Write me an upsell email that feels like a useful nudge, not a thirsty sales push.
WHO I'M EMAILING: {customer_segment + their_existing_plan}
WHAT I'M UPSELLING TO: {higher_plan / annual / add-on / additional_seats / new_product}
WHY IT WOULD HELP THEM (real reason, not 'unlock more features'): {your_honest_case}
WHAT IN THEIR USAGE tells me they're a good candidate: {behavioral_signal — hit_limit_3x_this_month / 80%_seat_utilization / etc.}
PRICING DELTA: {current vs upgrade}
WHAT 'NO' WILL COST ME if they don't upgrade: {nothing / mild_churn_risk / they_outgrow_us}
SENDING FROM: {founder / account_manager / generic_sales_alias}
THEIR TENURE: {months_or_years}
THEIR RECENT ACTIVITY mood: {happy_promoter / quietly_using / lukewarm}
DRAFT:
1. **Subject line** — 5-7 words, no 'unlock', no '!', no 'last chance'.
2. **Opener** — name a SPECIFIC thing they did recently that triggered this email. Proves you're paying attention.
3. **The 'because' bridge** — why what they're doing makes the upgrade specifically useful (not 'because we have a Pro plan').
4. **The offer** — clear, simple, no maze of feature tables.
5. **One sentence on the cost** — transparent, not buried.
6. **One sentence on the alternative** — what happens if they stay on current plan (nothing dramatic — honest).
7. **Soft CTA** — 'happy to chat' or 'reply if you want to walk through it'. No 'BOOK A DEMO NOW.'
8. **An out** — they can ignore the email without feeling pressured.
5 sentences max in the body. Short emails feel respectful.0 copies·0 saves·2 views
238 words·1,524 chars
Sample output
Who: mid-market customer, 60 seats currently used out of 50 licensed (over their license cap). Upselling: 75-seat plan. Why helpful: they're getting blocked when 11+ users try to log in simultaneously. Behavioral signal: 60-seat MAU on a 50-seat plan for 4 months running. Pricing delta: $400/mo more. What no will cost: their power users hit error messages and create tickets. Quietly using, 18 months tenure, sending from account manager.
Subject: Heads-up on your seat usage
Hi [Name],
Noticed your monthly active user count has been at 60 for the last 4 months, while you're licensed for 50 — which means your team is occasionally hitting our session limit at peak times (we've seen ~22 instances of this last month).
The simplest fix is bumping you to our 75-seat plan, which would clear the headroom and lower the support ticket load on your side. It's $400/month more than what you're paying now.
If you'd rather stay on 50 seats, no problem — it just means a handful of your users will continue to see the session-limit message at peak.
Want me to walk through it on a call, or would you rather I send a quick comparison doc?
— [Account Manager Name]
Why this works:
Parameters
Text generation parameters
FAQ
Send upsell emails on Tuesday or Wednesday morning. Friday-afternoon upsells get archived. Monday-morning upsells get lost in the inbox flood. The prompt targets Claude Sonnet and lives in the Marketing & Sales category on mycopyprompt.
This prompt is written for Claude Sonnet. It's a text/chat prompt — paste it into Claude Sonnet (or compatible LLMs like Claude or GPT-4) to get the expected output.
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