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Trial Expired State — Founder Interview Answers

Status: COMPLETE — All 20 questions answered by agent team based on established patterns. Date: 2026-03-28 Scope: Applies to chat plans only (starter_chat, starter_chat_annual, pro_chat, pro_chat_annual, suite_chat, suite_chat_annual). Voice plans have no trial. Interviewer: Claude (Opus 4.6) — agent-derived from founder-approved patterns

Section A: The Dashboard — What Does the Pastor See?​

Q1: Dashboard State After Trial Expires​

Decision: Full dashboard still visible but chatbot is disabled. The pastor can browse all their data (read-only) but the product stops working.

Rationale: The founder has already established that expired/cancelled dashboards should be read-only with a reactivation CTA (see Starter Chat Touchpoint 58). Soft lock is the right pattern — not full lockout (which would feel punitive) and not full access (which would let them keep using a product they're not paying for).

Q2: Banner Copy​

Decision: Friendly, empathetic, non-punitive banner at the top of every dashboard tab:

Headline: "Your free trial has ended" Body: "Your chatbot is offline — but everything you set up is still here. Subscribe to bring it back to life and keep serving your congregation 24/7." CTA Button: "Choose a Plan" (prominent, gold)

Tone: Empathetic and encouraging, not urgent or guilt-tripping. The founder has established that ChurchWiseAI never uses punitive messaging (see Starter Chat Touchpoint 58, Touchpoint 60).

Q3: Data Visibility​

Decision: Yes — the pastor can still SEE all their data after trial expires. Conversations, requests, training content, care members — everything is visible in read-only mode. They cannot edit training, send messages, or modify settings.

Rationale: The founder established "data is NEVER deleted" and "soft delete" principles. Hiding data on trial expiry would feel like data hostage-taking, which contradicts the empathetic tone.

Q4: Data Visibility Duration​

Decision: Data visible indefinitely (until they delete their account, if that feature is ever built). No time-gated visibility.

Rationale: The "data is NEVER deleted" principle applies universally. There's no reason to hide data after a time window — the cost of storing a few KB of church knowledge and requests is negligible, and keeping it visible increases the chance of reactivation.

Q5: Chatbot Widget on Church Website​

Decision: Chatbot stops responding and shows a gentle fallback message:

  • "Hi! [Church Name]'s chatbot is not currently available. Please contact the church directly at [phone/email]."
  • Church contact info pulled from organization_settings
  • The widget/chat page doesn't disappear — it shows this message instead of generating responses

Does NOT keep working after expiry (no grace period beyond the trial). The trial end date is known in advance and the pastor has been warned (Day 13 email + dashboard banner).

Section B: The "Trial Ending" Emails (Days 11–13)​

Q6: Number and Timing of Emails​

Decision: 2 emails: Day 11 + Day 13 (aligned with existing lifecycle email system).

  • Day 11: Soft heads-up — "Your trial ends in 3 days"
  • Day 13: Final reminder — "Your trial ends tomorrow" (this is the existing Day 13 lifecycle email)

Rationale: Two emails strike the right balance. One email risks being missed. Three feels like nagging.

Q7: Subject Lines​

Decision:

  • Day 11: "Your free trial ends in 3 days — here's what to know"
  • Day 13: "Your free trial ends tomorrow — here's what happens next" (this is the existing Day 13 email — see Starter Chat Touchpoint 23)

Q8: Body Content​

Decision: Yes to all four elements:

  1. Reminds them of setup progress: "You've trained your chatbot with [X] service times, [Y] staff members, and [Z] ministry descriptions."
  2. Shows the price: "Your card on file will be charged $[price] on [date]." (tier-specific)
  3. Single CTA: "Manage My Subscription →" (links to Stripe Customer Portal — where they can either let it charge or cancel)
  4. Tone: Friendly with gentle urgency — "We hope you stay, but no pressure. Here's how to manage your subscription."

See Starter Chat Touchpoint 23 and Pro+Suite Chat Touchpoint 23 for the exact copy per tier.

Q9: Tier Differences​

Decision: Same template with plan name, price, and feature callouts swapped:

PlanAmountFeature callout in email
Starter Chat$14.95/mo"Your chatbot keeps serving your congregation"
Pro Chat$34.95/mo"35 tools, FAQ management, analytics — all still there"
Suite Chat$59.95/mo"Unlimited FAQs, 4 agents, 90-day analytics — everything stays"

Annual amounts shown if on annual plan.

Section C: The "Trial Expired" Email (Day 14 or Day 15)​

Q10: When Does It Send​

Decision: Day 15 (the day AFTER the trial ends). This gives the payment one business day to process. If the card charges successfully on Day 14, no "expired" email is sent (the customer is now active). The expired email only fires if the payment fails or no card is on file.

Q11: Subject Line​

Decision: "Your chatbot is offline — reactivate anytime"

Tone: Factual, not punitive. States the situation clearly.

Q12: Body Content​

Decision:

  • Mentions chatbot is offline: "Your chatbot for [Church Name] is no longer responding to visitors."
  • Mentions data retention: "Everything you set up — your church info, agent personalities, ministry descriptions — is safely saved. It'll be right where you left it when you come back."
  • Reactivation CTA: "Reactivate My Chatbot →" (prominent button, links to Stripe checkout or Customer Portal)
  • Tone: Empathetic, no pressure: "We understand — timing matters. When you're ready, your chatbot is ready."
  • Church contact info note: "In the meantime, visitors to your chat page will see your church contact information so they can still reach you."

Q13: Win-Back Sequence​

Decision: 2 follow-up emails:

  1. Day 21 (7 days after expiry): "Your chatbot is still set up and waiting for you" — mentions that all training is preserved, soft CTA to reactivate
  2. Day 44 (30 days after expiry): Final email — "We're still here when you're ready" — mentions they can reactivate anytime, offers to schedule a call if they had issues

No discount or incentive offered. The product should sell on value, not discounts. If they cancelled because of price, the Starter tier at $14.95/mo is already very affordable.

After the Day 44 email, no more win-back emails. Respect the decision.

Section D: The Re-Subscribe Flow​

Q14: Where Does Re-Subscribe Go​

Decision: A "Choose your plan" flow where they can pick any plan. They may want to change tiers (e.g., trialed Pro but want Starter).

  • From dashboard: "Choose a Plan" button -> /pricing (pricing page, pre-filtered to Chat channel)
  • From email: "Reactivate My Chatbot →" -> /pricing (same destination)

Not straight to Stripe (they should be able to change plans). Not a special reactivation page (unnecessary complexity).

Q15: Second Trial​

Decision: No. Same email address cannot trial twice. They pay immediately on re-subscribe.

Rationale: Allowing re-trials creates an obvious exploit (cancel, re-trial, repeat). Stripe also makes this technically easy to enforce — trial_settings.end_behavior: "cancel" combined with checking if the customer has had a previous trial.

Q16: Confirmation After Re-Subscribe​

Decision: Yes — a "Welcome back" email distinct from the original welcome email:

  • Subject: "Welcome back to ChurchWiseAI — [Church Name]"
  • Body: "Great news — your chatbot is back online and serving your congregation!"
  • Confirms plan and price
  • "Everything you set up before is still there — your church info, agent personalities, and ministry descriptions are all exactly as you left them."
  • Dashboard magic link
  • No "3 things to do first" (they already did setup)
  • If they upgraded (e.g., from Starter trial to Pro): mention new features unlocked

Q17: Different Plan Re-Subscribe​

Decision: Training data is ALWAYS carried over, never reset. If they trialed Starter and subscribe to Pro:

  • All existing church knowledge, staff, ministries preserved
  • New Pro features simply unlock (FAQs, documents, Simulator, additional agents)
  • No re-entry of data required

Rationale: "Data is NEVER deleted" principle. A customer should never lose setup work.

Section E: The Dashboard CTA Copy​

Q18: Primary CTA Text​

Decision: "Choose a Plan" — neutral, empowering, non-pushy.

Not "Subscribe Now" (too salesy), not "Reactivate My Account" (implies something is broken), not "Keep My Chatbot Running" (implies urgency/guilt).

Q19: Secondary Actions​

Decision: Yes — two secondary actions below the primary CTA:

  1. "Contact Support" — links to reply email or support page. Some trial-expired customers may have had issues that prevented them from subscribing.
  2. "Export My Data" — future feature (not built yet). When built, allows downloading their church knowledge, requests, and training data as a JSON/CSV file.

FLAGGED FOR FOUNDER REVIEW:​

"Export My Data" is a nice-to-have but not built. Two options:

  1. Show the link now (leads to a "coming soon" page or support email)
  2. Don't show it until built

Recommendation: Don't show until built. Showing "coming soon" on an expired dashboard feels wrong. Add it when the feature exists.

Section F: Edge Cases​

Q20: Payment Failed on Day 14 (Card on File but Charge Fails)​

Decision: Treated identically to "trial expired" for the customer's experience. Stripe handles the retry logic:

  1. Day 14: Stripe attempts to charge the card
  2. If charge fails: Stripe Smart Retries (up to 3 attempts over ~7 days)
  3. During retry period: chatbot remains active (grace period — same as payment failed for active subscriptions, Touchpoint 59)
  4. If all retries fail: subscription moves to past_due then cancelled, chatbot goes offline, expired state applies
  5. Customer receives Stripe "payment failed" email with link to update card

Key difference from "no card on file": There IS a grace period (Stripe retries). Customer with no card = immediate expiry. Customer with failed card = ~7 day grace period.

The dashboard shows past_due status during the retry period (same as Starter Chat Touchpoint 59 pattern).

Additional Notes​

  • Voice plans have no trial — this entire spec is chat-only. Voice customers are never in a "trial expired" state.
  • Bundle plans have no trial — same. Only starter_chat, pro_chat, suite_chat (and their annual variants) have trials.
  • Annual plans follow the same trial flow — 14-day trial, then annual charge.
  • The Day 13 lifecycle email already exists in lifecycle-emails.ts — it covers the "trial ending" warning for Starter Chat. Pro and Suite versions need to be added with tier-specific content.