ChatGPT Prompts for Automating Sales Outreach

Automating your sales outreach can help you:

• Save time and effort by automating routine tasks
• Increase efficiency with consistent follow-ups
• Scale outreach to reach more prospects
• Personalize at scale using relevant data
• Track results and optimize based on performance

With ChatGPT-powered prompts, you can create automated outreach sequences that still feel human, personalized, and highly effective.

1. The Automated Cold Email Sequence

ChatGPT Prompt:

Create a three-email cold outreach sequence to prospects in [Industry], highlighting key benefits of [Your Product] and including a follow-up structure.

Example Sequence:

Email 1 (Day 1): Subject: Improving [Key Pain Point] at [Company Name]

Hi [First Name],

I noticed that [Company Name] focuses on [Industry Focus]. At [Your Company], we help companies like yours solve [Pain Point] by [Briefly How Your Product Helps].

Companies like [Customer Name] saw [Specific Result] after using our solution. Would you be open to a quick 15-minute chat this week?

Best,
[Your Name]

Email 2 (Day 4): Subject: Quick Follow-Up on [Pain Point]

Hi [First Name],

Just following up on my last email about [Pain Point]. I understand you’re busy, but I believe our solution could help [Company Name] achieve [Key Benefit].

Are you available for a brief call next week? If not, no worries—let me know either way!

Best,
[Your Name]

Email 3 (Day 7): Subject: Closing the Loop—Let me know!

Hi [First Name],

I haven’t heard back, so I’ll assume it’s not the right time. If [Pain Point] becomes a priority, please keep us in mind—we’d love to help.

Feel free to reach out anytime.

Best,
[Your Name]

2. The Automated LinkedIn Outreach Message

ChatGPT Prompt:

Write a LinkedIn connection request message followed by a brief follow-up message that can be sent automatically to prospects in [Industry].

Example Messages:

Connection Request: Hi [First Name],

I came across your profile and saw your work in [Industry Focus]. I’d love to connect and share insights—I work with companies tackling similar challenges.

Best,
[Your Name]

Follow-Up Message (2 days after connecting): Hi [First Name],

Thanks for connecting! We help [Industry] companies with [Specific Pain Point]. Would you be open to a quick exchange of ideas? No pressure—just a conversation.

Let me know!

Best,
[Your Name]

3. The Automated Post-Download Follow-Up Email

ChatGPT Prompt:

Write an automated follow-up email to send after a prospect downloads a resource (ebook, report) from your website.

Example Email:

Subject: Thanks for Downloading [Resource Name]!

Hi [First Name],

Thanks for downloading [Resource Name]! I hope it’s helpful as you work on [Relevant Goal].

If you have any questions or want to learn how [Your Product] can help with [Key Benefit], feel free to reply here or schedule a quick call.

Best,
[Your Name]

4. The Automated "Re-Engage Cold Leads" Sequence

ChatGPT Prompt:

Write a two-email sequence to re-engage leads who stopped responding after initial interest.

Example Sequence:

Email 1 (Day 1): Subject: Still Interested in Solving [Pain Point]?

Hi [First Name],

We spoke earlier about [Pain Point], and I wanted to check in again. Since we last connected, we’ve helped companies like [Client Name] achieve [Key Result].

Would you be open to reconnecting briefly?

Best,
[Your Name]

Email 2 (Day 4): Subject: Last Check-In—Let Me Know!

Hi [First Name],

I don’t want to bother you if this isn’t a priority anymore. I’ll assume it’s not the right timing if I don’t hear back.

If things change, you know where to find me!

Best,
[Your Name]

5. The Automated "Thank You & Next Steps" Email After a Demo

ChatGPT Prompt:

Write an automated thank-you email to send after a product demo, summarizing key points and confirming next steps.

Example Email:

Subject: Thanks for Your Time Today!

Hi [First Name],

Thanks for joining the demo today—I hope it was valuable! We discussed how [Your Product] can help [Company Name] address [Pain Point].

As a next step, I’ll send a detailed proposal by [Date]. Does that timeline work for you?

Feel free to reach out with any questions.

Best,
[Your Name]

6. The Automated Upsell/Cross-Sell Sequence to Existing Customers

ChatGPT Prompt:

Write a two-email automated sequence for existing customers to introduce an upsell or cross-sell opportunity.

Example Sequence:

Email 1 (Day 1): Subject: Get More Out of [Your Product]

Hi [First Name],

Thanks for being a valued customer! I wanted to let you know about [Upsell Product/Feature], which helps customers like you achieve [Additional Benefit].

Would you like a quick walkthrough?

Best,
[Your Name]

Email 2 (Day 5): Subject: Unlock Even More Value with [Feature]

Hi [First Name],

Just following up on my last email—would you like to learn more about how [Upsell Product/Feature] can benefit your team?

Let me know what you think!

Best,
[Your Name]

7. The Automated Event Invitation Sequence

ChatGPT Prompt:

Write a two-email sequence inviting prospects to an upcoming webinar or event, with reminders.

Example Sequence:

Email 1 (Day 1): Subject: Invitation: Join Our Webinar on [Topic]

Hi [First Name],

We’re hosting a webinar on [Date] about [Topic]. You’ll learn [Key Takeaways].

Register here: [Link]

Hope to see you there!

Best,
[Your Name]

Email 2 (Day before event): Subject: Reminder: Webinar on [Topic] Tomorrow!

Hi [First Name],

Quick reminder that our webinar on [Topic] is happening tomorrow! Register here if you haven’t yet: [Link]

Looking forward to it!

Best,
[Your Name]

8. The Automated Customer Testimonial Request Email

ChatGPT Prompt:

Write an automated email to request a customer testimonial after a successful onboarding period.

Example Email:

Subject: We’d Love Your Feedback!

Hi [First Name],

We hope your experience with [Your Product] is going great! If you have a moment, could you share a quick testimonial about your experience?

Just reply to this email with a sentence or two. We’d really appreciate it!

Thanks again!

Best,
[Your Name]

Final Thoughts: How to Automate Sales Outreach Effectively

• Personalize at scale – Use variables like [First Name] and [Company Name]
• Keep it short & relevant – Clear, concise emails get better responses
• Add value – Provide resources, insights, or helpful info
• Time it right – Space out emails appropriately
• Always include a CTA – Guide prospects toward the next step

Use these ChatGPT-powered prompts to set up automated sales outreach that’s efficient, effective, and feels human!