Marketing SkillsView repo

Marketing Skill

Paywalls

Designs the in-product upgrade moments — feature gates, usage-limit screens, trial-expiration prompts — that convert free users to paid after they've already felt the value. Point your agent at it when free users won't upgrade and you need paywalls that feel helpful, not pushy.

Maintained by Corey Hainesv2.0.0Updated 2026-05-131 references
npx skills add coreyhaines31/marketingskills

Installs the full library — Paywalls included

MarkdownView source

An in-app paywall converts when it appears after the user has experienced real value, frames the upgrade around a benefit they now want, and leaves an easy way to say no. Trigger it at natural moments — hitting a usage limit, clicking a paid-only feature, or a trial ending — never during onboarding or mid-flow. A strong paywall screen has a benefit-led headline ("Unlock [feature] to [outcome]"), a preview of what they're missing, a simple free-vs-paid comparison, social proof, one clear CTA, and a visible "Not now" escape hatch. Cap frequency to once per session with a multi-day cool-down after dismissal, and avoid dark patterns like hidden close buttons or guilt-trip copy — they cost you the trust you need for a later conversion.

When to use it

Your agent reaches for this skill when you ask for things like:

“paywall,”“upgrade screen,”“upgrade modal,”“upsell,”“feature gate,”“convert free to paid,”“freemium conversion,”“trial expiration screen,”

What's inside

The playbook covers

Initial AssessmentCore PrinciplesPaywall Trigger PointsPaywall Screen ComponentsSpecific Paywall TypesTiming and FrequencyUpgrade Flow OptimizationA/B TestingAnti-Patterns to AvoidTask-Specific Questions

Reference library — 1 deep-dives

Paywall Experiment IdeasComprehensive list of A/B tests and experiments for paywall optimization.

See it in action

You ask

Help me design the upgrade paywall for our project management tool. Free users can have 3 projects, and we want to show an upgrade screen when they try to create a 4th project.

The skill delivers
Usage-limit paywall (4th project attempt)

You've used all 3 free projects 🎉 ▓▓▓▓▓▓▓▓▓▓ 3 of 3 Upgrade to Pro for unlimited projects — plus advanced analytics and priority support. Free: 3 projects → Pro: Unlimited "We stopped juggling and just built." — 12,000+ teams on Pro [ Upgrade to Pro — $29/mo ] [ Delete a project ] · Maybe later

FAQ

When should I show an upgrade paywall?

After a value moment, before frustration — right when someone has felt the product work. The proven triggers are feature gates (clicking a paid-only feature), usage limits (hitting a threshold), and trial expiration. Don't show paywalls during onboarding, mid-task, or repeatedly after someone dismisses one.

How do I improve a low trial-expiration conversion rate?

Replace the generic "your trial expired" screen with a personalized one: summarize what they built and accomplished during the trial (endowment effect), use loss framing to show exactly what they'd lose, highlight the specific features they actually used, offer clear plan options, and add social proof from similar users who upgraded. A weak, one-size-fits-all screen with no urgency is usually why conversion is low.

What paywall anti-patterns should I avoid?

Dark patterns (hidden or tiny close buttons, confusing opt-out language, guilt-trip "No, I don't want to save money" copy) and conversion killers (asking before value is delivered, blocking critical flows, and prompting too frequently). Always give a clear escape hatch and respect the no — good paywalls feel helpful, not tricky.

Related skills

churn preventionFor cancel flows, save offers, and reducing churn post-upgradecroFor public pricing page optimizationonboardingFor driving to aha moment before upgradeab testingFor testing paywall variations

Build a tool for this workflow?

Marketers run this skill mid-task — the exact moment your tool matters. Partner tiers put your tool inside the skill their agent runs.

See partner tiers