Milestone emails: best practices with 12 examples

If you’re growing a SaaS product, milestone emails are one of the easiest ways to boost engagement and keep users moving through the journey.

But what makes a milestone email actually effective—and which moments are worth celebrating?

In this guide, I’ll show you how to send milestone emails that feel personal, timely, and build serious momentum.

Here’s what we’ll cover:

• Why milestone emails matter in SaaS
• The types of milestones that drive engagement
• Real-life examples from 12 SaaS products
• Tips to write and automate your own

Ready to turn small wins into big loyalty? Let’s jump in.

Why milestone emails matter in SaaS

In the world of B2B SaaS, milestones aren’t just celebrations—they’re powerful touchpoints for guiding users through the customer lifecycle. A well-timed milestone email gives users a reason to pause, smile, and keep going.

Whether it’s completing a specific milestone like setting up an integration or hitting a monthly usage streak, these emails reinforce value in ways that feel natural, not salesy. They also help boost key metrics like conversion rates, customer engagement, and brand loyalty.

💡 By showing progress and expressing gratitude, you're building trust—and that trust translates into revenue over time. These automated messages can be set up once and scaled easily, meaning you get long-term results with minimal lift.

Plus, these emails show that your company is paying attention. They can be personalized with data, triggered based on behavior, and optimized to keep users excited about what’s next.

In short? They’re tiny but mighty moments in your overall email marketing strategy—and they can seriously level up your customer experience if done right.

The types of milestone email marketing that boost B2B SaaS momentum

In B2B SaaS, usage-based milestone emails are the all-stars. These emails fire when a user completes an action—like booking their first meeting, publishing their 100th post, or using a feature for 30 days straight.

They’re exciting because they acknowledge progress, provide relevant information, and create a loop of momentum. When a user feels seen and celebrated, they’re more likely to keep engaging.

Then there are progress emails, which are fantastic for onboarding and habit-building. These might be weekly summaries, checklists, or streak reports that show how much the user has accomplished. They use data to validate effort and offer subtle nudges toward the next step in the customer lifecycle.

Add in a helpful email template, and you’ve got a powerful engagement engine. While subscriber's birthday messages are a staple in B2C, they’re less important in SaaS. Instead, focus on product anniversary emails, user anniversary milestones, and even your own company’s growth.

These moments can be turned into thoughtful campaigns that express appreciation and highlight your evolving services.

Whatever the event, milestone emails help send messages that feel timely, helpful, and human—all while strengthening your brand and community.

1. Calendly: Celebrating first meeting booked

Calendly celebrates a user’s first meeting with a vibrant milestone email that keeps the momentum going. It combines personalized messaging (“Congrats Jonathan”) with a clear next step: try another feature.

The layout introduces three additional features, boosting customer engagement and product discovery. This is a strong example of how to use automated messages to reinforce early wins and help users progress through the customer lifecycle with confidence.

2. Loom: Celebrating first video recorded

Loom sends a cheerful milestone email when a user records their first video—a key specific milestone in their product experience. The message pairs a celebratory tone with a clear call to action: share your video!

It also offers suggestions for what to record next, making the email feel helpful and action-oriented. This is a great use of automated messages to increase customer engagement and guide users toward building a lasting habit.

3. Apollo: Driving onboarding with progress emails

Apollo’s progress email tracks how far users have gone in setup and encourages them to keep moving. It turns onboarding into a mini-game, offering bonus credits as rewards for completed steps. This is a strong example of how to use automated messages and data to motivate behavior while boosting customer engagement.

The checklist-style format delivers relevant information that’s easy to act on, guiding users through the customer lifecycle with clarity.

4. Zapier: Celebrating first Zap created

Zapier’s milestone email fires the moment a user creates their first Zap—an exciting milestone in their automation journey. The tone is energetic and the content is useful, offering immediate ideas for what to build next.

💡 It’s a solid example of using automated messages to keep the customer experience flowing. By including relevant information and advanced tips, Zapier encourages users to grow their workflows and stay engaged with the product.

5. Duolingo: Encouraging learning with weekly progress emails

This cheerful anniversary email celebrates a full year of learning—aka a “Duoversary.” It’s packed with personalized data like words studied and phrases reviewed, reinforcing the user’s progress and showing tangible impact.

The playful design and celebratory tone make the customer experience feel joyful and motivating. This is a great example of how user anniversary emails can strengthen brand loyalty, boost retention, and invite users to continue their journey with purpose.

6. ZigZag: Product anniversary emails

ZigZag’s anniversary email marks a major company milestone—10 years in business. It blends storytelling, social proof, and product evolution to reconnect with its audience. Instead of just celebrating, the email highlights new features and invites readers to book a demo.

It’s a great example of turning company’s growth into a meaningful campaign that boosts brand loyalty, reinforces expertise, and gently ties celebration to revenue-driving action.

7. Grammarly: Reinforcing value with weekly progress emails

Grammarly sends beautifully detailed progress emails that celebrate user streaks, tone usage, and vocabulary growth. It’s a masterclass in using data to create a sense of achievement and reinforce product value.

With clear visuals and personalized messaging, this email keeps users engaged while gently nudging them forward. It’s an ideal email template for driving customer loyalty, especially when you want to show—not just tell—the impact of your services.

8. Semrush: Celebrating user anniversary with gratitude

Semrush’s “Semrushversary” email celebrates the user’s one-year milestone with warmth and appreciation. It’s a classic user anniversary message that helps strengthen brand loyalty and build community. The tone is friendly and thankful, reinforcing the value of long-term relationships.

This anniversary email is a great reminder that sometimes the most powerful messages are the simplest: a little expressing gratitude goes a long way in increasing customer engagement and future conversion rates.

9. Miro: Highlighting a year of activity with product recap

Miro’s milestone email wraps up a user’s year with playful graphics, highlights, and personal usage data. It’s like a mini product anniversary celebration packed with delight. From “your go-to emoji” to “most productive day,” it shows users how much they’ve done—and inspires them to do more.

This is a great example of combining automated messages with relevant information to increase retention, reactivation, and a little joy in the inbox.

10. Loom: Recapping monthly performance with data-driven insights

Loom’s monthly progress email highlights how many meetings you avoided, videos you made, and time you saved. It turns usage into clear ROI, keeping the value of the product front and center. These automated messages are smart, simple, and personal, helping customers see the impact of their efforts.

If you’re looking to improve email marketing touchpoints during active usage, this is a perfect email template to create from.

11. Buffer: Celebrating posting milestones with social proof

Buffer celebrates an exciting milestone: a user publishing 355 posts in a year. The email adds social proof by noting they’re in the top 15%—a great way to drive pride and continued action. It’s a mix of personalized messaging and subtle encouragement that reminds users how far they’ve come.

This type of milestone email reinforces routine usage while strengthening the relationship between company and customer base.

12. GoDaddy: Monthly milestone reminder email for account review

GoDaddy sends a no-frills milestone reminder email to prompt users to check their monthly account summary. It may not scream “celebration,” but it plays an important role in maintaining trust and transparency.

It’s an essential part of the customer lifecycle, especially for platforms tied to subscriptions, services, and renewals. Even small reminder emails like this help acknowledge the relationship and offer relevant information that keeps users engaged and informed.

How milestone emails improve customer retention over time

Retention doesn’t come from one big move—it’s built through small, consistent wins. A well-timed milestone email keeps users feeling seen, appreciated, and supported across the customer lifecycle.

Whether you’re sending a progress email, a product anniversary recap, or a thoughtful milestone reminder email, these touchpoints help reduce churn by reinforcing value over time. They’re especially powerful when paired with personalized messaging that reflects actual data and usage.

Celebrating special occasions, big or small, reminds users they’re part of something ongoing. Ultimately, these messages aren’t just about moments—they’re about momentum.

When you create consistent, feel-good milestones, you’re building long-term loyalty, increasing conversion rates, and making your brand one users want to stick with.

Using milestone emails to drive upsells and feature adoption

💡 Milestones don’t just retain users—they can drive growth too. Smart SaaS teams use milestone emails to introduce advanced features, highlight upgrades, and encourage the next step in a user’s journey. For example, hitting a usage threshold?

Celebrate it—then invite them to explore premium tools. Shared 10 videos? Unlock analytics. This is a subtle way to surface services, promote discount codes, or seed a limited time offer. When tied to a real event, upsells feel timely, not pushy. It’s all about context: matching a user’s success to what they need next.

With relevant information, helpful CTAs, and the right email template, these campaigns can boost revenue without ever feeling like a hard sell.

Great customer experience starts with celebrating your users

When it comes down to it, milestone emails are about more than engagement—they’re about relationships. They show your customers you’re paying attention, you care about their progress, and you’re ready to help them grow.

From first actions to feature mastery, from anniversary emails to recap reports, these moments make your email marketing feel less like noise and more like a helpful nudge. They increase loyalty, reinforce value, and drive long-term customer experience improvements. The takeaway? Don’t wait for users to wander—acknowledging their journey keeps them on track.

Whether you’re a startup or scaling fast, celebrating your users’ wins is one of the most powerful ways to grow your business and your brand.

Let’s send milestone emails that actually matter

If you’ve read this far, you probably care about sending better emails—and I’m here for that.

I work with early-stage SaaS teams to build milestone emails that feel personal, drive real customer engagement, and move the needle on retention and revenue. Whether you’re just getting started with automated messages, or want to improve the ones you already have, I’d love to help.

We’ll identify the best types of milestone moments in your product and turn them into messages your customers actually want to open.

No fluff, no spam—just helpful, well-timed nudges that build loyalty.

Sound good? Send me a message or book a strategy session—I’d be happy to chat.