Lifecycle Email System

Problem

We have 8 MailerLite automations sending stale/inaccurate info. MailerLite's API cannot create or modify automations programmatically — only the UI can. The founder hates the MailerLite UI. Agents can't maintain these automations. Result: emails rot.

Email Trigger Points

Solution

Replace ALL MailerLite automations with a code-based system:

Resend for sending (already integrated)
Vercel cron for scheduling (already have cron infrastructure)
Supabase table for sent-log / deduplication
React Email for templates (already the pattern for welcome email)
MailerLite stays for newsletter subscriber management and Care broadcasts ONLY

Why Not MailerLite

MailerLite	Our System
Can't create automations via API	100% API-controlled
Can only react to MailerLite data (tags, groups)	Checks Supabase — did they set up FAQs? Service times?
Separate automation per plan	One codebase, plan-aware
Templates in MailerLite UI (founder must edit manually)	React Email in git — agents create/maintain
Stale copy goes unnoticed	Version-controlled, auditable
A/B testing built-in (but unused)	Can add later if needed

Architecture

Stripe Webhook (immediate)          Daily Cron, 8am ET (scheduled)
         │                                    │
         ▼                                    ▼
  Welcome email                    Query premium_churches
  AI Starter Kit                   WHERE status IN ('active','preview')
  Payment failed                   AND activated_at IS NOT NULL
  Cancellation                              │
  Trial will end (day 11)                   ▼
         │                         For each church:
         ▼                           compute days_since_activation
   Send via Resend                   check SCHEDULE[plan]
   Log to lifecycle_emails_sent      check lifecycle_emails_sent (already sent?)
                                     check skip conditions (Supabase)
                                              │
                                              ▼
                                     Send via Resend
                                     Log to lifecycle_emails_sent

Database

CREATE TABLE lifecycle_emails_sent (
  id UUID PRIMARY KEY DEFAULT gen_random_uuid(),
  church_id UUID NOT NULL,
  email TEXT NOT NULL,              -- recipient email address
  email_key TEXT NOT NULL,          -- 'welcome_pro_chat', 'day2_nudge_pro', etc.
  sequence TEXT NOT NULL,           -- 'onboarding', 'winback', 'crosspromo_ps_cwa', etc.
  plan TEXT,                        -- plan at time of send (may change later)
  sent_at TIMESTAMPTZ NOT NULL DEFAULT now(),
  resend_message_id TEXT,           -- for delivery tracking
  UNIQUE(church_id, email_key)      -- PREVENTS DOUBLE-SENDS — this IS the state machine
);

CREATE INDEX idx_lifecycle_church ON lifecycle_emails_sent(church_id);
CREATE INDEX idx_lifecycle_sequence ON lifecycle_emails_sent(sequence);

The UNIQUE constraint on (church_id, email_key) is the entire state machine. No sequence table. No step tracking. The cron is idempotent — it can run 100 times safely.

Sequences

1. Onboarding — Starter Chat

Day	Key	Subject	Skip If
0	`welcome_starter_chat`	Welcome to ChurchWiseAI, [Pastor]!	— (webhook, immediate)
0	`starter_kit_starter`	Your AI Starter Kit is here	— (webhook, immediate)
2	`day2_setup_starter`	Quick tip: add your service times	`has_hours`
7	`day7_activation_starter`	Here's how churches are using their chatbot	`has_conversations`
13	`day13_trial_last_starter`	Your trial ends tomorrow — here's what you'd lose	—

2. Onboarding — Pro Chat

Day	Key	Subject	Skip If
0	`welcome_pro_chat`	Welcome to ChurchWiseAI Pro, [Pastor]!	— (webhook)
0	`starter_kit_pro`	Your AI Starter Kit is here	— (webhook)
2	`day2_setup_pro`	Quick win: add your first FAQ	`has_faqs`
5	`day5_theology_pro`	Make your chatbot sound like your church	`has_theology`
7	`day7_activation_pro`	35 tools your chatbot has — are you using them?	`has_conversations`
13	`day13_trial_last_pro`	Your Pro trial ends tomorrow — FAQs, analytics, embed gone	—
30	`day30_checkin_pro`	Your first month — how's it going?	—

3. Onboarding — Suite Chat

Day	Key	Subject	Skip If
0	`welcome_suite_chat`	Welcome to ChurchWiseAI Suite, [Pastor]!	— (webhook)
0	`starter_kit_suite`	Your AI Starter Kit is here	— (webhook)
2	`day2_setup_suite`	Quick win: add your first FAQ	`has_faqs`
5	`day5_theology_suite`	Make your chatbot sound like your church	`has_theology`
7	`day7_activation_suite`	39 tools, white-label ready — let's get you set up	`has_conversations`
13	`day13_trial_last_suite`	Your Suite trial ends tomorrow	—
30	`day30_checkin_suite`	Your first month — how's it going?	—

Day	Key	Subject	Trigger
0	`newsletter_welcome`	Welcome to ChurchWiseAI updates	Newsletter signup
2	`newsletter_why_ai`	Why churches are adopting AI in 2026	—
5	`newsletter_demo`	See a live chatbot in action	—

5. 7-Day AI Ministry Course (replaces MailerLite "7-Day AI Ministry Course")

Day	Key	Subject	Trigger
0	`course_day1`	Day 1: What AI can do for your church	Newsletter signup
1	`course_day2`	Day 2: Capturing prayer requests automatically	—
2	`course_day3`	Day 3: Never miss a visitor again	—
3	`course_day4`	Day 4: Your chatbot as a 24/7 church receptionist	—
4	`course_day5`	Day 5: Theological AI — respecting your tradition	—
5	`course_day6`	Day 6: What about sensitive conversations?	—
6	`course_day7`	Day 7: Getting started — your next step	—

6. Starter Kit Buyer Nurture (replaces MailerLite "CWA Starter Kit Buyer Nurture")

Day	Key	Subject	Trigger
0	`kit_delivery`	Your AI Starter Kit is ready to download	Purchase
3	`kit_followup`	Did you try the chatbot prompts?	—
7	`kit_upgrade`	Ready for the real thing? Starter Chat from $14.95/mo	—

Day	Key	Subject	Trigger
0	`xpromo_ps_cwa_0`	Your listing is live — now add AI to your church	PewSearch claim
5	`xpromo_ps_cwa_5`	Churches with AI chatbots see 3x more engagement	—
14	`xpromo_ps_cwa_14`	Special offer: ChurchWiseAI at founder pricing	—

Day	Key	Subject	Trigger
3	`xpromo_itw_sw`	Love illustrations? You'll love AI sermon prep	ITW Premium signup

Day	Key	Subject	Trigger
3	`xpromo_sw_itw`	Need illustrations for your sermon? Meet IllustrateTheWord	SermonWise signup

Day	Key	Subject	Trigger
7	`xpromo_cwa_share`	Your church AI is running — now automate your social media	CWA subscription active

11. Win-Back: Cancelled Customers (replaces MailerLite automation)

Day	Key	Subject	Trigger
3	`winback_3`	We miss you — here's what's new since you left	Cancellation
14	`winback_14`	Your church data is still saved — come back anytime	—
30	`winback_30`	Special offer: come back at 50% off for 3 months	—

Skip Conditions

const SKIP_CONDITIONS: Record<string, (churchId: string) => Promise<boolean>> = {
  has_hours: async (id) => {
    const { data } = await supabase.from('premium_churches')
      .select('custom_hours').eq('church_id', id).single();
    return data?.custom_hours && Object.keys(data.custom_hours).length > 0;
  },
  has_faqs: async (id) => {
    const { count } = await supabase.from('church_knowledge_base')
      .select('*', { count: 'exact', head: true })
      .eq('church_id', id).eq('type', 'faq');
    return (count ?? 0) > 0;
  },
  has_theology: async (id) => {
    const { data } = await supabase.from('organization_settings')
      .select('theological_lens').eq('church_id', id).single();
    return !!data?.theological_lens;
  },
  has_conversations: async (id) => {
    const { count } = await supabase.from('chatbot_conversations')
      .select('*', { count: 'exact', head: true })
      .eq('organization_id', id);
    return (count ?? 0) > 0;
  },
  has_embed: async (id) => {
    // Check if embed code was accessed/copied — may need a tracking event
    return false; // TODO: implement when tracking exists
  },
};

Templates

React Email components at src/lib/email-templates/lifecycle/:

lifecycle/
  _layout.tsx              — shared branded layout (Sacred Gold, Navy, Cream)
  welcome-starter-chat.tsx
  welcome-pro-chat.tsx
  welcome-suite-chat.tsx
  starter-kit.tsx
  setup-nudge.tsx          — plan-aware (different tips per plan)
  theology-nudge.tsx
  activation-nudge.tsx     — plan-aware (different tool counts)
  trial-last-day.tsx       — plan-aware (different features lost)
  first-month-checkin.tsx
  payment-failed.tsx
  cancellation.tsx
  newsletter-welcome.tsx
  course-day-[1-7].tsx
  kit-buyer-nurture.tsx
  crosspromo-ps-cwa.tsx
  crosspromo-itw-sw.tsx
  crosspromo-sw-itw.tsx
  crosspromo-cwa-share.tsx
  winback.tsx              — day-aware (different messaging per step)

MailerLite Template Settings (use these when sending via MailerLite campaigns API)

If we send any emails through MailerLite (e.g., Care broadcasts), use these settings:

Automatic preheader: ON — adds preheader with web version link
Automatic CSS inline: ON — some email clients strip <style> blocks
Automatic footer: ON — adds CAN-SPAM compliant footer with unsubscribe
Preferences link: INCLUDE — let subscribers update their preferences

For Resend-sent lifecycle emails, we must handle these ourselves:

Preheader: Include as hidden text at top of HTML template
CSS inlining: Use React Email's built-in inlining (already handles this)
Unsubscribe: Include unsubscribe link in footer for marketing emails (nudges, cross-promos, win-back). Transactional emails (welcome, payment failed, trial warning) don't legally require it but should include a preferences link.
Preferences link: Include in all emails — links to /admin/[token]?tab=settings&sub=notifications

Each template receives typed props:

type LifecycleEmailProps = {
  churchName: string;
  pastorName: string;
  plan: string;
  dashboardUrl: string;
  chatPageUrl: string;
  trialEndsAt?: string;
  featuresAtRisk?: string[];  // for trial-ending emails
  daysSinceSignup?: number;   // for nurture context
};

Cron Job

New file: src/app/api/cron/lifecycle-emails/route.ts

// Pseudocode
export async function GET(req: Request) {
  verifyVercelCron(req);

  // 1. Get all active/preview churches with activation date
  const churches = await getActiveChurches();

  // 2. Get all emails already sent
  const sentEmails = await getSentEmails(churches.map(c => c.church_id));

  // 3. For each church, check what's due
  for (const church of churches) {
    const daysSinceActivation = diffDays(now, church.activated_at);
    const schedule = SCHEDULE[church.plan] || SCHEDULE.starter_chat;

    for (const email of schedule) {
      if (daysSinceActivation < email.delay_days) continue;
      if (sentEmails.has(`${church.church_id}:${email.key}`)) continue;
      if (email.skipIf && await SKIP_CONDITIONS[email.skipIf](church.church_id)) continue;

      await sendAndLog(church, email);
    }
  }

  // 4. Also check non-church sequences (newsletter, course, kit buyers)
  await processNewsletterSequences();
  await processCourseSequences();
  await processKitBuyerSequences();

  // 5. Report to WatchTower
  return NextResponse.json({ processed: churches.length, sent: sentCount });
}

Vercel cron config in vercel.json:

{
  "crons": [
    { "path": "/api/cron/lifecycle-emails", "schedule": "0 13 * * *" }
  ]
}

(13:00 UTC = 8:00 AM ET)

Migration Plan

Build the system — table, cron, templates, Stripe webhook enhancements
Test with demo church — send test sequences, verify skip conditions, verify dedup
Disable MailerLite automations one by one — as each sequence is verified working
MailerLite stays active for: newsletter subscriber management (forms, groups), Care tab broadcasts
Monitor via WatchTower — add lifecycle email health check to daily audit

MailerLite Automations to Disable (9 total)

#	Automation	Status	Created	Replacement
1	CWA Newsletter Welcome Sequence	Active	2025-10-17	Sequence #4 (newsletter_welcome)
2	7-Day AI Ministry Course	Active	2025-10-17	Sequence #5 (course_day1-7)
3	CWA Starter Kit Buyer Nurture	Active	2025-10-31	Sequence #6 (kit_delivery/followup/upgrade)
4	Cross-Promo: PewSearch → CWA	Active	2026-03-14	Sequence #7 (xpromo_ps_cwa)
5	Cross-Promo: ITW → SermonWise	Active	2026-03-14	Sequence #8 (xpromo_itw_sw)
6	Cross-Promo: SermonWise → ITW	Active	2026-03-14	Sequence #9 (xpromo_sw_itw)
7	Cross-Promo: CWA → ShareWise	Active	2026-03-14	Sequence #10 (xpromo_cwa_share)
8	Win-Back: Cancelled Customers	Active	2026-03-14	Sequence #11 (winback)
9	CWA Trial Nurture	PAUSED/Incomplete	2025-11-15	Sequences #1-3 (onboarding per plan) — this is exactly what we're building, but per-plan and with skip conditions

Note: The CWA Trial Nurture was started Nov 2025 but never completed. It was the original attempt at what our lifecycle system now does properly — plan-specific onboarding with smart skip conditions. Delete it from MailerLite after our system is live.

Files to Create/Modify

New files:

src/app/api/cron/lifecycle-emails/route.ts — the cron job
src/lib/lifecycle-emails.ts — sequence definitions, skip conditions, send logic
src/lib/email-templates/lifecycle/_layout.tsx — shared branded layout
src/lib/email-templates/lifecycle/*.tsx — ~25 email templates
pewsearch/migrations/xxx_lifecycle_emails_sent.sql — table creation

Modified files:

src/app/api/stripe/webhook/route.ts — enhance to send immediate lifecycle emails
src/lib/email.ts — may need to add Resend helpers
vercel.json — add cron schedule

Testing

Use demo church (churchwiseai-demo, UUID 00000000-0000-4000-a000-000000000001)
Create test entries in lifecycle_emails_sent to verify dedup
Manually trigger cron via GET /api/cron/lifecycle-emails with cron auth
Verify Resend delivery in Resend dashboard
Check WatchTower alerts for failures
Test skip conditions by toggling church data on/off

Problem​

Email Trigger Points​

Solution​

Why Not MailerLite​

Architecture​

Database​

Sequences​

1. Onboarding — Starter Chat​

2. Onboarding — Pro Chat​

3. Onboarding — Suite Chat​

4. Newsletter Welcome (replaces MailerLite "CWA Newsletter Welcome Sequence")​

5. 7-Day AI Ministry Course (replaces MailerLite "7-Day AI Ministry Course")​

6. Starter Kit Buyer Nurture (replaces MailerLite "CWA Starter Kit Buyer Nurture")​

7. Cross-Promo: PewSearch → CWA (replaces MailerLite automation)​

8. Cross-Promo: ITW → SermonWise (replaces MailerLite automation)​

9. Cross-Promo: SermonWise → ITW (replaces MailerLite automation)​

10. Cross-Promo: CWA → ShareWise (replaces MailerLite automation)​

11. Win-Back: Cancelled Customers (replaces MailerLite automation)​

Skip Conditions​

Templates​

MailerLite Template Settings (use these when sending via MailerLite campaigns API)​

Cron Job​

Migration Plan​

MailerLite Automations to Disable (9 total)​

Files to Create/Modify​

Testing​