with the skill
**Present annual as a better-value commitment—but investigate month-3 churn before pushing it harder.** Otherwise, you risk turning early cancellations into annual refund requests and unhappy customers.
Your annual plan already offers a meaningful discount:
- **Monthly:** $25/month, or $300 over 12 months
- **Annual:** $240 billed yearly—equivalent to $20/month
- **Savings:** $60/year, or 20%, compared with 12 monthly payments
Here’s how I’d present and test it.
## 1. Make the comparison effortless
Show two options side by side, with annual visually emphasized:
| Monthly | Annual |
|---|---|
| **$25/month** | **$20/month, billed annually** |
| Billed monthly | **$240 billed today, then yearly** |
| Flexibility to pay month to month | Save $60 vs. 12 monthly payments |
| **Choose monthly** | **Choose annual** |
Show the rest (47 more lines)
Use a factual annual badge: **“Save 20%.”** Don’t use “Most popular” unless it’s true.
Keep the $240 charge prominent—not in a tooltip or tiny footnote. Explain renewal and cancellation terms clearly.
**Why it works:** Framing both plans in monthly equivalents makes comparison easier; showing the dollar savings makes the benefit concrete.
## 2. Sell sustained progress, not just cheaper access
People buy a habit tracker to achieve an outcome, not to purchase 12 months of software. Connect annual pricing to the long-term job they want done.
For example, above the pricing cards:
> **Build routines that last.**
> Choose monthly for flexibility, or annual for a year of habit tracking at 20% less.
If you have features such as long-term trend reports or seasonal goal planning, demonstrate them here. Don’t imply that paying annually guarantees lasting habits.
**Why it works:** Jobs-to-be-Done framing gives people a reason to want the year—not merely a reason to accept the discount.
## 3. Offer annual after a real value moment
Test an upgrade invitation after users achieve something meaningful: complete their first week, establish a routine, or review their first progress report.
Example:
> **Keep building on your progress.**
> Switch to annual for $240/year—20% less than paying monthly for 12 months.
Make any treatment of their existing monthly payment explicit.
**Why it works:** Asking after demonstrated value reduces uncertainty. It’s stronger than asking a new user to commit before they know whether the app helps.
## 4. Diagnose the month-3 drop-off
Ask departing users whether they:
- Didn’t build the habit
- Stopped finding the app useful
- Found it too expensive
- Successfully built the habit and no longer needed tracking
Those require different solutions. **Annual billing changes payment timing; it doesn’t necessarily improve retention or customer outcomes.**
## What to test first
Start with the transparent pricing comparison above, then test the value-moment upgrade prompt separately.
Measure **annual selection and revenue per visitor**, alongside refunds, chargebacks, and 90-day engagement. Don’t declare success just because fewer customers can cancel their payments by month 3.