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IllustrateTheWord Premium — Founder Interview Input File

Product: IllustrateTheWord Premium (itw_premium / itw_premium_annual) Purpose: Define exactly what an ITW Premium customer sees at every touchpoint. How to use: Fill in YOUR ANSWER under each question. Then in a new Claude session, say: "Read knowledge/acceptance/decisions/itw-premium-interview-prompt.md and write the complete ITW Premium acceptance spec at knowledge/acceptance/itw-premium.md."

Reference: knowledge/acceptance/starter-chat.md is the completed example to follow for structure. Codebase: C:\dev\sermon-illustrations/ URL: illustratetheword.com Pricing: $9.95/mo (price_1T99TPFaoK5IPzNoCqX8hEik) | Annual (USD) $99.50/yr (price_1TM4lTFaoK5IPzNoTbothyxa on canonical prod_U7OFzu0vIWOFuz) | Annual (CAD) $129/yr (price_1TWJiFFaoK5IPzNoepcX1HGr)

Note: price_1T99U5FaoK5IPzNobdKJhCyJ was the old annual price on the split product prod_U7OGpFN8OR2LST (archived 2026-05-12 per FA-002 closeout). Do not reference in new code. Auth: Supabase Auth (email/password + Google OAuth)

Context for answers: ITW is a sermon illustration library — NOT a SaaS dashboard. There is no admin panel. Customers browse, search, save, and copy illustrations. The three tiers of content access are: public (anonymous), free_signup (free account required), and premium (paid subscription required). Premium unlocks ~14% of the library that includes premium content types (movie_analogy, devotional, lens_perspective, application_point, show_dont_tell_prompt, spiritual_discipline, character_profile, vivid_retelling, tv_analogy) and high-quality sermon_illustration entries.

Section A: Discovery & Marketing​

Q1: How does a pastor typically find IllustrateTheWord? Rank or check the primary discovery paths:

YOUR ANSWER (check all that apply, star the most likely):

  • Google search (e.g., "sermon illustrations for pastors")
  • Link from ChurchWiseAI.com / churchwiseai.com
  • Link from PewSearch.com
  • Social media / YouTube
  • Word of mouth from another pastor
  • Other:

Q2: What does the ITW homepage show? Is there a visible Free vs Premium distinction above the fold, or does a new visitor just see the library and discover the gate when they click an illustration?

YOUR ANSWER:

Prompts to consider:

  • Is there a hero section that explains the pricing tiers up front?
  • Is there a "See Pricing" or "Upgrade to Premium" CTA on the homepage?
  • Does the homepage feel like a content browse experience, or a marketing landing page?

Q3: Is there a dedicated pricing page at illustratetheword.com/pricing (or similar)? If yes, what does it show — just the two tiers (Free vs Premium), or does it also mention the Free Signup middle tier?

YOUR ANSWER:

Q4: Any SEO-driven landing pages for specific topics or scripture passages (e.g., /illustrations/grace, /illustrations/john-3-16)? Do these pages show locked content, or only public-tier illustrations?

YOUR ANSWER:

Section B: Sign-Up & Onboarding​

Q5: The sign-up flow — when does Stripe get involved? Options:

YOUR ANSWER (pick one):

  • Free account first (email/Google OAuth), then upgrade prompt for Premium content
  • Straight to checkout for Premium ($9.95/mo or $99.50/yr) — no free account step
  • Free account created at checkout, subscription attached at the same time
  • Other:

Q6: What fields are required to create a free account? (e.g., name, email, password, church name, denomination?)

YOUR ANSWER:

Q7: Is there a free trial for ITW Premium? (CWA chat plans have 14 days free — does ITW offer anything similar, or is it pay immediately?)

YOUR ANSWER (pick one):

  • No trial — pay $9.95 immediately on subscribe
  • 7-day free trial
  • 14-day free trial (same as CWA)
  • Other:

Q8: Welcome email — what does it say? Specifically:

  • Subject line?
  • "3 things to do first" equivalent (or is it simpler — just "you're in, here's the library")?
  • Does it link to a specific part of the library (e.g., "Start with this week's lectionary readings")?
  • Does it mention the ChurchWiseAI ecosystem at all?

YOUR ANSWER:

Q9: First login experience after subscribing — what changes visually? Options:

YOUR ANSWER (describe what the pastor sees):

  • Is there a "Welcome, you're Premium!" banner or modal?
  • Does the navigation change (e.g., a "My Library" or "Favorites" section appears)?
  • Are previously locked illustrations now visibly unlocked, or does the pastor need to search to discover them?

Section C: Free vs Premium Experience​

Q10: What can a completely anonymous (not logged in) visitor see and do?

YOUR ANSWER:

Prompts to consider:

  • Can they read full public-tier illustrations (~18% of library)?
  • Can they see the title/teaser of free_signup and premium illustrations in search results?
  • Can they search and filter?
  • Can they save/bookmark anything?

Q11: What can a Free Signup user (logged in, not paying) see and do beyond anonymous?

YOUR ANSWER:

Prompts to consider:

  • Full content for free_signup-tier illustrations (~68% of library)?
  • Can they see the title/teaser of premium illustrations in search results?
  • Can they save favorites?
  • Any other perks for free accounts?

Q12: What does Premium unlock beyond Free Signup?

YOUR ANSWER:

Prompts to consider:

  • Full content for premium-tier illustrations (~14% — movie analogies, devotionals, lens perspectives, vivid retellings, etc.)?
  • Any other features (downloads, print-friendly view, collections, unlimited favorites, etc.)?
  • Priority access to new illustrations as they're added?

Q13: How is the gate displayed when a Free Signup user hits a Premium illustration? Options:

YOUR ANSWER (pick one or describe):

  • Full content blurred with an "Upgrade to Premium" overlay
  • Teaser/first paragraph only, then hard cut with upgrade CTA
  • Lock icon on the card in search results, locked detail page
  • Redirect to upgrade/pricing page
  • Something else:

What does the CTA say? (e.g., "Unlock this illustration — $9.95/mo", "Upgrade to Premium", "Get full access")

Q14: How is the gate displayed when an anonymous visitor hits a Free Signup illustration? (Same question, different tier boundary)

YOUR ANSWER:

What does the CTA say? (e.g., "Sign up free to read this", "Create a free account", "Join free")

Q15: Copy / print / download features — are any of these available, and at which tier?

YOUR ANSWER (describe each or mark N/A):

  • Copy to clipboard button: [ ] Anonymous [ ] Free Signup [ ] Premium only [ ] N/A
  • Print-friendly view: [ ] Anonymous [ ] Free Signup [ ] Premium only [ ] N/A
  • Download as PDF/Word: [ ] Anonymous [ ] Free Signup [ ] Premium only [ ] N/A
  • Other export options:

Section D: Content & Library​

Q16: How are illustrations organized for browsing? Check all navigation options that exist:

YOUR ANSWER (check all that apply):

  • Topic/theme (e.g., Grace, Forgiveness, Hope)
  • Scripture reference (Old Testament, New Testament, book, passage)
  • Content type (sermon illustration, movie analogy, devotional, quote, etc.)
  • Liturgical season (Advent, Lent, Easter, Pentecost, etc.)
  • Theological tradition / TheoLens (Reformed, Catholic, Evangelical, etc.)
  • Emotion (e.g., conviction, hope, wonder)
  • Date added / newest first
  • "This Sunday" lectionary view (RCL calendar)
  • Other:

Q17: How many total illustrations are in the library? And how often are new ones added?

YOUR ANSWER:

Prompts to consider:

  • Approximate total (the codebase mentions 50,000+ — is this what's communicated publicly, or a different number?)
  • New additions: weekly? Monthly? On a lectionary cycle?
  • Is there a "New this week" or "Recently added" section?

Q18: Is there any personalization or denomination-specific filtering?

YOUR ANSWER:

Prompts to consider:

  • Can a pastor set their denomination/tradition in their profile, and see illustrations filtered to match?
  • Does the site recommend illustrations based on browsing history?
  • Is the TheoLens filter (17 traditions) prominently surfaced, or buried?
  • "This Sunday" lectionary — does it auto-detect the current week, or does the pastor pick the date?

Q19: Can pastors save favorites or build collections?

YOUR ANSWER:

Prompts to consider:

  • Is there a "Save" or "Bookmark" button on each illustration?
  • Is saving available at all tiers (Free Signup, Premium) or Premium only?
  • Can saved illustrations be organized into named collections/folders?
  • Is there a "My Saved Illustrations" page or tab?
  • Is there a limit on how many can be saved (e.g., 10 for free, unlimited for Premium)?

Section E: Account & Settings​

Q20: What does the account settings page contain? Check all sections that exist:

YOUR ANSWER (check all that apply):

  • Name / display name
  • Email address (with change flow)
  • Password change
  • Church name
  • Denomination / theological tradition preference
  • Notification preferences (e.g., "email me new illustrations every Sunday")
  • Billing / subscription management (link to Stripe Customer Portal)
  • Cancel subscription button
  • Delete account
  • Other:

Q21: How does a Premium subscriber cancel? Step by step:

YOUR ANSWER:

Prompts to consider:

  • Is there a "Cancel Subscription" button in account settings, or do they go to a Stripe Customer Portal?
  • What happens immediately: access continues until billing period ends, or cut off immediately?
  • Is there a confirmation step / "are you sure" with a retention offer?
  • What does the email say after cancellation?

Q22: Can a subscriber switch between monthly ($9.95) and annual ($99.50)? If yes, how?

YOUR ANSWER:

Prompts to consider:

  • Is there a toggle in account settings between monthly and annual?
  • Or does switching go through the Stripe Customer Portal?
  • Does switching from monthly to annual prorate/apply a credit?
  • Is switching from annual to monthly allowed mid-term?

Section F: Cross-Sell to ChurchWiseAI​

Q23: Is there any ChurchWiseAI promotion within the ITW site? If yes, where and what does it say?

YOUR ANSWER:

Prompts to consider:

  • Is there a banner, sidebar widget, or footer note mentioning the voice agent or chatbot?
  • The codebase has a ChurchWiseAIPromo component — is this shown on illustration pages, the homepage, or specific pages only?
  • What does the CTA say? (e.g., "Give your church an AI assistant — ChurchWiseAI")

Q24: Does ITW mention the chatbot or voice agent anywhere by name or feature description?

YOUR ANSWER:

Q25: Is there any bundle discount or combined offering for ITW Premium + a ChurchWiseAI plan (chat or voice)?

YOUR ANSWER (pick one):

  • No — they are priced independently, no bundle
  • Yes — there is a discount if you have both (describe):
  • Not yet, but planned — describe any future intent:

Section G: Lifecycle Emails & Billing Events​

Q26: If ITW has a free trial — what emails does the pastor receive during the trial?

YOUR ANSWER (describe each email or mark N/A if no trial):

  • Day 0 (trial start): subject line + key content
  • Day 7 (mid-trial reminder, if 14-day): subject + key content
  • Day 11-12 (trial ending soon): subject + key content
  • Day 14 (trial expired): subject + key content

Q27: Payment failed — what happens and what does the pastor see?

YOUR ANSWER:

Prompts to consider:

  • Email: immediate payment failed notice, then retry notices at Day 3, 7?
  • Access: immediate downgrade to Free Signup on failure, or grace period (how many days)?
  • Dashboard/site: is there a banner saying "Your payment failed — update billing"?
  • What's the CTA in the email / on the site? (Link to Stripe Customer Portal?)

Q28: After cancellation — what happens to the pastor's saved/bookmarked illustrations?

YOUR ANSWER:

Prompts to consider:

  • Saved favorites: are they preserved in the database even after downgrade to free?
  • Premium content they've saved: can they still see the title/teaser but not the full content?
  • Or are their favorites cleared on cancel?

Q29: Re-subscription — if a pastor cancels and comes back later, what happens?

YOUR ANSWER:

Prompts to consider:

  • Do they get their saved favorites back?
  • Is the re-subscribe flow the same as the initial subscribe (standard Stripe checkout)?
  • Is there a "Welcome back!" email, or the same welcome as a new subscriber?
  • Any re-subscribe discount or incentive offered?

Additional Notes​

Anything else about the ITW Premium experience that isn't covered above — edge cases, known issues, things that aren't built yet but should be noted:

YOUR NOTES: