ChatGPT Prompts for Writing a Sales Follow-Up Sequence

1. The Structured Sales Follow-Up Sequence Framework

ChatGPT Prompt:

Create a structured four-email sales follow-up sequence for prospects who haven't responded after an initial contact, spacing emails appropriately over two weeks.

Example Sequence:

• Email 1 (Day 1): Reminder & Reinforce Value
• Email 2 (Day 4): Share Helpful Insight or Case Study
• Email 3 (Day 8): Check-In & Ask Simple Question
• Email 4 (Day 12): Last Attempt Email (Polite Close)

2. The First Follow-Up Email (Reminder & Reinforce Value)

ChatGPT Prompt:

Write a polite follow-up email to a prospect who didn’t respond to an initial outreach, briefly reminding them of the value you offer.

Example Email:

Subject: Quick Follow-Up on [Pain Point]

Hi [First Name],

Just following up on my last message. At [Your Company], we help teams like yours overcome [Pain Point] and achieve [Key Benefit].

Would you be open to a brief conversation this week?

Let me know either way!

Best,
[Your Name]

3. The Second Follow-Up Email (Share Insight or Case Study)

ChatGPT Prompt:

Write a follow-up email sharing a relevant insight or case study to a prospect who hasn’t responded yet.

Example Email:

Subject: How [Similar Company] Solved [Pain Point]

Hi [First Name],

I thought you might find this interesting. [Similar Company] recently tackled [Pain Point] using [Your Product], resulting in [Specific Result].

Does this resonate with your current priorities?

Happy to chat if you're interested!

Best,
[Your Name]

4. The Third Follow-Up Email (Check-In & Simple Question)

ChatGPT Prompt:

Write a casual check-in email to a prospect who hasn’t responded, asking a simple question to encourage a reply.

Example Email:

Subject: Quick Check-In

Hi [First Name],

I understand things can get busy. Just wanted to ask: Is solving [Pain Point] still on your radar for this quarter?

Let me know—I appreciate any update!

Best,
[Your Name]

5. The Fourth Follow-Up Email (Last Attempt)

ChatGPT Prompt:

Write a polite last-attempt follow-up email to a prospect who hasn’t responded after multiple tries, offering them a way to opt out gracefully.

Example Email:

Subject: Should I Close Your File?

Hi [First Name],

I’ve reached out a few times and haven't heard back. I don’t want to keep bugging you if this isn’t a priority.

If now isn’t the right time, I totally understand. Just let me know, and I'll close your file.

If things change, feel free to reconnect anytime!

Best,
[Your Name]

6. The Follow-Up After a Product Demo

ChatGPT Prompt:

Write a follow-up email summarizing key points from a recent product demo and asking about next steps.

Example Email:

Subject: Follow-Up from Our Demo

Hi [First Name],

Thanks again for joining the demo yesterday! To recap, we discussed how [Your Product] can help [Company Name] address [Pain Point] and achieve [Benefit].

Do you have any further questions, or should we discuss next steps?

Let me know how you'd like to proceed.

Best,
[Your Name]

7. The Follow-Up After Sending a Proposal

ChatGPT Prompt:

Write a follow-up email checking in after sending a sales proposal, asking if the prospect has any questions or feedback.

Example Email:

Subject: Checking In on the Proposal

Hi [First Name],

Just wanted to check in regarding the proposal I sent on [Date]. Have you had a chance to review it?

I’m here to answer any questions or discuss adjustments as needed.

Looking forward to your feedback!

Best,
[Your Name]

8. The Follow-Up to a "Not Right Now" Response

ChatGPT Prompt:

Write a follow-up email to a prospect who said "not right now," to re-engage them after a few months.

Example Email:

Subject: Checking Back on [Pain Point]

Hi [First Name],

Hope you’ve been doing well! Last time we spoke, you mentioned it wasn’t the right time to discuss [Pain Point].

Has anything changed? We’ve recently helped companies like [Client Name] achieve [Result], and I’d love to explore if we can help you too.

Would you be open to reconnecting?

Best,
[Your Name]

9. The Follow-Up After a Free Trial

ChatGPT Prompt:

Write a follow-up email for prospects who recently completed a free trial, asking for their feedback and discussing next steps.

Example Email:

Subject: How Was Your Free Trial?

Hi [First Name],

Your free trial just ended—how was your experience? Were you able to explore how [Your Product] can help with [Pain Point]?

I'd love to discuss any feedback you have or help with next steps.

Let me know a good time to connect!

Best,
[Your Name]

10. The Follow-Up for Unresponsive Customers at Renewal

ChatGPT Prompt:

Write a follow-up email to a customer who hasn't responded to renewal communications, gently reminding them and offering assistance.

Example Email:

Subject: Your Subscription is Ending Soon

Hi [First Name],

Just a friendly reminder—your [Product/Service] subscription expires on [Date].

Are you planning to renew? If you have any questions or concerns, I’m here to help.

Looking forward to hearing from you!

Best,
[Your Name]

Final Thoughts: How to Write an Effective Sales Follow-Up Sequence

• Stay polite and professional – Always respect the prospect’s time.
• Provide value in each email – Share insights, case studies, or resources.
• Space out your emails appropriately – Avoid overwhelming the prospect.
• Be concise and clear – Keep your messages brief and to the point.
• Give them an easy out – Offer prospects a way to opt out gracefully.

Use these ChatGPT-powered prompts to build follow-up sequences that increase responses, keep prospects engaged, and ultimately close more deals!