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Personalized Milestone Emails - A Winning Retention Strategy for Product-Led Growth

Usha Vadapalli
January 10, 2023

Product-led growth companies (and their investors) rely on Net Revenue Retention (NRR) as the key metric to understand and gauge the overall health and sustainable growth of their businesses. We calculate NRR using this formula

Source: Subscription Flow

It is pretty evident that account expansion, churn and contractions play a pivotal role in determining the success of the PLG business. Focusing on a user retention strategy that helps in all three areas is a good idea to improve NRR.

If you are wondering what retention strategy addresses the problems with scaling up accounts, churn, and downgrades, you need to know more about PLG milestone emails.

What are Milestone Emails?

Milestone emails are triggered when the users cross or need a nudge to reach an important inflection point in product usage.

Sending milestone emails is important because they

Deliver positive reinforcement to new users to encourage returning to the product

  • Create sticky users with a nudge when they are stuck clueless or inactive
  • Remind users of the product’s value and impact
  • Build product champions and earn loyalty

Milestone emails help reduce activity churn with timely intervention.

Let’s take a look at some examples of PLG milestone messages that can be sent at different stages of the customer journey.

Complementing Onboarding

When a new user signs up to try out a product, they need to stick around long enough to experience its value. We need to keep the time to value (TTV) short to retain the user’s interest. A personalized onboarding experience is the first step toward user retention in a product-led growth business.

Completing the onboarding process is an important milestone for a newbie user. Make sure you celebrate the user’s baby steps with them while guiding them to the next course of action.

Polly does exactly that. They send a milestone email celebrating the first poll sent and encourage users to complete onboarding and lists out tips on how to send the next one.

Celebrate Quick Wins

Clicking the send button on a campaign can be nerve-racking. We, at Inflection, love celebrating that bravery! This is the email we send to celebrate our customers’ first campaign launch.


The goal of this email is primarily to encourage product usage and give them confidence about being on the right path. These emails can continue to be triggered at different milestones along the user’s product journey.

The first aha! Moments are different for each product but the joy of making it to the first milestone is commonly experienced. This moment can influence the decision to convert to a paid user early on, in a big way.

The celebrations need not stop with the first win. Continue showing appreciation by sending them a high-five at every milestone along the way.

Canva uses badges to show their continued appreciation to the users at each milestone.

These look great for bragging on social media, BTW. The user gets bragging rights, and Canva gets their loyalty and word-of-mouth marketing. Win, win!

Value, Appreciate, and Show Them What’s Next

The celebration email is a great way to get your customer’s attention. Use it to deploy them on their next mission.

We talked about Canva’s badges already. They send these amazing badges in email with a gentle push to take the next steps.

Be extra helpful about the next action item, especially if your product has a steeper learning curve. Segment is another example. They relay the successful connection message and clearly lay out the next step with their product.

Product adoption doesn’t stop with the first few milestones. Keep delivering a delightful and positive experience while nudging them towards adoration.

Gamify The journey

Along their way to conversion to a paid customer, users need a delightful experience to stick to the product. Grammarly is one of the best case studies of gamified product usage. Right from the sign-up, they send encouraging messages, show the progress of writing using Grammarly, and unlock features as the user progresses. A series of milestone emails personalized to the user’s writing activity and goals.

The goal here is to create sticky users and keep them on the path to conversion with a lot of cheering.

Do what Grammarly does to keep your customers coming back for more.

Encourage Expansion

Scaling up existing accounts can be easier than acquiring new customers. Milestone emails can support campaigning to up-sell or cross-sell to your customers.

Check out this flattering and personalized email from Mural.

They acknowledge the user’s achievements before encouraging them to invite more team members. And, they state a reason why. Products that deliver more value with a network effect (more users or orgs connected, more value. For example, Slack) can steal this idea right off Mural’s playbook.

Tips To Craft Impactful Milestone Emails

Do all milestones get conversions or other expected results?

Not quite.

The products are different or the product-led growth models vary. The PLG milestone emails have to be relevant to your PLG strategy, your business goals, and the product’s learning curve.

Here are some of the best practices to get the milestone emails right

  1. Personalization

The first and foremost factor that decides the success of any campaign is personalization.

In a product-led environment personalization not only means the customer’s firmographic data but also their product behavior.

Sending an email to invite more team members to an individual using your product for a personal project. PLG companies need to understand the user and their goals to get the personalization formula right.

Segment your users based on their product activity. For example, their familiarity with your product — newbie, intermediate, power user, etc., along with CRM data like clicking on the help button, attempting to access a gated feature, etc. For any milestone email to be impactful, you need to use a wholesome mix of product and CRM data.

Personalizing at scale can be easy or not so easy depending on how you do it. We built Inflection to solve this problem for product-led growth companies. We help PLG teams drive revenue, product engagement, and speed up onboarding at scale without the dependency on data or engineering. Get started here to watch Inflection in action.

  1. In sync with product milestones

Milestone emails show how much you appreciate your user’s association with your product and business. However, if you are limiting them to anniversaries, they are not motivating enough for the user to return to your product.

Figure out the important product milestones your power users and best customers journeyed through to get to where they are. These are your ideal trigger criteria for milestone emails. Analyze and optimize these triggers to deliver a personalized message with the right context.

Aligning the milestone messages with notable product events gives you the best leverage to activate disengaged users, hand-hold users at the sticky parts of the product, and ultimately prevent churn.

  1. Actionability

Valuing and appreciating your customers is a great way to earn their loyalty. Your milestone messages are not very useful if they don’t nudge the customers to take action.

You need to give them reasons and motivation to keep going back to the product to actually experience its impact in solving their problems. Show them what’s next and exciting in the product, how far they’ve come and how little it takes to get to level up, and reward them for taking positive action.

Personalized Milestone Emails - A Winning Retention Strategy

Acquiring new customers is exciting. New customers mean new revenue, and who doesn't love that?  But, it’s not the only way to grow and succeed though.

Retention has a huge impact on your revenue, especially in a downturn. It has always been a hot topic in the product-led growth community for obvious reasons. Retaining customers has a lot to do with mitigating churn. And, the best way to mitigate churn is to see it a mile away and avoid it.

Personalized and product-led milestone emails delivered at the right time are one of the best ways to mitigate activity churn. Show them appreciation, give them reasons to stick with your product, help them at tricky turns, and celebrate their wins. You can earn their loyalty on top of slaying churn.

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