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How To Encourage Users To Upgrade From Monthly To Annual Subscriptions

Guide users through upgrading to annual in the app and use Start Here content and promotions to drive conversions and improve retention.

Written by Jordan Blake

Why Promote Annual Upgrades?

Encouraging monthly users to switch to annual:

  • Increases overall retention and reduces churn

  • Locks in committed, long-term supporters

  • Gives you more predictable, upfront revenue

  • Lets you offer promotional pricing and incentives to drive conversions

How Users Can Upgrade To Annual In The App

You should guide your users through the following steps. The process is the same on both iOS and Android.

Step 1: Open the App

Open the Playbook app on their device.

Step 2: Tap Their Profile

Tap their name on the bottom right corner to go to their Profile.

Step 3: Tap "Manage"

Tap “Manage” next to “My Subscriptions.”

Step 4: Tap "Upgrade to Annual"

Select the “Upgrade to Annual” option.

Step 5: Enter Discount Code (Optional)

Users can enter a discount code if you've provided one.

Step 6: Confirm and Upgrade

Tap OK to confirm. Their card on file will be charged, and their new annual billing cycle will begin immediately.

In addition to the Profile → Manage path above, monthly subscribers will also see an "UPGRADE TO ANNUAL" banner they can tap on directly inside their workout experience — for example, inside a program or challenge they're actively working through — to accomplish the same goal. This banner appears automatically if a user is a paying monthly subscriber to your channel.

Use Your Start Here Category To Promote Annual Upgrades

We recommend using your Start Here category to explain the value of switching to annual. This category is often the first place new users visit and is a great opportunity to encourage upgrades early on.

You can add content in two formats:

  • Record a video of yourself explaining the benefits of annual (savings, commitment, long-term results)

  • Upload a visual tutorial with screenshots showing where to go:
    Profile → Manage → Upgrade to Annual

Make sure to clearly outline:

  • Where users can find the upgrade option

  • How much they’ll save by switching

  • Any limited-time discount code you're offering

  • Why annual helps them stay accountable and consistent

Tips For Getting Users To Upgrade

Highlight Long-Term Savings

Let users know that upgrading to an annual subscription will save them money over time compared to monthly payments.

Example: “Save over 30% by upgrading to an annual plan today.”

Offer Exclusive Discounts

Use Playbook’s discount code feature to offer promotions tied to:

  • New product launches

  • Seasonal campaigns

  • Loyalty rewards

You can create and manage discount codes in your Creator Dashboard under Promotions.

Use Expiration Dates To Create Urgency

Limited-time discounts drive action. Encourage urgency by stating when the offer expires.

Example: “Get 25% off annual — offer ends Sunday at midnight.”

Promote Through In-App Messaging

Use Playbook’s in-app messaging tool to send direct messages to your monthly subscribers. Share upgrade benefits and any discount code you're offering.

FAQs

Will The User Be Charged Immediately?

Yes. When a user upgrades to annual, their stored payment method is charged immediately for the prorated amount. Their billing cycle renews 12 months later.

Can Creators Force Or Trigger The Upgrade?

No. Only users can upgrade their subscription. However, you can guide them through the process and use messaging and Start Here content to encourage it.

Does This Impact Creator Revenue?

Yes. Annual plans lead to larger upfront payouts and stronger retention. As with monthly subscriptions, creators earn 80% of the net revenue after fees.

What if the user forgets to add a discount code during the upgrade process?

If a user forgets to add a discount code during the upgrade process, please have the user reach out to [email protected] for further assistance.

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