Prompt: Email Marketing – Re-Engagement / Win Back Sequence

Context: I need to create a re-engagement email sequence for [insert company name], targeting subscribers who have not opened or clicked an email in [insert time period, e.g. “90 days” or “six months”]. We have approximately [insert number] lapsed subscribers. These contacts originally signed up for [insert reason, e.g. “a free guide”, “our newsletter”, “a promotional offer”]. Our current send frequency is [insert, e.g. weekly / fortnightly / monthly]. The main products or services we offer are [insert]. We use [insert email platform, e.g. Mailchimp / Klaviyo / Kartra].

Role: Act as an email marketing strategist who specialises in list health and subscriber re-engagement. You understand the psychology of lapsed subscribers — they are not necessarily gone for good, but they need a compelling reason to reconnect. You know how to write sequences that feel like a genuine conversation rather than a desperate attempt to avoid unsubscribes.

Examples: Write in the style of re-engagement emails from [insert 1–2 brands you admire for their email tone, e.g. “Grammarly, Duolingo, or Innocent Drinks”] — brands that use warmth, light humour, and genuine value to bring people back, rather than alarming subject lines or manufactured urgency.

Action: Write a 3-email re-engagement sequence. Email 1 (Day 1): A warm “we have missed you” email that acknowledges the gap, reminds them of the value they originally signed up for, and presents a clear reason to re-engage. Email 2 (Day 7): A value-led email that gives them something genuinely useful — a piece of content, a resource, or a tip — with no hard sell. Email 3 (Day 14): A final check-in that makes clear this is the last attempt, sets out what they will miss if they unsubscribe, and includes a simple one-click option to stay subscribed or update preferences. For each email provide: two subject line options, preview text, and full body copy.

Tone: [Insert your brand tone, e.g. “Friendly and honest. Not needy or desperate. Clear about what is on offer — no manipulation, no fake countdown timers. Human and conversational.”]

Output Format: Present each email as a clearly labelled separate section. Include subject line options, preview text, and body copy. After each email, note the recommended send trigger and any suggested personalisation tokens. At the end, include a note on when to suppress contacts who do not engage with any of the three emails.

Refinement: Each email should have one primary goal — do not combine a re-engagement message with a sales pitch in the same email. Subject lines should be curiosity-driven or value-led, not clickbait. The final email should feel like a respectful farewell if they choose not to re-engage, not a guilt trip. Aim for under 200 words per email to optimise for mobile reading.