Switching from Monthly to Annual: 10+ Email Examples to Promote Yearly Plans

Annual billing is a win-win for both parties: you improve your cash flow and increase retention, while your users save money in the long term.

Since it’s a big ask, how do you ask customers to switch without sounding pushy or desperate?

In this post, we’ll talk about the pros and cons of asking users to switch, when you should send that first email, and how other SaaS companies are doing this.

Why should you ask users to switch from monthly to annual billing?

Offering both monthly and annual plans can boost your growth in many aspects. While annual billing is usually the default for enterprise deals, should you ask smaller customers to make the switch?

Let’s consider the pros and cons of promoting annual billing options.

How it helps your business

• Boosts customer retention. Switching to annual billing keeps users around long enough to experience improvements and new features. This makes it more likely that they’ll renew the following year.
• Immediate increase in cash flow. Getting paid upfront covers business expenses and funds investments (i.e. marketing activities), which can help increase your profit in the long term.

What to watch out for

• MRR might drop in the short term. Annual billings are usually cheaper than your monthly rate x 12, so keep in mind that your MRR (and consequently your ARR) might go down in the short term.
• Potentially causes churn. If you charge based on usage, the next bill may be surprisingly big for your customers and cause them to churn (at Userlist, we even considered removing annual plans altogether for this reason — note from Jane).

Different ways to ask users to switch to annual billing

You can ask users to upgrade using different formats:

• Dedicated upgrade email
• Section in a newsletter
• Seasonal promotion that includes an annual deal
• In-app notification (sure, we’re talking about emails here, but don’t forget that you can do this right inside your product)

Best practices for annual billing upgrade emails

Focus on the benefits of switching

Since you’re asking customers to pay a relatively big amount upfront, tell them what’s in it for them.

Most emails highlight the amount saved, but it’s not just about money. Other benefits and perks may convince them to make the switch.

Be clear and specific about the details

To avoid confusion and friction, be clear and specific about important details such as:

• The deadline (if it’s a limited time offer)
• Who can claim the offer (i.e. if it’s only limited to a certain region)
• Terms and conditions of the offer
• Steps on how the user can make the switch

Do the first ask immediately

New users are still enthusiastic about making the most out of your product, so take this opportunity to make that first ask.

But if you’re waiting on them to upgrade from free to paid before asking, Marc Thomas of Positive Human advises to send the email about 30-90 days after the first upgrade.

Don’t just ask once

If you’re planning an email sequence for this campaign, Marc says to schedule emails every 50 days so your emails land at different times of the year that might coincide with crucial periods (i.e. budget reviews).

You can also send the same email to users by setting up a repeat cycle until they make the switch to annual billing.

Send a reminder when credit card is about to expire

Because of the long interval between billing cycles, credit cards might expire during this period.

To avoid friction on renewal, remind users to update their credit card details at least 30 days before the current one expires.

Monthly-to-annual upgrade email examples

#1. Anthropic (Claude)

For one of their newsletters, Anthropic included a dedicated section to promote their new Claude Pro annual plan for US-based customers.

To emphasize how much users can save, they show how much the annual plan costs and how this is cheaper per month versus the monthly plan. Anthropic also included a CTA text that takes users to an upgrade page.

#2. Livestorm

Subject: Back-to-Work Offer: Get 3 Months Free On a Yearly Plan 💼

Livestorm offered this special promo during the back-to-work season. While they’re essentially the same, stating “free 3 months” is more enticing compared to “discounted”.

Formatting the promo details in bold makes it easier for readers to get the gist of the email. They then show the breakdown of how much the reader can save when switching to annual and when the offer expires. Livestorm also wrote down the specific step on how users can make the switch.

Meanwhile, here’s what they sent to new customers.

Subject: Livestorm Special offer: Get 3 months free for a yearly plan

Similar to the previous email, Livestorm uses the phrase “3 months free” to talk about the special offer. They also give clear instructions on how the user can make the switch.

#3. Restream

Subject: 🎃 31% Off screaming - er, streaming. An Out-of-This-World Deal!

As part of their Halloween promo, Restream sent this email to encourage the reader to return to a paid plan and upgrade to annual billing.

Aside from the discounted offer, they also highlight the premium features the user can get access to when they upgrade. Restream creates a sense of urgency by including the deadline for the offer.

What can be done better?

There should be another CTA button/text at the end so the reader won’t have to scroll back up to claim the offer.

#4. Riverside

Subject: Final Day: Get 50% Off - Riverside.fm

Riverside did this for one of their Black Friday offers, highlighting the big discount the user can claim by repeating “50%” throughout the email. They enumerated the steps on how to claim the offer before ending the email with a CTA button.

#5. Snippet

Subject: Become a Snippet PRO

As part of their general upgrade email, Snippet highlighted that for a limited time, the user can get two months free if they go with a yearly plan. They also showcase a few features that users can maximize on a paid plan.

#6. Calendly

Subject: Two free months of Calendly?

Calendly also uses “free X months” to encourage users to switch to annual billing. They include steps on how to claim the offer and also link to the billing page.

In the P.S. section, they reassure the reader that the Premium service will keep running normally should they want to skip on the offer and stay on the monthly plan.

#7. Zapier

Subject: Pro Tip: Add a free month of Zapier to your subscription

Zapier also used the term “free” for their special offer to pique the reader’s interest. They have a dedicated section discussing the benefits they’ll get by switching which are:

• A free month of the premium plan
• Enjoy the automation power
• User will only deal with one invoice each year

The email ends with a clear “Switch to Annual Billing” CTA.

#8. Freepik

For their email, Freepik creates FOMO by saying that this is an exclusive offer and highlights the benefits of switching to an annual plan. Their email ends with a CTA button and other important details in claiming the offer.

What can be done better?

• The deadline, instructions, and promo code should come before the CTA so the reader doesn’t miss it.
• The CTA text on the button should be “Get -40% on annual” so it’s clear even when the reader is just skimming the email.

#9. Skillshare

Subject: Save Big with Premium Membership

Unlike the other examples in this list, this email from Skillshare focuses on the perks that annual members enjoy, showing some of the popular platforms they have partnered with. The email ends with a button to upgrade, followed by the terms and conditions of the perks.

Here’s another promo they ran a few weeks later.

Subject: Surprise: Save 30% on Premium Membership

This one focuses on a limited time discounted offer for their annual plan, highlighting a few benefits the user can enjoy when they upgrade. The CTA button is followed by important terms and conditions for the offer.

#10. Feature Upvote

Thanks to Steve McLeod for sharing this example.

Subject: Save 2 months on your Feature Upvote subscription

Feature Upvote went with a plain text email format, making it seem like a personal email from the team to the user.

To encourage the user to switch to yearly billing, Feature Upvote tells the user that they want to help them save money and reduce the amount of paperwork. They enumerate the steps on how to make the switch, and include a CTA text redirecting to the billing page.

#11. VidAngel

Subject: In case you missed it: Meet our new annual plan

To promote their new annual plan, VidAngel packaged it as “a presidential plan for a presidential service”. To further highlight the $20 savings, they injected a bit of humor by highlighting a few things the user can buy with the $20.

The next section highlights a few customer testimonials, which ends with another CTA. They stick with the presidential theme of the email by suggesting political TV shows and movies the user can watch with their platform.

What can be done better?

“GET STARTED NOW” is a generic CTA and it might seem like the reader will be signing up for a new account. It’s better to use CTAs like “Switch to Annual” as the first CTA so it’s clearer.

Switch to annual billing email template

Start asking users to make the switch with this email template.

Subject: $X worth of free [product]

Turn monthly plans into annual commitments

Annual upgrade emails don’t have to sound pushy. Highlight the value your customer is getting when they switch – whether that’s cost savings, reduced paperwork, or other perks.

Even a 10-20% conversion significantly impacts your business growth.

Check out other articles on pricing and billing:

• How to Write a Pricing Update Email: 15+ Examples from Real SaaS Companies
• 10+ Best Subscription Renewal Emails (Annual Payment Reminders)
• Discounts & Promotions in SaaS Email Marketing: 15+ Email Examples
• How to Unlock SaaS Growth with Referral Emails: 10+ Examples (Free Template Included)