How to Write Engaging Transactional Emails, featuring Beth Dunn


BY  JOHN BONINI Think back to the most important email you sent last month. What comes to mind?


Think back to the most important email you sent last month. What comes to mind?
For most, it may have been a newsletter that generated a lot of new product signups. Or maybe it was an upsell campaign that increased the customer lifetime value of an important segment of your customers. It could even have been a top of funnel promotion, promoting a new piece of content to great success.
Any of these would certainly qualify.
But it’s also possible that the most important email you sent last month was actually written months ago—in the form of a transactional email.
Transactional emails are any emails sent based off a subscriber’s behavior. Also referred to as “triggered” emails, these can range from:
…among many others. Depending on the size of your database, these types of emails could be sent anywhere from a few hundred to a few hundred thousand times a day. But because they’re setup to send automatically, they’re easy to overlook.
They also have a tendency to sound a tad robotic. The more routine the transaction—think “your download is ready” type emails—the more ordinary the subsequent email tends to be.
But these are exactly the types of opportunities Beth Dunn relishes.
Dunn, product editor in chief at HubSpot, is no stranger to the art of transactional emails. HubSpot, an inbound marketing and sales software company, has over 18,000 customers. As you can imagine, they have a lot of opportunities to think about transactional email.
Dunn has been with HubSpot for over six years, has seen it grow from the early days of the inbound marketing movement to a successful IPO in 2014, and frequently speaks on the role content and copywriting has played in it all.
Here is our conversation with Beth Dunn on the art of writing compelling transactional emails that are delightful, on-brand, and most importantly—effective. (Full recording below.)
Q: First, for our readers who may not be as familiar with your work, could you share a little about yourself?
My official title is Product Editor in Chief, which means I’m the writer and editor of anything that appears on the product side. [This includes] in app messages, alerts, or any words or phrases you see on screen while using the product.
It also includes any emails that are triggered by the HubSpot Software. Lead revisit notification emails, if you uploaded a CSV of contacts and get an email that your files have finished uploading—all of those seemingly pedestrian notifications are all opportunities for delight, happiness, and to continue the HubSpot voice and tone.
Alongside that, I’m also the internal evangelist on how to sound “HubSpotty”.


Q: Most brands overlook those so called pedestrian emails. How do you use those as opportunities for delighting people?
I think the most important thing when you’re thinking about that kind of email is to look at it in context.
The most important thing for me is to consider what just happened prior to this email going out. Is the person sitting there waiting, are they impatient, have they already moved on to another task—you really have to think about what the user is going through the split second before your email shows up in their inbox. You really want to strike the right tone based on what their emotional state is going to be.
“You really have to think about what the user is going through the split second before your email shows up in their inbox.”
I do a fair bit of user testing to make sure my assumptions are right around this sort of thing. Given all this research, if everything else is appropriate, then I just try to make people smile and provide a light hearted moment.
The earliest examples of these emails I did was a signoff that went something like, “by the way that shirt looks great on you today”, you know, something we’d all love to hear.


Q: Given the transactional nature of these emails, do you ever get to hear feedback?
You’d be surprised, we get a lot of feedback. What people usually do is, since they’re still in the app, many screens have a ‘help’ button or feedback popup, and people will go out of their way to connect with us through there to say, “that made me laugh.”
People go out of their way to provide feedback, which is very helpful. I find that HubSpot users are a particularly vocal crowd, which makes my job very easy.


Q: What types of user testing are you employing?
It’s very conversational. The way that we approach user testing is we’ll usually isolate a particular task, and recruit some people from our database who have performed that task on a regular basis—or don’t at all depending on the goals of the research—and come up with a script that directs them toward triggering this action so we can see what it is they naturally do.
You’ll see people go over to Facebook, or get up and get a cup of coffee—most of the time they’re visiting Facebook—so they interrupt what they’re doing. It’s helpful to see how people’s normal workflows are.


Q: How do you work your findings into the emails?
You want to be careful about this sort of thing, because it can come across as creepy. You have to think about whether it’s going to come across as light-hearted, which is what I strive for, or not.
You’d be surprised at how things can be taken badly.
What I try to do is think about a particular person that I have known in my life that takes offense at the slightest thing. We all know these people. If they can twist our words and change it to their meaning, they will. I imagine this person getting this email on their worst possible day, and I try to write my email so that this person could not possibly misconstrue what I’m trying to say in this copy.
The main thing to keep in mind is that your job is to make the user’s job easier. My job isn’t to make you like me more, or like HubSpot more; as long as I’m really staying focused on the user and how this help her get her job done, get her job done faster and more happily, then I tend to stay on course.
“The main thing to keep in mind is that your job is to make the user’s job easier.”
Q: What are some subtle delight factors that people can think about when writing transactional emails?
The first thing is to give them the information. I see some examples of product triggered emails where people get too caught up in making the user laugh and the actual helpful information is buried in the third paragraph somewhere.
This is tweet-sized content we’re talking about. You don’t really have a a lot of time.
You want to make sure that the information you’re trying to convey is in the subject line and also the first thing they see in the email. What I usually do is put the humor in the signature line or in a PS, so if they have the time and inclination to keep reading, then they’ll get a little smile.
And try to keep these fairly general interest. HubSpot is an international product, so we have to make sure things are going to translate into different cultures and languages properly. You don’t want to make narrow pop culture references–you have to think about all these things.
You really have to know your persona. At HubSpot, our main persona tends to be a fairly mature, mid-career professional. If we write referencing a Taylor Swift song, it’s not going to achieve any delight or what we’re trying to do.


Q: How long should a transactional email be?
It’s kind of like the age old question about what’s the proper length of a blog post, and I think the answer is that it depends.
You have to do a lot of testing to see what works for your particular user base, because it can vary based on customer persona, industry, the day of the week and the type of content you’re trying to convey.
So I would say, first and foremost, be willing to experiment, look at the data, and test all of your assumptions.
“Be willing to experiment, look at the data, and test all of your assumptions.”
Q: How do you approach the ask—the upsell, download, product engagement—in a transactional email tastefully?
I tend to think in terms of what would be most helpful to the user at this time. Again, it’s a matter of removing the lenses that we tend to have on which say, “what do I need out of this?”
Whether it’s a conversion or an upsell, that’s not really what’s important. What’s important is what the reader needs next. If what you’re offering is sincerely what they’re looking for, and they’re going to say “Thank you for that link. THANK YOU!” then it’s the right thing to do.
If not, then I think you have to rethink how you’re presenting the ask. Maybe you don’t go for it in the email. Maybe you present more helpful, educational content that has the ask within it rather than including it in the email itself.


Q: What’s one thing you wish more emails were able to achieve with their copy?
Stop using exclamation marks. It’s like my thing at this point. I feel like copywriters everywhere are doing themselves a disservice by leaning on exclamation marks to get the reader excited.
Exclamation marks don’t get your readers excited, exciting content gets them excited. So I cringe when I see an email that has an exclamation mark in the subject line, the greeting, the salutation, and it’s just like, stop.
I’m not 100% against it, or saying you should never use them. But you really have to be super sparring with them, otherwise they lose whatever effectiveness they do have.
If you find yourself over-relying on exclamation marks, I think it means you need to go back to your words and give them more punch.



  • Consider what the user is doing and/or going through the split second before your email appears in their inbox.
  • Focus on positioning your content and/or promotion in such a way that helps make the user’s job easier in that moment.
  • Get to the information first. Make sure your main point is in the subject line and also that it’s the first thing a reader sees in the email itself.
  • Be willing to experiment, measure, and test all of your assumptions.
  • Don’t go for the ask unless you think this specific user would thank you for doing so.
  • Don’t over-rely on exclamation points to get your readers excited.




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#DIGITAL: How to Write Engaging Transactional Emails, featuring Beth Dunn
How to Write Engaging Transactional Emails, featuring Beth Dunn
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