Design Transactional Emails to Boost 10X Sales – Email Delivery
Written by
Benjamin Brandall

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Design Transactional Emails to Boost 10X Sales – Email Delivery

Published : May 7, 2019

The automated emails you send customers are usually either Marketing sequences or sent on a Transactional basis, triggered by interaction with your site or product.

Most SaaS companies run lead nurturing campaigns in parallel with behavioral emails to share information about things the user has done — but transactional emails shouldn’t be treated as a purely functional channel and separated from marketing. Here’s why:

Transactional emails are 69% more likely to be opened than marketing emails, and 165% more likely to be clicked, according to research by Epsilon.

Since context, relevance, and timing are all factors that affect a message’s ability to drive action, why not leverage that power for Onboarding, upselling, and free trial conversion?

In this article, we’ll see why you should pay more attention to transactional emails, and share best practices to follow from case studies and real-life examples. We will see how to create engaging transactional emails.

What are Transactional emails?

Transactional Emails are Triggered by particular user actions. They’re Automated and Context-Driven.

“A user’s action triggers a transactional email. These emails are usually automatically generated. They occur when you fill out a form, do a payment, check-out online, ask for a password reset, etc. These emails are generated and are rule-based. Transactional emails are sent through SMTP relay or APIs.” Pepipost

For example, when you register for a new tool, you get a welcome email. Or, when you buy something online, you receive an email with the order confirmation.

The biggest difference between transactional and marketing emails is that transactional emails are sent to one person, while marketing emails are sent in bulk to many subscribers, like newsletters or promotions sent to all subscribers.

Because transactional emails are triggered by an event or user behavior, they are extremely relevant to the user’s context and motivation. This can be leveraged to:

  • Onboard users
  • Improve retention
  • Reduce churn rates
  • Improve trial-to-paid conversion
  • Upsell products or premium plans

Now we know the importance of transaction email, let’s look at some great B2B use cases where they shine.

Using Transactional in user Onboarding Emails

In the early stages of the user journey, meeting expectations, providing guidance, and selling your product’s benefits is vital. Transactional emails help meet all of these goals:

Welcome emails

Promotional Mailings


Receiving a Welcome email when signing up is a time-tested pattern — and emails that users expect to receive get better engagement. According to Invescpro, 74% of people expect to receive an email welcome when they sign up somewhere.

There’s a disconnect here between users and businesses because only 57.7% of companies are sending welcome emails. If you still didn’t implement welcome emails, this is a great opportunity for you to leverage the user’s attention and motivation early.

For SaaS products, welcome emails are a great opportunity to lead your trial users towards their “aha moment” and drive feature discovery.

Let’s have a look at this example from Asana:

Asana Welcome Email

What can we learn from this example?

  1. Use emotion in your headline. Here, Asana makes users feel included
  2. Guide users towards the events most strongly correlated with activation. By simply explaining how to start using Asana in three steps, this email pushes users towards the first activation event (creating and completing a task with a due date)
  3. Use only one call-to-action. Asana includes one clear, eye-catching and intuitive button rather than linking off to help docs, blog posts, and other distractions.

Here’s another great welcome email by InVision:

Invision Welcome Email

Besides the predictably wonderful design (it’s InVision!), what else can we learn from this example?

  1. Personalization = better engagement – try to personalize your transactional email as much as possible. Here, InVision uses the first name of the recipient in the headline to reassure the reader that the message was really meant for them and create a sense of inclusion. According to Campaign Monitor, emails with personalized subject lines are 26% more likely to be opened.
  2. Offer help preemptively – Point your customers towards your knowledge or resources page.

As you can see, welcome emails can do far more than just inform the user that their signup was successful. They can put users on the path to deeper engagement and provide simple product education.

Teach users to Use your tool

User onboarding is about guiding users to the new value. As a form of product marketing, it’s a mix of feature education and messaging that sells the benefits.

Transactional emails for onboarding don’t necessarily need to be triggered by a user action; they also could be triggered when a user doesn’t engage with a key feature or prompt. In a case like that, you could trigger emails to educate a user what can they achieve with it, and why they should use it.

Here’s one example of how Status page teaches users to get the most out of a feature that improves the tool’s usability and makes it easier to publish error-free updates: Tips


What can we learn from this example?

  1. From just a quick glance, the header clearly shows users what can they achieve with this feature.
  2. The actionable video demonstrates how to use incident templates – this will deflect support tickets related to the feature and persuade more users to adopt it
  3. The text under the video sympathizes with customer’s pain points using relatable language.

But, this is not the only onboarding email in Statuspage’s arsenal. They have a series of 5 transactional onboarding emails which demonstrate 5 key features. But, the thing is, they only send the emails with feature demonstrations to the users who didn’t try that particular feature.

According to the Statuspage team, these onboarding emails helped to achieve a 2.4x lift in trial to paid conversion.

Behavioral user onboarding emails

If you want to know when it’s the right time to trigger your trial users, it’s essential to track their in-app behaviour. For example, if you are a CRM company, and you realize that your trial user didn’t import a contact list (this can be a very good activation event), you can send them a transactional email reminding them to do that and explaining why it matters.

Based on your key user activation events, you should set up different transactional email cycles.

Competitors App – a tool for monitoring your competitors online – provides a great example of how to use behaviour-based transactional emails to attract customers and empower your trial users to take action.

For new signups, the first essential action is to add you and the domains of your competitors. If a user didn’t add domains after a certain length of time, it sends its users this email:

Competitors App Add Your Domain Transactional Email

What can we learn from this example?

  1. This particular email is triggered by the user’s behaviour, and it motivates the users to take action – so they can see the value of the tool (insights into what their competitors are doing)
  2. It’s short, catchy and straight-forward.
  3. Although it’s obvious – sending your transactional emails from a real person (or in this case from a CEO’s email), it makes users more engaging and it shows them that this is not “another generic email”.
  4. It’s also a great example of offering your help even if your user didn’t ask for it.

Wondering how this particular email helped them to improve user onboarding?

Razvan Girmacea, CEO of Competitors App, shared with us the results:

“This particular email has an open rate of almost 50%, and over 30% of these people who opened an email added their domain – which we consider the first activation event in our user journey.”

According to GetResponse’s email marketing benchmark, the average open rates are just over 15%.

Here is another great example. Let’s see how Venngage reminds its users to complete the action and leads them towards a key user activation event:

Vennegage Reminded

What can we learn from this example?

  1. Venngage’s team offers compelling reasons for their users to come back and finish the infographic they started – to abolish boring, text-heavy content
  2. With the catchy image and funny text, this email establishes Venngage’s playful brand (and tugs on the user’s heartstrings!)

In these three types of transactional onboarding emails, we’ve covered almost everything you will face when welcoming your users to your tool, teaching them how to use your most important features, and activating them through triggered and behavioural emails.

Now, when your user’s trial journey is close to conversion, let’s see how to leverage the power of transactional emails to drive retention.

Trial expiration emails

Usually, the practice is to send trial expiration emails 24-48 hours before the trial ends.

Have a look at this example from Squarespace:

Squarespace Trial Expiration

What can we learn from it?

  1. Create a sense of FOMO. Here, Squarespace uses a very mildly-worded threat (“ensure your website stays live”) to hint at what the user could lose and prompt an upgrade
  2. Surface your most important premium features. Instead of hiding its premium features in the body text, Squarespace highlights them with self-explanatory icons
  3. Offer customer support whenever you can and make sure that your customers understand that you care about them. Questions about upgrading can quickly become sales calls!

Now we’ve seen some prime user onboarding examples, let’s explore transactional emails for marketing to your existing customers.

Marketing to your existing customers with transactional emails

As we mentioned at the beginning of the article, transactional emails have a place at almost every step of the user journey and sales funnel.

For example, you can remind your customers about special events, webinars, try to upsell bigger packages or notify them about failed payments and credit card expirations.

Let’s check some of the best examples and what we can learn from them.

Nurture your customers through content

Transactional emails are a great opportunity to nurture your customers through content and prepare them to upgrade plans or engage more deeply.

For example, you can use transactional emails to teach your customers about the benefits of premium features.

Intercom uses transactional emails to notify their users about upcoming webinars with the purpose of driving feature adoption across users who aren’t making the most of the platform

Intercom Webinars


What can we learn from this example?

  1. With webinars, Intercom nurtures its leads and upsells premium packages. The offer leads to the right mix of education and marketing.
  2. Intercom clearly shows the reader what are the benefits of their premium features and what they can exactly learn from watching the webinar

Upsell features and bigger premium packages

Transactional emails are closely related to your product and its features, so they can be effective at showing the user what extra value they could get, while using tangible examples that are custom to the recipient.

For an example of this in action, let’s see how Crayon uses transactional emails to upsell the Pro version of the product:

Crayong Transactional Email Upsell

Crayon sends reports to its user through transactional emails. This is a perfect opportunity for them to present to their users that deeper, more valuable information is available at extra cost. 

What can we learn from this example:

  1. Crayon offers its users an incentive to sign up for a premium plan, playing on the motivation to know in-depth business intelligence and the fear of being behind on competitor activities
  2. They are offering some value before asking users to pay

The bottom line

As you can see, transactional emails can be powerful not just for conveying information to users, but as a way to support strategies that lead to trial conversion, feature adoption, and premium upgrades. You can use them both to onboard new users and market to your existing customers, especially if you run a free trial or freemium business and track user behaviour.

Although there are hundreds of great examples out there of how to properly use transactional emails, we’ve shown you some of the strongest for inspiration in your own campaigns.

What will be the first transactional email you’ll upgrade?

Let us know in the comments!

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