If you’re building a SaaS product, upgrade emails are one of the most effective tools to turn free users into paying customers.

But what makes an upgrade email actually work—and when should you send it? In this guide, I’ll walk you through how to write upgrade emails that feel helpful, timely, and drive real conversions.

Here’s what we’ll cover:

• What makes an upgrade email successful
• When to send upgrade nudges (especially to trial users)
• Real-life examples from 13 top SaaS companies
• What to include—and what to avoid

Ready to level up your upgrade flow? Let’s dive in.

Why upgrade emails are a SaaS growth engine

For any SaaS business with a free plan or trial users, upgrade emails are a direct path to increasing revenue—without chasing new leads. These emails help convert free users who already know your app into paying customers by showing them the benefit of sticking around.

You’re not just reminding someone to upgrade—you’re guiding them to get more value out of what they’ve already started. Whether your product helps people manage their time, create better documents, or analyze their data, the upgrade email bridges the gap between free exploration and long-term commitment.

It’s not about pressure. It’s about timing, clarity, and support. When you get that right, you’ll see how well upgrade emails work to convert the right users at the right moment.

What makes upgrade emails work?

A good upgrade email doesn’t just ask users to purchase—it shows them why upgrading makes sense right now. The most effective ones clearly explain the progress someone has made and what they’ll unlock on a paid plan.

You’ll want to highlight real benefits, not just features. Think improved access, more tools, or the ability to create without limits. Don’t forget a direct link to upgrade—make it easy to take action.

Also, address the common blockers: worry about cost, confusion about what changes, or uncertainty about the deal. If you can include social proof or a clear example of what paying customers get, even better.

And yes—keep it human. You’re not a computer, you’re a person talking to another person. Make your email sound like it.

How to personalize your upgrade email

The more relevant your message, the more likely it is to land. That’s why personalization is key—especially in a world where users are bombarded with spam and forgettable promos.

💡 Use usage and log data to tailor your message. If someone has created several files, or checked out your templates, mention it. Personalize by name, of course, but go deeper—talk about what they’ve done, what’s left to complete, and what they’d gain with a paid account.

You might say something like, “You’ve used 80% of your free plan—here’s what happens if you upgrade today.”

These small touches help convert trial users who are close to the finish line. They show you're not just sending a mass course of emails, but actually paying attention.

When to nudge trial users

The timing of your upgrade email can make all the difference. For trial users, the days right before their trial ends are key—but it’s not the only window.

You can send reminders when someone’s progress stalls, when they unlock a key feature, or when they hit a limit on their free plan. That “you’re almost there” moment is a great time to convince them to upgrade.

Another option: offer a little extra time if they haven’t made a decision yet. It gives space to decide, without rushing. You can also invite feedback or offer support if they’re stuck.

And remember—some users might just need a gentle note that their account is about to expire. Others may prefer a strong value pitch. Pay attention to your user behavior and test to find what gets the best results.

13 examples from top SaaS companies

Pipedrive

This is a strong example of a clean, benefit-focused upgrade email for trial users. The headline clearly states the trial has expired, which creates urgency, but the tone stays calm and helpful. I like how they offer a link to “Keep my account,” making it easy to act.

The follow-up section highlights four key CRM features—clear value that helps convert free users by showing what they’ll miss. It’s also smart to mention data deletion after 60 days. That little detail adds a subtle push to upgrade today without sounding alarmist.

Loom

Loom takes a no-nonsense approach to the trial expired moment. They clearly show the shift to the free plan and contrast it with what’s been lost—like branding, engagement insights, and shared library access.

It’s a smart way to let users feel the downgrade. The CTA is clear, and the message focuses on helping users continue without missing a beat.

Calendly

This upgrade email strikes a friendly, confident tone with a simple ask: upgrade today to keep the features you're already using. It’s great for trial users—reminding them of the benefits they’ll lose without sounding alarmist.

Clear feature blocks help reinforce value, and the layout makes it easy to decide or compare plans with just one click.

Unlike most upgrade emails in this article, this one targets paying customers, offering a deal to switch to annual billing. The message is simple and benefit-first: save 20%—that’s nearly 3 months free.

There’s no long list of features or urgency pressure, just a clean offer and a single CTA. For active users already seeing value, it’s a smooth conversion nudge.

Notion

This upgrade email is usage-triggered and well-timed. After hitting the limits of site customization, Notion follows up with a clean message that shows what’s just out of reach—custom domains, branding, and Google Analytics.

It doesn’t overwhelm; it simply highlights value. A subtle nudge like this, tied to feature-based friction, is a great way to convert free users who are already engaged.

Zapier

This is a classic countdown email for trial users, and it works. “Your trial ends in 3 days” sets a clear deadline. The messaging is short but informative—users know what’s at stake if they downgrade to the free plan.

The email also links to helpful resources, which adds support and education instead of just pushing for the upgrade.

Semrush

This one's a confident follow-up before the trial ends, focused on what’s about to unlock with a paid account (this is an "opt-out" trial, CC required).

It’s less about convincing and more about reinforcing the benefits: full tool access, reports, community, and an account manager. It also reminds users they’ll lose all that if they cancel. It’s clear, upbeat, and progress-focused.

DocuSign

DocuSign’s email leans into the idea of doing more—not just avoiding a downgrade. It’s a great example of a benefit-driven upgrade email, emphasizing custom branding and freedom from monthly send limits.

They also offer a webinar as a helpful next step, which adds support and a softer conversion path. It’s well-balanced, especially for thoughtful users who need time to decide.

Freepik

This upgrade email targets existing users with a bold annual plan offer—40% off. The design grabs attention instantly, and the copy emphasizes both creative freedom and priority support.

The call to action is clear, and the discount feels time-sensitive without pressure. It’s a smart play to convert monthly or free users who are ready to commit long-term.

Grammarly

This email highlights a new integration—Grammarly in Google Docs—and uses that as a launchpad to promote Premium. It’s a great move to educate and subtly convert users who are already active.

The visuals are clean, and the copy emphasizes real benefits, like tone detection and writing suggestions. A simple CTA invites the next step without pressure.

Hunter

Hunter keeps it simple: you’ve hit your usage limit, and here’s how to get more. This isn’t a trial reminder—it’s a smart trigger for free users bumping against a cap.

The message gives just enough detail and opens the door to contact the team for guidance. Clean, helpful, and conversion-minded without feeling pushy.

Google Workspace

This email delivers pure utility—each section stacks a clear benefit: more storage, smarter AI, easier sign-offs, and tighter security. It’s a textbook upgrade pitch for a growing SaaS business.

Visually clear and copy-rich, it speaks directly to people who’ve hit the limits of the free plan and are ready to upgrade their account for real team progress.

Phantom Buster

This one's fun and refreshingly non-pushy. “3 days, and it’s over.. or maybe not?” grabs attention without pressure. Instead of jumping straight to the upgrade, they offer value first—three use cases you can still explore.

It’s a clever mix of education, encouragement, and support that lets trial users feel progress before they commit to a paid plan.

Claude

This email doesn’t just push an upgrade—it introduces a compelling product milestone. By showcasing the new Claude 3.7 Sonnet and tying it to the Pro plan, it speaks directly to power users.

The added bonus? A GitHub integration that hints at deeper workflow potential. This is a great example of feature-led messaging that nudges users to upgrade today.

Common mistakes in upgrade emails

💡 One of the biggest mistakes? Sounding too pushy or desperate. Nobody likes an aggressive nudge. Another one: skipping personalization or sending irrelevant offers. If your trial users or free users can’t see how the upgrade improves their specific use case, they’ll ignore it.

Lastly, avoid overwhelming design or content—emails that try to say everything often end up saying nothing. Clarity, timing, and value are key.

What to include in your upgrade email

Start strong: make your value proposition instantly clear. Highlight what they’ll gain—features, tools, or support they won’t get on the free plan. Add a clear CTA (think “Upgrade today” or “Choose your paid plan”).

Use simple language, clean layout, and yes—social proof if possible. If there’s a deadline (like when their trial ends), make that obvious. You want them to decide fast, without confusion.

Upgrade smarter, not harder

Your goal isn’t to flood inboxes—it’s to send the right message, at the right time, to the right person. Track usage data and segment users based on behavior. Someone who logs in daily? Send a nudge before their trial ends. Someone inactive? Try a reactivation angle.

Smart upgrade emails aren’t louder—they’re sharper. You’ll convert more customers with fewer sends, and fewer complaints about spam.

Let’s upgrade your email game

Want help crafting upgrade emails that actually convert? I’d love to chat. Book a quick strategy call and let’s turn your emails into revenue drivers.