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calwizz-spec-freemium

3 min read

CalWizz Freemium Plan Spec

Overview

Define free vs paid tiers to convert trial users to paying customers while providing enough value in the free tier to drive word-of-mouth.

Current State

  • Pricing: 20/year
  • Trial: 14-day free trial, then paywall
  • Problem: Users may not see enough value in 14 days to convert

Proposed Tiers

🆓 Free Forever

Target: Casual users who want basic calendar visibility

FeatureFree Limit
Calendar connections1
Date rangeLast 30 days only
Basic stats✅ Total meeting hours, meeting count
Meeting breakdown✅ By day of week
Schedule Health Score❌
Time distribution charts❌
Meeting categories❌
Export data❌
Email recaps❌
Historical data❌ (365 days max)

Value prop: “See how much time you’re spending in meetings this month”

💼 Pro (20/year)

Target: Professionals who want to optimize their calendar

FeaturePro
Calendar connections3
Date rangeUnlimited history
Basic stats✅
Meeting breakdown✅ All views
Schedule Health Score✅
Time distribution charts✅
Meeting categories✅ Auto + custom
Export data✅ CSV/PDF
Email recaps❌
Focus time analysis✅
Trend comparisons✅ Week-over-week, month-over-month

Value prop: “Understand and improve your meeting habits”

🏢 Team (Future - $15/user/month)

Target: Managers who want team calendar insights

FeatureTeam
Everything in Pro✅
Team dashboard✅
Email recaps✅
Meeting overlap analysis✅
Team schedule health✅
Manager reports✅
SSO/SAML✅
Priority support✅

Value prop: “Protect your team’s time”

Free → Pro Upgrade Triggers

Soft Gates (Show preview, prompt upgrade)

  1. After 30 days: “Want to see your full history? Upgrade to Pro”
  2. Schedule Health Score: Show grayed-out score with “Unlock with Pro”
  3. Export: “Export to CSV available on Pro”
  4. Second calendar: “Connect more calendars with Pro”

Hard Gates (Block functionality)

  1. Calendar connections beyond 1
  2. Date ranges beyond 30 days
  3. Email recap configuration
  4. Advanced charts and breakdowns

Implementation Checklist

Database Changes

  • Add plan field to users table (free/pro/team)
  • Add plan_expires_at for trial/subscription tracking
  • Add calendars_limit based on plan

Backend Changes

  • Create plan check middleware
  • Limit date range queries for free users
  • Gate advanced features behind plan check
  • Update Stripe integration for plan changes

Frontend Changes

  • Add upgrade prompts at gate points
  • Show plan badge in header/settings
  • Create upgrade modal with feature comparison
  • Add “Why upgrade?” tooltip on locked features

Stripe Setup

  • Create “Free” plan (price: $0)
  • Keep existing Pro plan
  • Set up plan downgrade flow
  • Handle trial → free conversion

Migration Plan

Existing Users

  • All current paying users → Pro (no change)
  • Trial users who converted → Pro
  • Expired trials → Prompt to choose Free or Pro

New Users

  • Sign up → Free plan
  • Show upgrade prompts naturally
  • No forced trial period

Success Metrics

  • Free → Pro conversion rate (target: 5-10%)
  • Free user retention (target: 30% MAU)
  • Time to upgrade (track funnel)
  • Feature usage by tier (identify upgrade triggers)

Questions for Adam

  1. Is 30 days enough for free tier, or should it be 7 days?
  2. Should Schedule Health Score be the main upgrade hook?
  3. Keep $5/month or adjust pricing?
  4. Add annual-only option for free tier upgrade?

Graph View