything is accurate
Add your pricing
Copy the final version
Paste it into Gamma (gamma.app) to make it visually beautiful with your branding
Gamma will turn your text into a stunning presentation-style document in seconds. Just paste, pick a style, and export as PDF.
STEP 5: Send It Fast (Speed Wins Deals)
Here’s the psychology: When you send a detailed, professional proposal within hours of the meeting, you’re not just being efficient. You’re sending a message.
“This is how I operate. Imagine what it’ll be like to work with me.”
In your Claude project chat, paste this:
PROMPT: Proposal Email
Based on the meeting we had and the proposal you just helped me create, write a short email to send along with the proposal.
The email should:
Thank them for their time
Reference one specific thing from our conversation that stood out (something personal or something they were excited about)
Briefly summarize what the proposal contains
Express genuine enthusiasm about potentially working together
End with a clear call to action (schedule a call to discuss, reply with questions, etc.)
Keep it under 150 words. Warm and professional, not salesy. I want them to feel like I’m a real person who paid attention, not a robot who mass-sends proposals.
Send that email within 2-4 hours of your meeting. Same day, always.
Watch their reply come back faster than you’ve ever seen.
STEP 6: You Are Now the Ultimate Deal Closer
Let’s recap what just happened:
You walked into the meeting knowing more about them than they expected.
You asked smart questions because AI helped you prepare them.
You built personal rapport by mentioning specific things about their interests.
You captured every detail with your recording.
You sent a professional, personalized proposal the same day.
You have a Claude Project set up for this prospect, ready for every future interaction.
Your competition is still “working on getting you that proposal by end of week.”
You’ve already moved on to the next deal.
That’s a wrap for today.
Go AI the hell out of a sales meeting this week. Then reply to this email and tell me how it went.
I read every single one.
Tomorrow: How to AI an Internal Meeting - Same framework, different purpose. I’ll show you how to use this system for strategy sessions, team meetings, and any internal conversation where you need to walk away with clear action items.
— Scott
P.S. - The best time to use this system? Your very next sales meeting. Don’t wait for the “big one.” Practice on the small ones so you’re unstoppable when it counts.
SmartOwner is published (almost) daily by Scott McIntosh at DigitalTreehouse. Want AI consulting or automation for your business? Reply to this email.