paywall-upgrade-cro

Before designing or optimizing a paywall, answer these questions:

1. What triggers this paywall? (Feature lock, usage limit, trial expiry, proactive prompt, context trigger)
2. What percentage of active users see this paywall per week? (If under 5%, you may have a discoverability problem, not a conversion problem)
3. What is the current paywall-to-upgrade conversion rate? (Benchmarks: feature lock 3-8%, usage limit 5-15%, trial expiry 15-40%)
4. What value has the user experienced before hitting this paywall? (More value = higher conversion potential)
5. Can the user dismiss the paywall and continue using the product? (Hard vs soft paywall)
6. What plan/pricing is shown? (Single plan, multiple plans, usage-based)
7. Is the paywall personalized to the user's behavior? (Generic vs personalized)
8. How many times has this user seen this paywall before? (First impression vs repeated exposure)

---

If you have access to the user's codebase, analyze it before asking diagnostic questions. Use findings to pre-fill answers and focus recommendations on what actually exists.

1. Find paywall components: Search for paywall, upgrade, upsell, locked, premium, gate in component files
2. Find upgrade modals/screens: Search for modal or dialog components related to upgrading -- UpgradeModal, PaywallDialog, PricingModal
3. Check trigger logic: Search for conditions that show paywalls -- plan !== 'pro', isFreePlan, usage > limit, trialExpired
4. Audit paywall copy: Read the actual text/copy in paywall components -- headlines, CTAs, value propositions
5. Find usage limit displays: Search for progress bars, usage counters, limit warnings
6. Check CTA buttons: Find upgrade button components -- what do they say? Where do they link?
7. Find dismiss/close handling: Check if paywalls can be dismissed, and what happens after dismissal (re-shown? when?)
8. Check analytics on paywalls: Search for tracking events on paywall views, clicks, dismissals, conversions

Report: inventory all upgrade touchpoints, their triggers, copy, and any tracking.

For a full growth audit, install [skene-skills](https://github.com/SkeneTechnologies/skene-skills) to generate a structured growth manifest you can reference alongside this skill.

---

2.1 Feature Lock Paywall

Trigger: User clicks or attempts to use a gated feature.

When it works best: When the locked feature is highly desirable and the user already understands its value from seeing it in the UI, documentation, or other users' outputs.

Design principles:

• Show a preview or demo of the feature in action
• Explain what the feature does and why it matters for the user's workflow
• Include a before/after comparison when possible
• Show which plan unlocks this feature
• Allow easy dismissal back to what the user was doing

Copy framework:

```

Headline: [Feature Name] is available on [Plan Name]

Subhead: [One sentence describing the user benefit, not the feature itself]

Body: [2-3 bullet points showing what they can do with this feature]

Social proof: [X teams/users upgraded for this feature this month]

CTA primary: Upgrade to [Plan] -- [Price]/mo

CTA secondary: Learn more | Maybe later

```

Template:

```

--- FEATURE LOCK PAYWALL ---

Trigger: User clicks [feature name]

Location: [Where in the product this appears]

Visual: [Screenshot/preview/demo of the feature in action]

Headline: Unlock [Feature Name] with [Plan Name]

Subhead: [Specific benefit -- e.g., "Save 3 hours per week with automated reports"]

What you get:

• [Benefit 1 -- framed as outcome, not feature]
• [Benefit 2]
• [Benefit 3]

Social proof: [Number] teams upgraded this [time period]

Primary CTA: Start [Plan] -- $[price]/mo

Secondary CTA: See all plans | Dismiss

Dismiss behavior: [Return to previous screen / show feature as locked]

```

2.2 Usage Limit Paywall

Trigger: User hits a plan-imposed usage ceiling (storage, API calls, team members, projects, exports).

When it works best: When the user is actively engaged and the limit directly blocks continued productivity. The user has already demonstrated value from usage.

Design principles:

• Show current usage vs. limit clearly (progress bar, fraction)
• Frame the upgrade around unlocking continued momentum, not punishment
• Show the value they have already received (you have created X, processed Y)
• Offer the next tier with clear headroom
• Consider offering a temporary bump (e.g., "Need a few more? Get 5 extra free this month")

Copy framework:

```

Headline: You've used [X] of [Y] [resource]

Subhead: [Acknowledge their productivity -- e.g., "Great progress! You've built X this month."]

Body: Upgrade to [Plan] for [new limit or unlimited] [resource]

Value frame: That's just $[price per unit] per [resource]

CTA primary: Upgrade to [Plan]

CTA secondary: Manage usage | See plans

```

2.3 Trial Expiration Paywall

Trigger: Free trial period ends.

When it works best: When the user has activated and experienced meaningful value during the trial. Conversion is highly correlated with trial activation quality.

Design principles:

• Recap the value the user received during the trial (personalized usage summary)
• Clearly state what they will lose or what will be downgraded
• Offer multiple plan options with clear differentiation
• Consider a trial extension for users who haven't activated yet
• Create urgency without manipulation (countdown, clear date)

Copy framework:

```

Headline: Your [Product] trial ends [today/in X days]

Subhead: Here's what you accomplished during your trial:

Value recap: [Personalized stats -- files created, time saved, team members added]

Loss frame: Without [Plan], you'll lose access to: [key features list]

Plans: [Show 2-3 plan options with recommended plan highlighted]

CTA primary: Continue with [Recommended Plan]

CTA secondary: See all plans | Downgrade to free

```

2.4 Time-Based Prompt

Trigger: Proactive upgrade suggestion based on usage duration or frequency, not a hard block.

When it works best: When users have been on a free plan for a significant period and show consistent engagement. The goal is to introduce upgrade consideration without blocking workflow.

Design principles:

• Non-blocking (banner, tooltip, or subtle prompt)
• Acknowledge the user's tenure and engagement
• Introduce specific premium features relevant to their usage
• Easy to dismiss with no negative consequence
• Use progressive disclosure (first mention, then deeper pitch on subsequent views)

Copy framework:

```

Headline: You've been using [Product] for [X weeks/months] -- nice!

Subhead: Did you know [Plan] includes [feature relevant to their usage pattern]?

CTA: Learn more | Not now

```

2.5 Context-Triggered Paywall

Trigger: Upgrade prompt at a moment of high intent or value delivery.

When it works best: When the user just completed a meaningful action, achieved a result, or is in a flow where premium features would amplify their success.

Examples:

• User exports a report (prompt for branded/custom exports)
• User adds a third team member (prompt for team plan)
• User completes their tenth project (prompt for unlimited projects)
• User shares content publicly (prompt for custom domain/branding)

Design principles:

• Tie the prompt directly to the action they just took
• Show how the upgrade would enhance the specific outcome they achieved
• Keep it contextual and brief (tooltip, inline, or small modal)
• Celebrate the achievement before pitching the upgrade

---

3.1 Show Value, Not Just Price

Users should understand what they are buying, not just what it costs. Every paywall must answer: "What will I be able to do after upgrading that I cannot do now?"

Checklist:

• [ ] Paywall shows specific features/capabilities unlocked
• [ ] Benefits are framed as outcomes (save time, grow revenue) not features (API access, SSO)
• [ ] If possible, show personalized value based on user's actual usage
• [ ] Price is contextualized (per user/month, equivalent to cost of X)

3.2 Make It Easy to Dismiss

Trapping users in a paywall destroys trust. Every paywall must have a clear, visible way to decline.

Checklist:

• [ ] Dismiss/close button is visible and standard-sized
• [ ] Clicking outside the modal closes it (if modal)
• [ ] Escape key closes it (if modal)
• [ ] Dismissing returns the user to their previous context
• [ ] No dark patterns (e.g., "No, I don't want to grow my business")

3.3 Personalize Based on Usage

A generic paywall converts at 2-5%. A personalized paywall converts at 5-15%.

Personalization layers:

1. Feature relevance: Show features related to what they actually use
2. Usage stats: "You've created 47 projects this month"
3. Team context: "3 of your team members are on the free plan"
4. Industry/role: Different value props for different personas
5. Engagement level: More aggressive for power users, lighter for casual users

3.4 Include Social Proof

Social proof reduces perceived risk and creates urgency.

Types to include:

• "[X] teams upgraded this month"
• "[X]% of users like you choose [Plan]"
• Customer logos (if B2B)
• Brief testimonial quote
• Star rating or G2/Capterra score

3.5 Offer Multiple Options

Never present "upgrade or leave" as the only choice. Offer graduated options.

Option structure:

• Primary CTA: Recommended plan (highlighted)
• Secondary CTA: Alternative plan or "see all plans"
• Tertiary CTA: Dismiss / "Not now" / "Remind me later"
• Optional: Trial extension, limited-time offer, annual discount callout

---

Team expansion is a major revenue driver in B2B PLG. Design specific prompts for team growth moments.

Trigger moments:

• New team member is invited
• Collaboration feature is used for the first time
• User shares a project with someone outside the team
• Admin views team management page
• Team hits seat limit

Copy framework for team upgrade:

```

Headline: Your team is growing!

Subhead: Add [Name] to your [Plan] workspace for $[price]/seat/month

Value: Teams on [Plan] collaborate [X]% faster with [feature list]

CTA: Add seat | Upgrade team plan

```

---

Mobile paywalls have unique constraints: smaller screens, different interaction patterns, app store payment flows.

5.1 Bottom Sheet

• Slides up from the bottom, covers 60-80% of screen
• Good for quick decisions with 2-3 plan options
• Easy to dismiss with swipe down
• Best for: feature locks, quick upgrades

5.2 Full-Screen

• Takes over the entire screen
• Good for trial expiration or comprehensive plan comparison
• Must have clear close/back button
• Best for: trial expiry, onboarding upgrade prompt

5.3 Card-Style

• Horizontally scrollable cards showing plan tiers
• Good for comparing multiple plans
• Compact but informative
• Best for: plan selection, annual vs monthly toggle

Mobile-specific considerations:

• Respect platform payment guidelines (Apple/Google)
• Show pricing in local currency
• Minimize text, maximize visual hierarchy
• Use system-native UI patterns for familiarity
• Test thumb-reach for CTA placement

---

What to Test (Priority Order)

1. Paywall timing: When in the user journey the paywall appears
2. Copy: Headline and value proposition framing
3. Social proof: Type and placement of social proof elements
4. Pricing display: Monthly vs annual, per-user vs flat, showing vs hiding prices
5. Layout: Number of plans shown, visual hierarchy, image/illustration usage
6. CTA text: "Start free trial" vs "Upgrade now" vs "See plans"
7. Dismiss behavior: What happens when user declines

Testing Framework

```

Test Name: [Descriptive name]

Hypothesis: Changing [element] from [control] to [variant] will [increase/decrease] [metric] by [X]% because [reason]

Primary metric: Paywall conversion rate

Secondary metrics: Revenue per impression, time to conversion, plan mix

Segment: [Which users see this test]

Duration: [Minimum 2 weeks or 500 conversions per variant]

```

Statistical Rigor

• Minimum sample: 500 paywall views per variant (1,000+ preferred)
• Minimum conversions: 50 per variant for reliable results
• Run for at least one full business cycle (typically 1-2 weeks)
• Check for novelty effects by comparing week 1 vs week 2

---

Avoid these common paywall mistakes:

| Anti-Pattern | Why It Fails | Better Alternative |

|---|---|---|

| Aggressive popup on first visit | User has no context for value | Wait until user experiences value |

| Blocking core product functionality | Users cannot evaluate the product | Gate advanced features, keep core free |

| Hidden dismiss button | Destroys trust, increases churn | Clear, visible close button |

| Unclear pricing | Creates anxiety and abandonment | Transparent pricing with context |

| Same paywall for everyone | Mismatched value proposition | Personalize by usage and segment |

| Too many paywalls per session | Nag fatigue, user resentment | Frequency caps (max 1-2 per session) |

| Guilt-trip dismiss copy | "No, I hate saving money" feels manipulative | Neutral dismiss: "Not now" or "Maybe later" |

| No free option shown | All-or-nothing feels risky | Show free plan as a valid choice |

---

Primary Metrics

| Metric | Formula | Benchmark |

|---|---|---|

| Paywall View Rate | Users who see paywall / Total active users | 20-60% |

| Paywall Conversion Rate | Users who upgrade / Users who see paywall | 3-15% (varies by type) |

| Revenue Per Paywall Impression (RPPI) | Total upgrade revenue / Total paywall impressions | Track trend, not absolute |

| Time from First Paywall to Conversion | Median days between first paywall view and upgrade | 7-30 days |

Conversion Rate Benchmarks by Paywall Type

| Paywall Type | Low | Median | High |

|---|---|---|---|

| Feature lock | 2% | 5% | 10% |

| Usage limit | 5% | 10% | 20% |

| Trial expiration | 15% | 25% | 45% |

| Time-based prompt | 0.5% | 2% | 5% |

| Context-triggered | 3% | 7% | 15% |

Diagnostic Metrics

• Paywall dismiss rate: High dismiss rate (>90%) suggests poor timing or value proposition
• Repeat paywall view rate: Users seeing the paywall multiple times before converting (or churning)
• Post-paywall churn: Users who churn within 7 days of seeing a paywall (indicates paywall is damaging)
• Plan selection distribution: Which plans users choose from the paywall (informs pricing and packaging)

---

When designing a paywall, produce this specification:

```

# Paywall Design Specification

• Paywall type: [Feature lock / Usage limit / Trial expiry / Time-based / Context-triggered]
• Trigger: [Specific user action or condition]
• Target segment: [Which users see this paywall]
• Frequency: [How often this can appear per user per time period]

• What value has the user experienced before this moment?
• What is the user trying to accomplish right now?
• What emotional state is the user likely in?

• Headline: [...]
• Subhead: [...]
• Body/bullets: [...]
• Social proof: [...]
• Primary CTA: [...] (button text + destination)
• Secondary CTA: [...] (button text + destination)
• Dismiss behavior: [What happens when user closes]

• Dynamic elements: [What changes based on user data]
• Data sources: [Where the personalization data comes from]
• Fallback: [What shows if personalization data is unavailable]

• Format: [Modal / Banner / Inline / Bottom sheet / Full-screen]
• Size: [Dimensions or responsive behavior]
• Visual elements: [Illustrations, screenshots, icons]
• Animation: [Entry/exit behavior]

• Primary metric: [Conversion rate target]
• Secondary metrics: [Revenue, plan mix, dismiss rate]
• Success criteria: [What constitutes success for this paywall]

• Hypothesis: [...]
• Variants: [Control vs variant description]
• Sample size needed: [...]
• Duration: [...]

```

---

```

User hits a gated moment

├── Is the user on a free trial?

│ ├── Yes, trial active → Soft context-triggered prompt (non-blocking)

│ └── Yes, trial expired → Trial expiration paywall (blocking)

├── Is the user on a free plan?

│ ├── Hit a usage limit? → Usage limit paywall

│ ├── Clicked a locked feature? → Feature lock paywall

│ ├── High engagement, no upgrade intent? → Time-based prompt

│ └── Just completed a high-value action? → Context-triggered prompt

└── Is the user on a paid plan?

├── Hit plan limit? → Usage limit paywall (upgrade tier)

├── Using a feature from higher tier? → Feature lock paywall

└── Team growing? → Seat/team upgrade prompt

```

---

Related skills: feature-gating, pricing-strategy, trial-optimization, in-product-messaging