If you’re a B2B founder still avoiding sales calls—or improvising your way through them—here’s your fix.
Sales roleplays work. But most are awkward, time-consuming, or fake.
You don’t want to rehearse with someone who already knows your pitch. You need resistance. You need objections. You need pressure.
That’s where ChatGPT comes in.
When prompted correctly, it becomes your toughest prospect, your skeptical VP, or your confused economic buyer—ready to challenge your message in real time.
Here’s how to use ChatGPT to run a roleplay that actually makes you better at selling.
Why AI Roleplay Works (When Done Right)
Traditional sales roleplays fall flat because:
- They’re too friendly
- They don’t reflect your actual buyer
- You already know the outcome
AI solves all of that—if you give it the right inputs.
ChatGPT can:
- Stay in character
- Ask tough, realistic questions
- Push back on vague claims
- Test your value prop under pressure
You’re not scripting. You’re simulating.
The 5-Step Framework for AI Sales Roleplay
1. Define the Buyer Profile
Give ChatGPT the exact persona. Be specific.
“You are a VP of Operations at a $25M B2B SaaS company. You’ve managed two CRM implementations, are skeptical of new software, and hate buzzwords. You’re evaluating tools to improve sales forecasting.”
Now it knows who to be.
2. Set the Context
Tell it why you’re there and what the product does.
“I’m the founder of a RevOps platform that helps mid-market SaaS teams forecast with 30% more accuracy using real-time activity data.”
Now it knows what you’re selling.
3. Add Real Buyer Friction
Don’t ask it to be easy on you. Ask it to be honest.
“Push back on anything unclear, challenge my claims, and make me clarify. Your goal is to uncover risk before buying.”
This is where the pressure builds—and where learning happens.
4. Start the Roleplay
Kick it off like a real call:
“Hi, thanks for making time. Can I ask what prompted your interest in fixing your sales forecast?”
Then respond naturally. Let ChatGPT reply in character. Keep the back-and-forth going.
Every answer you give is a rep.
5. Debrief After Every Session
Prompt:
“Based on that conversation, give me 3 things I did well and 3 I should improve. Focus on clarity, objection handling, and buyer alignment.”
Now you’re not just practicing. You’re coaching yourself—with a feedback loop.
Bonus: Advanced Roleplay Prompts
Want to go deeper? Try:
- “Now play a skeptical CFO who wants ROI in 3 months.”
- “Now act as an internal champion who needs to sell this up.”
- “Now simulate a deal going cold—how should I re-engage?”
These give you exposure to real-world selling dynamics—without risking real deals.
Final Word
Founders don’t need a sales script.
You need reps. You need friction. You need to practice in the dark so you perform in the light.
AI sales roleplay gives you that—on demand, without ego, and without wasting anyone’s time.
So stop guessing how your pitch sounds. Start simulating how it lands.
Then go close the deal.
