Library/AI-Era / Emerging Sales Work/PLG / PQL Sales Motion/Create Trial Check-In Message Sequence for Product Trials
TestedAI-Era / Emerging Sales WorkQuick Win (under 10 min)

Create Trial Check-In Message Sequence for Product Trials

Generate a complete trial check-in sequence from day one through trial end with email and in-app message versions.

About this prompt

This prompt generates trial check-in messages for day one through trial expiry — with subject lines, body copy under 100 words, goals for each touchpoint, alternative messages for low-engagement users, CTAs, and both email and in-app versions. It's for CSMs and AEs managing product trials in PLG motions. Use it when launching any trial period where conversion to paid is the goal.PLG trials succeed or fail based on whether users reach the activation moment — this prompt gives you a structured communication sequence that guides them there rather than hoping they find it on their own. Fill in your product, trial length, the key activation event that signals genuine engagement, and the customer persona, and it generates a calibrated sequence with different messages for engaged vs. low-engagement users at each checkpoint. The day-seven engagement check is the most critical point in most trials — if users aren't active by then, the default path is trial expiry without conversion, and you need the low-engagement variant to re-engage them immediately. The in-app message variants are valuable for product-led motions where email open rates are lower than in-app notification rates. Use this in conjunction with the trial-to-paid conversion plan prompt for a complete PLG conversion playbook.

The prompt

Create trial check-in messages. Context: ● Product: [WHAT YOU SELL] ● Trial length: [DAYS] ● Key activation event: [WHAT SHOWS THEY'RE ENGAGED] ● Customer persona: [WHO'S USING IT] Create check-ins f
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Variables to replace

WHAT YOU SELL|DAYS|WHAT SHOWS THEY'RE ENGAGED|WHO'S USING IT|X-2|X

How to run it

  1. Copy the prompt and paste it into Claude, ChatGPT, Gemini, or Copilot — it's tuned to run in any of them.
  2. Replace the variables — swap each bracketed token for your deal's specifics. The variables list above explains every field.
  3. Make it yours — run it, keep what's strong, and tighten your inputs on the next pass. The prompt improves with your context.

What good output looks like

Make it yours

StageOnboarding/Handoff
SeatCSM, AE
DifficultyIntermediate
Time to valueQuick Win (under 10 min)
Works withAI-Agnostic
CategoryAI-Era / Emerging Sales Work
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