How to Write Upgrade Emails That Convert with Live Examples

Your upgrade emails can get messy if you don’t apply the right strategies. This article provides insights into how to create great upgrade emails that convert.

How to Write Upgrade Emails That Convert with Live Examples

People are signing up for your free trials. They see your product as a viable solution to their problems. They may become qualified users who experience value from your product. They may even be the ideal persona for a paying customer.

But there’s a problem — some of them lose interest in your software. This means that they don’t engage with your upgrade emails. Some click the “upgrade” button in your emails but fail to finalize the payment process. They simply become — non-converting users.

These are examples of some of the major challenges most SaaS marketers and founders deal with — creating upgrade emails that persuade trialists to convert to paying customers. The good thing is that all hope is not lost.

In this article, we’ll show you how to prevent trial users from slipping through the cracks. You’ll learn how to create upgrade emails that convert prospects to paying customers.

Before we begin, we must lay the groundwork first. Let’s address an important factor that must be considered before creating upgrade emails.

Table of content

  1. When’s the best time to send upgrade emails?
  2. Consider user segment and behavior
  3. Best practices for creating upgrade emails
  4. Getting started on upgrade emails

When’s the best time to send upgrade emails?

For your emails to have a positive impact on trialists, they must be sent at the right time:

  • When you’ve convincingly moved a prospect through the 5 primary stages of awareness.
  • When prospects become active users, this shows that trust and value are already in place.

Consider user segment and behavior

Your upgrade emails should be delivered based on how users interact with your product. Just because someone signed up for your product doesn't mean that they are ready to buy. This is why you must create user segments when crafting upgrade emails. Typical trial user segments include:

  • Qualified users that have a problem, but don’t see you as a solution due to various reasons.
  • Users that have the problem see you as a viable solution, but they haven’t experienced value, yet. “No aha moment”.
  • Qualified users that have gained value with your product features within the trial window.
  • Unengaged users that sign up but never use your product simply because — life happens, people are busy and can be easily distracted.
  • Unqualified users are people you don’t want as customers because they are most likely to churn. It could be that they signed up because your plan is free.
  • Non-converting users due to various pricing and sales objections.

When you create upgrade emails without considering user behavior and segments, you could send a disconnected, irrelevant email with phrases like “we hope you have enjoyed using our tool”, and “you’ll fall in love with our product features”.

This doesn’t mean that these phrases are terrible. They may be applicable if they are used for a trial user segment that has gained value with your product features within the trial period. So, if they are interested, you only need to remind them that their trial is almost over. A brief upgrade email with a compelling subject line and call to action should do the work.

Unfortunately, this doesn’t happen all the time. This is why onboarding emails are important to remind users of your product, address objections and nudge them back to using your product. You need to qualify prospects and consider the real user journey when you create your upgrade emails.

Let's go through some of the best practices for creating upgrade emails and how they apply to each user segment.

Best practices for creating upgrade emails

1. Track feature usage & user behavior

If you don’t track feature usage and user behavior, then you could end up sending upgrade emails that aren’t personalized and compelling. When you track feature usage and user behavior, you lay the foundation for applying some of the tactics explained on this list.

This helps you connect with users on a personalized level and figure out ways to deliver relevant messages throughout your upgrade email sequence.

So, start collecting this data as soon as possible. With a good marketing automation tool like Engage, you can track metrics such as:

  • The number of logins.
  • Most used features.
  • Last time active on the app.
  • Usage of metered features.

When you track these metrics, you’ll be able to apply some of the following tactics.

2. Highlight the value of the trial

Remember the user segments we mentioned earlier? This strategy is ideal for users under the segment “qualified users that have experienced value with your product within the trial period.” When you track your app user behavior, you’ll be able to identify some activities that show that they are deriving value from your product.

This data can be used to personalize your upgrade email for improved conversion. For example,  milestones achieved, hours saved, and the number of members added. Take a look at an upgrade email from Zapier:

Zapier: An example of using data to show derived value in an upgrade email for improved conversion. (Source)

In this email,

  • The user automated 229 tasks.
  • It also applies loss aversion by highlighting the relevant features the user will lose access to. (more on this in the next strategy)

This example shows that the user has derived value from Zapier and must upgrade to have continued access to key features.

3. Highlight features/benefits the user will lose when they don’t upgrade

Another way you can motivate users to upgrade is by highlighting the key features and benefits that they will lose if they don’t upgrade. This strategy applies loss aversion — which is the fear of losing something valuable.

Back to Zapier’s upgrade email mentioned above. This example highlighted relevant features the prospect will lose access to if they don’t upgrade — multi-step zaps and premium apps. Users will most likely convert when they are reminded that they may lose something that they already have.

This strategy is more effective for qualified users on trial with premium features. This way, they already have a sense of ownership that they won’t want to lose.

3. Use social proof to persuade

A trial user may gain value with your product features but may hesitate to hit the upgrade button. It could be that they aren’t fully convinced that your product is ideal and trustworthy.

You can address this issue by providing social proof in your upgrade emails. Don’t just state that thousands of customers have enjoyed using our software. Instead, be specific. State how an active upgraded user has successfully used key product features. This can signal to users that they can also be in a similar successful situation if they upgrade to become paying customers.

4. Provide a clear call to action

The goal of your upgrade email is to get your trial users to upgrade before their trial expires. Your call to action should clearly state that. Don’t beat around the bush. Avoid trying to get users to do certain things like check out the latest product upgrade, read a blog post, listen to a podcast, etc. Ensure you provide necessary information on how users can upgrade.

Squarespace: An example of providing the necessary information on how users can upgrade.(Source)

5. Address prospects' objections

A user can explore your product features, use the most relevant features, achieve successful milestones and be willing to pay 5x your product pricing. If you don’t address the barriers standing between these users and the upgrade button, they become non-converting and you may lose them.

Rather than hope that things will work out fine or desperately offer a discount (offering a discount to a user that hasn't gained value with your product feature isn’t effective). You need to find out what’s going on in your users’ minds.

With customer data and interviews, you can analyze key user behavior and identify the things that are preventing prospects from converting. Many things could prevent a user from converting. Some of them include:

  • Unable to reach certain success milestones despite consistent logins.
  • Unable to reach a consensus among major stakeholders.
  • Overwhelmed by the complexity of your product features.

When you obtain customer data, you can send upgrade emails to the non-converting user segment, addressing their objections. For example, if you find out that a user is overwhelmed by the complexity of your product, you can send an upgrade email that offers support like tips and tutorials, walkthrough videos, help documents, user community, etc.

Copper: An example of an upgrade email that offers support like tips and tutorials.(Source)

Getting started on upgrade emails

It’s possible to create upgrade emails that convert, but you need to apply the best tactics for a higher chance to be successful. Don’t rely on hope or offer unnecessary discounts when trying to get trialists to convert.

Many barriers could prevent prospects from hitting the “upgrade” button. So, you must analyze customer data and conduct interviews. This will help you to focus on the right user segments and deliver more personalized and relevant upgrade emails. Focus on providing value first, address prospects’ objections, and most importantly — send upgrade emails at the right time.

At Engage, we help businesses track customer preferences, properties, events, and actions so they can create customer segments and send automated personalized messages and upgrade emails that foster growth and retention. Sign up now.