Best practices for sending personalized transactional email

Editor’s note: We recently released and wrote an all new guide that dives deep into modern best practices for sending transactional emails as well as a complementary guide on Gmail Inbox Actions.

Has someone ever come up to you in a coffee shop and started a conversation? When it happened, how did you feel? If you’re like most people, when someone was friendly in a genuine way, you felt good.

Human beings are social creatures, which means good interactions with other people feel great. When we have a good social interaction, the brain releases a little bit of dopamine and oxytocin (chemicals that make you feel good). This release causes us to want more of what caused the good feeling.

It’s hard to be friendly in a genuine way. To go up to someone you don’t know and have a conversation with them requires courage and a willingness to get rejected. It feels great to be the recipient of friendliness, but actually being friendly is quite hard.

Your company’s transactional email is a great chance to be friendly with users. When your users receive friendly transactional emails, they’ll feel a personal connection to your product. Because your product makes them feel good, they’ll like it more.

You send friendly transactional emails by personalizing them. Here are 5 ideas for personalizing them.

1. Use a from address, from name, and reply-to email address with a person’s name #

What happens when you meet someone new after exchanging greetings? You immediately exchange names because hearing someone’s name builds trust. If the recipients of your transactional email see that there’s a real person sending it, they’ll feel more connected to it. It will also build trust.

So, for Postmark, if I’m the one to send a transactional email the From name could look like Jack at Postmark. Ensure the name on the email address sending the transactional email is the name of someone working at your company. Also, make sure that the person whose name is on the email address is the person who will reply to emails. It’s disingenuous if you don’t do these two things.

This personalized strategy usually works best for drip emails. For automated emails like shipment confirmation or receipts, it makes more sense to come from your product.

This email is from a real person at Quip which makes it feel friendlier.

2. Greet the recipient by their first name #

It’s a psychological fact that people love to hear their own names. Today, people often greet each other with just “Hey” or “Hi,” and don’t use other people’s names in greetings. I’ll admit I sometimes do this when talking with friends or people I know, and it’s a shame. When we don’t address the people we know by name, we miss an opportunity to connect deeply with them.

If possible, always try to address recipients by their first name. Here is a good example from CoSchedule:

Coschedule greets me by first name, which is fantastic.

3. Tell users at the end of each email that they can reply any time with questions #

Most customer support is a disaster. Imagine Comcast, Dell, AT&T, your insurance company, Rite-Aid, or any company with terrible service. How do those companies make you feel? With the bar set so low, having friendly and fast service is a great way to stand above the crowd.

A simple, but very effective way of making your support better, is making sure that you give your users a fast and easy way to get help. Insert a line at the end of each transactional email telling customers they can ask a question at any time by simply replying to this email. This is a great way to make your emails more friendly and improve customer support.

People will appreciate that you encourage them to be open about any problems they experience. And, they’ll likely take you up on your offer from time to time. This part of the email should be short and sweet, and it can come right before you sign your name. Or it can go in a P.S. section in your email.

This email includes text at the end that encourages me to reach out to support.

4. Use plain text in your personalized emails #

This is a strategy reiterated by Nathan Barry. Think about the most recent email you received from a friend. What did that email look like? It likely contained only plain text. There probably weren’t any fancy images or layouts in the email. It said what it needed to say, and didn’t have any visual clutter. Now, imagine a friend sent you an email that looked like the following:

A screenshot of a rich-text email that includes a bunch of ancillary content.

By using plain text, you can start a conversation with your customers. The welcome email above is quite nice, but it’s not something a customer would reply to for more help. We tend to like personalized emails that come from a recognizable person at the company, which helps build trust and a relationship with customers or users.

Of course, not all emails should be plain text. A good example is a receipt or shipment tracking email. And don’t forget, true plain text emails cannot track opens. One trick is to design an HTML email that looks like plain text, this way you can still track the effectiveness of your messages.

5. Include an image of the person who “sent” the email #

At the end of your transactional emails, the person who “sent” the email should sign off using their name. Next to the name of the person who’s signing off should be a small picture of them. Including a picture of the person who sent the email will instantly make it friendlier. When we see a picture of someone next to their name, we put a face to their words.

One easy way to do this without sending HTML email is to add a photo to your Gmail account. You can do this by setting up a Google+ account and When you do this, Google+ will populate emails you send with your profile image. Just make sure your profile image for Google+ is appropriate or in line with the business or product. Additionally, many email clients like Airmail, Thunderbird, and Postbox now support Gravatar and will pull in your avatar automatically.

Including a photo of the person who "sent" the email keeps it human.

Keep it friendly and helpful #

These are 5 strategies for making your transactional emails more friendly and helpful. Creating friendlier transactional emails will help you earn trust with your customers and users. Give them a try and let us know how they work for your app.

Jack Kaufman