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Make More Money with Better Upgrade Emails

If you run a SaaS business, then at one point or another, you must ask people to give you money. The Upgrade email is a little virtual memo that reminds your users how awesome your product is and convinces them to become customers.

The challenge is that upgrade emails don’t fit all business models, and when they do, people often fail to optimize them for the best results.

In this piece, I want to cover when and why you should use an upgrade email, when is the best time to send the upgrade email, and how the greatest software companies write upgrade emails to make more 💰💰💰.

Let’s jump right into it!

Do Upgrade emails work?

Upgrade emails are a powerful conversion tool, but even the sharpest knife can’t help you in a gunfight. Go ahead and build the smartest, most hyper-personalized, timely upgrade email — it still won’t make much of a difference if your business doesn’t satisfy a few critical conditions:

1. Great (or decent) product

Upgrade emails can’t unsuck your product or product messaging. Your software must solve a credible need and have at least a partial product/market fit. I’ve written the most thorough piece on validating SaaS ideas on the interwebs, head over there now if you’re that early in your SaaS life.

If people are struggling to understand what your tool does, go back to improving the top stages of your marketing funnel, and don’t worry about upgrade

You must get this right before a user is ready to upgrade and start a subscription, there’s no way around it.

2. People experience value in your product

If your onboarding process is a boxing match, think of the upgrade email as the final blow. It’s the finishing stroke, the end of the road.

The goal of the upgrade email is to close the sale by neutralizing any lingering objections. Not to onboard the person or educate them about your tool.

Therefore asking people to upgrade when they haven’t reached any Aha moments or experienced at least a trickle of value is going to be like asking a stranger on the street to marry you — awkward and probably annoying.

The whole purpose of the free trial window is to get people hooked on your product. Only then it makes sense to ask them for money.

3. A self-serve business model

In a product-led business, users can self-serve in your app and achieve their desired outcome without relying on a sales or customer success representative.

In that model, your upgrade email actually plays the role of a salesperson — a persistent closer that works day and night to close more deals. Its job is to emphasize the value of your product, counteract objections, and convince the user to upgrade.

However, the upgrade email is often ineffective or straight-up useless in a human-driven, high-touch business model.

Let’s face it. It’s naive to expect that an email will close the sale in a high-touch onboarding process:

  • You don’t get many trials.
  • Your product requires a lot of upfront knowledge.
  • It has a complex setup.
  • It just takes a lot of time to start to deliver value.

In that case, you need a human-assisted closing process with personal sales calls and well-thought-out closing logistics. It’s still worth having an upgrade email that reminds users how to become paying customers but don’t expect that an email will seal the deal.

Further reading: Product-led Vs. Sales-led Onboarding: Which one should you choose?

4. A trial that works without a credit card

There are two types of SaaS trials: trials without a credit card (people can sign up and try your tool without their credit card details) and trials with a credit card where people leave the card details upfront.

The Upgrade email is irrelevant in the latter case, as the billing system will automatically begin charging (i.e., upgrade) customers when the trial ends.

This second approach has a completely different set of challenges like: you need to offer a 14/30-day money-back guarantee and notify users ahead of time that they’ll get charged in order to avoid chargebacks and refunds. We’re not going to cover this approach here.

When is the best time to send the Upgrade email?

The Upgrade email is usually created as a part of the trial expiration email sequence. Most SaaS companies send the upgrade email as a trial expiration notice towards the end of the onboarding or when the trial ends.

I propose a different, more effective approach:

Send Upgrade emails based on your user behavior. That way, the upgrade email will be in pace with the customer journey and would map to the value they’ve experienced with your product.

Here’s the flow I recommend:

  1. If the user has reached most or all of the critical value moments before the trial ends → Send Upgrade Email.
  2. If the user has experienced value and trial ends soon → Send a Trial Expiration Email with a prompt to upgrade.
  3. If the user hasn’t experienced value yet and the trial ends soon → Send a Trial Expiration Email with an extension option.
  4. If the trial has ended, and the user hasn’t converted → Send feedback survey email.

In other words, you can send the Upgrade email when the trial ends or sooner if the value for the user is already in place — a combination of time-based and behavior-driven triggers.

How to make а good Upgrade email great?

1. Quantify the value of the trial

Apart from including the user’s name, you can add any relevant information that pertains to the trial. For instance, tasks completed, documents created, members added, hours saved, bugs resolved, and so on. This is an easy way to quantify the value that the user has experienced throughout the trial.

In the example below, Zapier shows the number of tasks you have automated since you started using the platform.

Zapier upgrade email


2. Emphasize what the user misses when not upgrading

“I like to win, but more than anything, I can’t stand this idea of losing. Because to me, losing means death.” — Lance Armstrong.

Demonstrated by Amos Tversky and Daniel Kahneman in 1992, the key idea behind the loss-aversion bias is that for people, the pain of losing something is twice as powerful as the pleasure of gaining the same thing.

The upgrade email is a convenient place to put this bias into practice. You can list the features and the benefits that your users are going to miss if they fail to upgrade.

Pipedrive uses loss aversion to alert users that they no longer would be able to see their data or progress.

Pipedrive trial expiration email

3. Provide pricing details and upgrade instructions

Include your pricing plan details or a link to your pricing page. Explain what people need to do to upgrade and avoid any interruptions with their service.

In the email below, Format includes a link to their pricing plans along with clear upgrade instructions. Notice the  “reactivation” call to action that ties in the loss-aversion bias.

Format account deactivated email

If you have a complex pricing structure (metered pricing, credits, quarterly plans, etc.), make sure you explain what exactly the user pays for when becoming a subscriber.

Reference check platform Veremark does a good job of explaining their credit system in the upgrade email:

Veremark credit details email

4. Share you contact information

Upgrading is a big decision. Make it easy for people to get in touch with you. Show that you’re there to help, explain the pricing, or answer any questions.

HelpScout trial expiration email

5. Handle any remaining objections

Sales resistance could be generally broken down into  4 groups:

  1. Price/Risk — your product is too expensive or doesn’t deliver the required ROI.
  2. Quality of Service — missing features, irresponsive support, lack of documentation, and so on.
  3. Trust — the credibility of your small startup.
  4. Stall — cold feet towards the end of the sale due to remaining conflicts or lack of urgency.

Use your post-trial survey email and feedback from sales conversations to figure out the most common objections in your trial.

Let’s say that “software complexity” is one of your primary customer objections. In that case, you might want to mention your superior customer success department, complete knowledge base, and active community.

See how ActiveCampaign handles that in their upgrade email, cleverly positioned just below the CTA:

ActiveCampaign trial expiration email

6. Give your users options

Don’t be a jerk, give people options. See how Basecamp asks you if you need some extra time or prefer to cancel instead. This is much friendlier than the typical threat of blocking your account and removing any of your existing data.

Basecamp upgrade email

7. Nail down the email with a clear CTA

Keep it simple. Again, the goal of your upgrade email is to convert free users to paying customers, not to educate, teach, or onboard people. Make sure to follow the formula for simple emails:

1 Email = 1 Business Goal  = 1 Desired Outcome = 1 Call to Action

Note how the emails below use a clear, single CTA that’s easy to spot. The button color is always vivid, and there’s no competition for the email’s focal point.

your apple music membership

Evernote upgrade email

8. Create a sense of urgency

“Urgency means something is urgent, it needs to be dealt with as soon as possible.


Sense of urgency means you always see things urgent.

Meaning you don’t really wait for a situation when you are asked to deal with the situation urgently.” — Source

You don’t have to wait for the end of the trial period to create urgency. Instead, identify the most engaged users (i.e., the ones that have experienced value) and build some urgency before that — these are the people that are most likely on the fence to convert.

One of the easiest ways is to offer a limited discount for your tool (examples below). This seems to be a common tactic among B2C tools and mobile apps.

That said, discounts won’t be my first choice when it comes to B2B SaaS, as they devalue your product. A more sound approach, in that case, would be to offer some extra usage or a premium feature for free.

Grammarly trial email with discount
Podia discount trial email

9. Use social proof to convince users

Testimonials, case studies, and examples from current customers — all things that you can include in the upgrade email to persuade users to upgrade today.

In the email below, Podia shares some of their exciting case studies, while in the second email Squarespace uses visual examples to show beautiful customer websites.

Podia social proof trial email
Squarespace trial email

The most effective email templates you can steal for your SaaS

All right, we explored some of the best Upgrade emails used in the SaaS world. Now I’ll share with you a few editable templates that you can copy and paste (with a few changes) in your marketing automation tool.

1. Trial limit reached upgrade email template

Subject line: No more [your value metric – credits / space / searches]!

Body copy:

0  [your value metric – Credits / Space / Searches] Left

You used all of your free credits at [product], well done!

By now, you should have a good idea of all that [Product] has to offer. So it’s time to make that critical decision to…

[Upgrade for more credits CTA]

[Explain your value metric]

Credits are used to [find leads / send checking requests / do more searches].

[Explain how to make a purchase]

You can purchase these within the Credits tab in “settings”.

[Explain any bulk discounts if it’s a metered system]

Credits can be bought in bundles, the bigger the package — the lower the cost of each credit so the more cost-effective each [lead / check / search] becomes.

[Upgrade for more credits CTA]


Co-founder of [Product].

2. Value experienced upgrade template

Subject line: [XXX] of [tasks / searches / lead] [created / made / found]!

Body copy:

Hey [Name]

[Demonstrate usage]

Since you started using [Product] you’ve [automated / made / found] [XXX] [tasks / searches / leads].

[Quantify the benefit]

This means you have managed to [address the primary outcome] save at least 10 hours of manual work / increased traffic / resolve a bug.

Your free month to try [Product] has reached the end, but you can still [mention benefit again] save time automating tasks when you subscribe to a paid plan.

[Upgrade CTA — Keep your tasks running]

You also get:

  • [Premium feature 1] that helps you with [benefit 1].
  • [Premium feature 2] that helps you with [benefit 2].
  • [Premium feature 3] that helps you with [benefit 3].

[Recommend the best plan based on their usage]

Based on your usage over the past two weeks, you should try the Basic plan — it’s a great place to start.

[Upgrade CTA — Keep your tasks running]

3. Sticky premium feature upgrade template

Subject line: How to use [sticky premium feature]

Body copy:

If you’re a [sales person / designer / developer / your customer persona], you probably know that [explain their biggest pain-point: “hardest part in sales is not selling to the decision-makers but finding them in the first place!”]

Imagine [picture the perfect future for the user: “how many more deals you could close if you were always talking to the right person in charge”]

Click on the video below to learn how to [step they need to complete in your product to start using the most valuable feature and achieve that perfect future. Use the video to demonstrate a premium feature and get people to upgrade their trial.]

[Video or GIF demonstrating where in the your app users can activate this feature]

[Mention how they can upgrade to get access to a premium feature]

[Upgrade Now to Get the Best Benefits Button]

[Offer help]

P.s. To get help with [sticky premium feature] reach out to us by replying to this email or joining us on:



Our Mastermind group


[Your name]

4. Universal trial over template

Subject line: Your [Product] account will expire in 24 hours

Body copy:

Hey John,

Your [Product] trial expires in 24 hours.

Your account will be deactivated in 24 hours, and all of your [tasks/flows/messages] will be disabled.

You’re also going to lose access to any data you have in [Product] – [list what they’ll lose: tasks, flows, data, emails]. You no longer will be able to [experience specific benefit].

Do not worry! We keep it safe with us for when you decide to upgrade.

Our plans start at [price], and by upgrading now, you will ensure your marketing automation flows stay active.

[Mention the benefit]

Convert more leads, retain more customers, and grow your revenue with robust marketing automation flows.

[CTA — Upgrade your account]

5. Upgrade email with options template

Subject line: Upgrade now to keep using [Product]

Body copy:

Hi John,

Your [Prodocut] trial has expired, and your account is now frozen, so you and your team members can’t access it. To pick up where you left off, just the button below and upgrade now.

[Upgrade now to keep using [Product]]

  • [Address objection 1 — Upgrading only takes a minute]
  • [Address objection 2 — Everything you created during your trial is still safe and sound].
  • [Address objection 3 — Keep in mind we don’t hand you the tool and walk away. We are here to help you get the most of [Product]]

[Option to extend trial]

Need extra time on your trial?

Just reply to this email or contact our support team [link to support]. We’ll get right back to you in a few minutes.

Not ready to upgrade?

No problem. We’re going to downgrade you to a free plan. You can either do nothing, and we’ll downgrade your account, or you can downgrade here.

Upgrade emails further reading

4.8/5 from 228 reviews
4.9/5 from 158 reviews
4.9/5 from 155 reviews
4.91/5 from 154 reviews

Meet your new marketing automation platform

Customer messaging tools don’t automate workflows outside your product and marketing automation tools are bad at behavior emails. Encharge is the best of both worlds — a marketing automation platform built specifically for B2B SaaS businesses

“Encharge helped us visually redesign our onboarding flow resulting in a 10% increase in our trial activation rate."

Camille Richon
Founder Payfacile
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