ChatGPT Prompts for Sending a Customer Success Check-In Email

A customer success check-in email is more than just a friendly touchpoint—it’s a strategic way to:

• Strengthen relationships by showing customers you care about their success
• Ensure engagement and keep them using your product and seeing value
• Identify and resolve challenges early to prevent churn
• Encourage growth by uncovering upsell or expansion opportunities

With ChatGPT-powered prompts, you can create personalized, value-driven check-in emails that enhance customer satisfaction and long-term retention.

1. The New Customer Check-In Email (Sent 7-10 Days After Onboarding)

This email ensures new customers are on track and engaged early.

ChatGPT Prompt:

Write a friendly check-in email for a new customer, sent 7-10 days after onboarding, to ensure they’re comfortable with [Your Product] and offer support if needed.

Example Email:

Subject: How’s Everything Going with [Your Product]?

Hi [First Name],

I wanted to check in and see how things are going since you started using [Your Product]. Have you had a chance to [Complete Key Action]?

If you have any questions or need help, I’d be happy to send over some quick tips or schedule a call to walk through anything.

Let me know how I can support you—I want to make sure you’re getting the most out of [Your Product]!

Looking forward to hearing your thoughts.

Best,
[Your Name]
Customer Success Manager, [Your Company]

Why This Works:

• Shows proactive support to reduce frustration early on
• Encourages engagement by prompting action
• Keeps it conversational and approachable

2. The 30-Day Progress Check Email (Ensuring Early Success)

At the 30-day mark, customers should be seeing value—this email reinforces their progress and provides next steps.

ChatGPT Prompt:

Write a 30-day check-in email that asks about the customer’s progress, highlights key wins, and offers a call to discuss next steps.

Example Email:

Subject: 30 Days In – How’s [Your Product] Working for You?

Hi [First Name],

It’s been about a month since you started using [Your Product], and I wanted to check in on how things are going.

So far, many of our customers have achieved [Key Benefit] by [Completing Key Action]. Have you noticed any improvements in [Pain Point]?

I’d love to hear about your experience so far. If you’d like, we can set up a quick call to discuss your progress and any questions you have.

Let me know how I can help!

Best,
[Your Name]
Customer Success Manager, [Your Company]

Why This Works:

• Reinforces progress and early wins
• Encourages feedback to keep the conversation active
• Prevents disengagement by offering support

3. The 90-Day Success Review Email (Reinforcing Long-Term Value)

At 90 days, customers should be seeing measurable impact—this email ensures they are.

ChatGPT Prompt:

Write a 90-day check-in email that highlights the customer’s achievements, addresses any concerns, and discusses expansion opportunities.

Example Email:

Subject: 90 Days with [Your Product] – Let’s Check In

Hi [First Name],

Can you believe it’s been 90 days since you started using [Your Product]? I wanted to check in to see how everything is going.

Many of our customers at this stage have seen [Success Metric] and optimized their workflows by [Using Key Feature]. I’d love to hear what’s working well for you and any challenges you’ve encountered.

Would you be open to a quick success review call? We can discuss any optimizations and explore how to maximize your results moving forward.

Let me know what works for you!

Best,
[Your Name]
Customer Success Manager, [Your Company]

Why This Works:

• Encourages reflection on success to reinforce ROI
• Identifies hidden issues before they escalate
• Opens the door for expansion discussions

4. The Inactive Customer Check-In Email (Re-Engaging At-Risk Customers)

If a customer hasn’t been using your product, this email helps bring them back.

ChatGPT Prompt:

Write a re-engagement email for a customer who has stopped using [Your Product], offering support and an easy way to restart.

Example Email:

Subject: We Noticed You Haven’t Logged In – Need Help?

Hi [First Name],

I noticed that you haven’t been using [Your Product] recently, and I wanted to check in to see if there’s anything we can do to help.

Many of our customers see the best results when they [Key Feature or Best Practice]. If you’d like, I can send over some quick tips or set up a call to help you get back on track.

Let me know how I can assist!

Best,
[Your Name]
Customer Success Manager, [Your Company]

Why This Works:

• Gently re-engages the customer without pressure
• Reminds them of key benefits to encourage a return
• Provides a low-friction action step to make restarting easy

5. The Renewal & Upsell Check-In Email (Encouraging Growth)

If a customer is approaching renewal, this email keeps them engaged and opens expansion discussions.

ChatGPT Prompt:

Write a renewal check-in email that reinforces the value of [Your Product] and introduces potential upgrade or expansion opportunities.

Example Email:

Subject: Maximizing Your Success with [Your Product]

Hi [First Name],

You’ve been using [Your Product] for a while now, and I wanted to check in to ensure you’re still getting the most out of it.

Many of our customers at this stage find that upgrading to [Feature/Premium Plan] helps them [Key Benefit]. Would you be open to a quick chat to explore ways to maximize your results?

Either way, I’d love to hear how things are going! Let me know a time that works for you.

Best,
[Your Name]
Customer Success Manager, [Your Company]

Why This Works:

• Reinforces long-term value to support retention
• Introduces upsell naturally without being pushy
• Encourages a conversation to keep engagement high

Final Thoughts: How to Write Customer Success Check-In Emails That Drive Engagement

• Make it personal – Use the customer’s name and reference their specific journey
• Keep it short and clear – No long paragraphs, just a friendly touchpoint
• Provide value – Share insights, tips, or next steps
• Encourage a response – Ask a simple question to start a conversation
• Be proactive – Don’t wait for problems—prevent them before they happen

Use these ChatGPT-powered prompts to create customer success check-in emails that strengthen relationships, improve retention, and drive long-term growth.