Prompt of the week:
Re-engagement is one of the most efficient ways to revitalise your database!
To maximise impact, segmented emails are crucial, driving 30% more opens and 50% more click-throughs than unsegmented emails.
We can ask the assistant to draft a three-part re-engagement email sequence for inactive contacts (e.g., those with no opens or clicks in the past 90 days).
This sequence should be implemented via a HubSpot workflow that uses branching logic.
The workflow's path for a contact is determined by whether they click a confirmation Call-to-Action (CTA) within the sequence.
This is highly valuable because Re-engagement campaigns are a highly effective yet often overlooked strategy for sparking new conversations with inactive contacts.
As a best practice, we would recommend a sequence of at least three emails, spaced 5–7 days apart. With tools like Breeze, generating this full sequence is fast; the copy, which is typically the most time-consuming part, is created in minutes.
Prompt structure
Role: You are a retention-focused email copywriter for [COMPANY NAME], a [BRIEF BUSINESS DESCRIPTION].
Task: Write a 3-email re-engagement sequence for contacts who have not opened or clicked any marketing email in the last [TIMEFRAME, e.g., 90 days].
Brand voice: [DESCRIBE — e.g., "Warm, human, lightly humorous — never corporate or guilt-tripping"].
Sequence structure:
Email 1 (Soft check-in):
- Acknowledge the silence without pressure
- Remind them of the value they originally signed up for
- Include one low-commitment CTA (e.g., "See what's new")
Email 2 (Value-led nudge, sent 5 days later):
- Share a specific piece of high-value content or recent result relevant to [SEGMENT/INDUSTRY]
- Use social proof or a stat to rebuild credibility
- CTA: confirm they'd like to keep receiving emails
Email 3 (Final notice, sent 7 days later):
- Clearly state they will be removed from the mailing list
- Keep it respectful and brief
- Single CTA: "I want to stay subscribed" linking to
[CONFIRMATION PAGE URL]
Constraints:
- Each email should be under 150 words in body copy
- Subject lines should be conversational, not clickbait
- Do NOT use discounts or promotions as incentives
- Include a suggested subject line and preview text for each email
Output: Provide all 3 emails in sequence, clearly labelled.
Think of this prompt as your starter kit, not the finish line. The real power comes when you start building a library of tested prompts that your team can reach for depending on the situation: product launches, seasonal campaigns, event invitations, post-purchase nurtures, and so on.
