Most SaaS teams are not failing at personalization because they lack data. They are failing at execution.

One of the most common mistakes is using the data to personalize appearance instead of context. The email looks tailored, but it does not reflect where the user is, what they are trying to decide, or what would help them move forward.

Such “personalized” emails still feel generic or irrelevant.

The goal of personalization is not to prove that you know the user. It’s to reduce friction in their decision-making.

Here are common personalization mistakes that stem from this gap and how to improve your email marketing strategy.

Ignoring Product Usage Context

Example scenario: Sending an upgrade email to a user who is still onboarding.

Sending generic one-size-fits-all messages to active users fails to capture the context of the usage, even when the wording perfectly captures their personal details.

A user’s stage—trial, onboarding, active, inactive, churned—makes a big difference in your messaging. It influences the level of details and type of offers.

When you fail to consider where the recipient is in their product usage, you create friction that can slow down decision-making.

For instance, prompting a user to try out new advanced features when they are still figuring out your basics can overwhelm them. It can make them question whether the product is the right fit.

Relying on One Criteria for Segmentation

Example scenario: Sending team plan discounts to a solopreneur.

Focusing on behavioral data and ignoring firmographic data like company size can result in irrelevant emails that are ‘noise’ to the recipient. It can make them feel spammed and signal that you don’t understand their needs.

Combine relevant data of how the recipient interacts with your product and why, with key data points that tell what their business is.

The result is highly relevant emails that feel like a ‘personal conversation.’ This improves decision-making for the recipient and drives engagement and conversions.

Lack of Trigger-Based Emails

Example scenario: A user activates an add-on and does not complete the onboarding process, but there’s no follow up email sent to guide them on the next steps.

Trigger-based emails are one of the most personalized and contextually relevant types of emails you can send.  They provide high-value and timely information that can get the user unstuck, speed up product adoption, and reduce churn from frustration.

Pay attention to these opportunities for trigger-based emails that are easy to miss:

• An upcoming trial expiration
• A credit card that’s nearing expiry
• After a critical milestone, such as creating the first project
• When a user has been active but failed to use a high-value feature that would be relevant to their usage context
• When a user is nearing their capacity limit

Ignoring the Why of Your Email

Example scenario: A long-time active user receives a personalized email highlighting a feature they already use, with the copy: “Since you use reporting, here are some ways teams use reporting.”

Nothing is technically wrong with the above scenario. The data is accurate. The timing makes sense. The email does not introduce a new or meaningful decision for the user because they already use the feature. They are not deciding whether to adopt it.

The primary purpose of personalizing emails should be to help the recipient with decision-making, not just make them feel seen.

So instead of asking ‘How do I personalize this email?” ask “what problem does this email help the recipient solve?”

In our illustration, for instance, the recipient is deciding:

• Is this worth deeper investment?
• Should I expand usage to my team?
• Should I renew or upgrade?

An email answering these questions would be more valuable to them.

Assuming that Personalization Means More Information

Example scenario: A VP of Operations receives an email that references multiple tracked actions in one message: the exact webinar they attended, the comparison page they viewed, and the fact that their company just raised a Series B funding. The email then pitches a demo.

More is not always better when it comes to personalization. Email recipients want to feel that you know them, but they don’t want to feel watched. It can create hesitation, especially when you are dealing with decision makers in companies.

To create a connection, and not a breach of trust, use contextual, relevance-driven information.

Anchor personalization to the decision the recipient is trying to make, not to everything you can track about them.

Key Takeaway: Prioritize Context Over Data Points

When emails focus on what can be tracked instead of what needs to be decided, the message may feel tailored, but it does not help the recipient move forward. In some cases, it slows them down by creating confusion or mistrust.

Strong personalization respects context and is anchored to decision-making. Before hitting send, ask yourself: Does this message make the next decision clearer for the recipient?