Catch expiring Recurly trials and email them before they end

Every weekday morning, spot the trials ending within three days, email each one personally, and post a recap for your sales team.

Agentic Task
RecurlyGmailSlackSalesEmail AutomationDaily Digests
PromptCreate

Every weekday at 7am, run trial conversion outreach off my Recurly billing data.

Start with the Recurly List Subscriptions operation to pull active subscriptions. Do not assume there is a subscription state literally named "in_trial". Instead, read the trial end date field on each subscription and keep only the ones whose trial ends within the next three days.

For each of those subscriptions, use List Account Subscriptions and List Account Invoices on that account to work out which plan they are on and whether they have any paid billing history yet.

Apply these skip rules before contacting anyone. Skip the account if it already has a paid invoice, since that means they have already converted. Skip it if the subscription is canceled or set to cancel at period end. Skip it if this account was already emailed during this same trial period, and to enforce that, keep a running record of who has been contacted keyed by account code plus trial end date, checking it before sending and adding to it after sending.

For each account that survives the skip rules, draft a short, specific email rather than a generic blast. Reference their actual plan name and their actual trial end date, keep it to a few sentences, make it clear what happens when the trial ends, and offer to help. Send it with the Gmail Send a Message operation to the email address on the Recurly account.

Finish by posting a single Slack summary message, not one message per account. List everyone who was contacted along with their plan name and trial end date, note how many were skipped and why, and call out the higher value plans so the sales team knows who is worth a manual follow up. If no trials are ending in the window, still post a short note saying there was nothing to contact today.

Example output

Trial conversion outreach, Tuesday 7:00am Contacted 3 expiring trials: 1. Northwind Design (Pro Monthly) - trial ends Thu Aug 13 2. Bellweather Labs (Team Annual) - trial ends Fri Aug 14 3. Cato Freight (Starter Monthly) - trial ends Fri Aug 14 Skipped 4: 2 already have a paid invoice, 1 canceled, 1 already emailed earlier this trial. Highest value by plan: Bellweather Labs on Team Annual, worth a manual follow up today.

What does this prompt do?

  • Checks your active subscriptions each weekday morning and pulls out the trials that end within the next three days.
  • Looks up each account's plan and billing history so the email can reference their real plan name and trial end date instead of going out as a generic blast.
  • Skips anyone who has already paid, already canceled, or has already been contacted during this same trial.
  • Posts one Slack summary listing who was contacted, the plan they are on, and when their trial ends, so your sales team can follow up manually on the high value ones.

What do I need to use this?

  • A Recurly account with subscriptions and trials you want to track
  • A Gmail account to send the outreach from, such as a shared sales inbox
  • A Slack workspace and a channel where the daily summary should land

How can I customize it?

  • Change the timing, such as running it every day instead of weekdays only, or shifting the 7am send.
  • Widen or narrow the three day warning window to match how long your trials actually run.
  • Adjust the tone and length of the email, or send the summary to a different Slack channel.

FAQs

Will the same customer get emailed twice?
No. Once someone has been contacted about a trial, they are recorded and skipped for the rest of that trial period. If they start a brand new trial later on, they become eligible again.
Does it email people who already paid or already canceled?
No. Anyone with a paid invoice on their account is treated as converted, and canceled subscriptions are left alone. Only genuinely expiring trials get an email.
What happens on a day when no trials are ending?
No emails go out. The Slack summary simply notes that there was nothing to contact that morning, so you still know the check ran.
Can I review the emails before they send?
By default they send automatically. If you would rather approve them first, you can have the workflow post the drafts to Slack and wait for your go ahead instead of sending straight away.
Can it send from a shared team inbox instead of a personal address?
Yes. Connect whichever Gmail account you want the outreach to come from, such as a sales or billing inbox, and replies land there.

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Stop letting trials expire in silence.

Set up trial conversion outreach that knows each customer's plan and deadline, and tells your sales team who to chase.