What are some major takeaways you can share about your email on-boarding campaign?

FABIO: I feel that simplicity and clarity is important. At the same time, it’s important to keep in mind that those two things shouldn’t come at the expense of good, comprehensive content. Though providing a new user with lots of information can make the on-boarding process overwhelming, the danger of that can be mitigated when you furnish them with prescient, relevant content in easily-digestible chunks.

It’s the quality that’s important; the quantity can be played around with.

BRADLEY: With our on-boarding marketing emails, after a few iterations — and three years of sending — we’ve learned quantity isn’t super important. Whether it’s a series of three, five, or 10, we just need good content, and we can add a new email without cutting another.

Also, we don’t have to corral messages into the first few days. Because most users don’t try everything at once, we’re able to space deliveries more closely to match when someone’s likely to add automation or discover a similar segment. And more than explaining each topic step-by-step, our on-boarding helps remind folks that our app is pretty powerful and we have resources available whenever they’re ready.

We’ve also started separating on-boarding content based on the profiles completed when an account’s set up. Using basics like the age of a company or if they’re importing an existing list, we can estimate a subscriber’s interests. It’s not perfect, but it helps us make an attempt toward relevant info right away.

How do you track how effective each email campaign is? Any suggestions for those starting out?

FABIO: For our transactional emails, we make use of Mandrill and its myriad reporting features. Tracking open and click rates is a simple affair; studying and playing with the things that affect those rates is the trickier bit. We do that a lot, however-to us, transactional emails represent a playground for email design. There’s a lot of room for experimentation in the development, design, and content arenas, and that’s my advice to anyone starting out: always experiment. Develop the emails using different techniques, be open to departure from your established design language, and play with the voice and tone of your emails.

…that’s my advice to anyone starting out: always experiment.

BRADLEY: Once we send a new email, like a lot of people I rush to the reporting dashboard and keep my cursor firmly hovered above the reload button (for some reason, more trusty than Command+R), clicking again and again, delighted as the opens roll in.

Sort of like in the Olympics where the highest score in a particular parallel bars routine might top out at a 9.0, we understand that the expectations for each list or campaign are different. Sending an email to 500,000 about a range of new features will have different results from an email targeted by industry. For us, open rate is influenced more by our selected segment than a controlled variable like send time or subject line. With the top-level stats, it’s often more useful to focus on specific clicks — which pieces of content are driving interest — and even unsubscribes.

In addition to monitoring sentiment on social media and tracking installs of promoted features, we can look at effectiveness over a longer period, too. If we send an email about templates, how likely is a reader to try our custom code editor or visit our Email Design Reference? A year later, how has this group used MailChimp compared to those everyone else? Because our sending isn’t connected to an immediate purchase, and with nearly all of our campaigns segmented, we usually look beyond a trend from one email to the next.

What kind of system do you use for mapping the product email roadmap – from customer sign up through to retention email and even a goodbye email?

FABIO: We have a purpose-built directory of our transactional emails, where each one we send is shown according to its category, and the HTML and plain-text versions are displayed. For time-based emails like a new account confirmation and early on-boarding information emails, they’re shown on a timeline along with specific points of information for each message. Emails are also broken down into “no opt”, where something like an order receipt lives, and “opt-in/out” categories, where you can find emails like “campaign sent” notifications. This directory gives us a broad overview of the emails that go out to all of our users, and it’s open within the company, which allows lots of people a chance to get their eyes on these emails, understand their specific purposes, and offer suggestions for improvement.

What advice would you share with others about how to approach their email marketing strategy?

FABIO: For my part, I’ve developed a set of guiding principles that I employ when I design an email.

First is “design within constraints”, which boils down to knowing what you can and can’t do in email clients, then build and design accordingly.

Second is “design for distraction”, which means that emails should be designed to be easily used and usable regardless of the platform on which they’re viewed, while at the same time having a minimal disruptive impact on the reader’s workflow or life.

Third is “design with purpose”; that means you should avoid trying to please all of your subscribers with a massive, all-purpose message, and instead build emails to suit separate audiences that want to buy something or read something. Know how your audience divides itself and then strive to create content that each group wants to see.

BRADLEY: There’s no right way to send emails — no perfect day of week or time of day, no universal subject line, no ideal frequency. Data science helps aggregate results from billions of emails to find places where you might want to start. But what works for one customer might be disastrous for another. The only way to figure out what works for your list is to keep testing.

There’s no right way to send emails — no perfect day of week or time of day, no universal subject line, no ideal frequency.

What is the most effective email you’ve had to date? What do you think made it the most effective?

FABIO: On the transactional side, I don’t think there’s really a singular email that you could call “most effective”; for emails like the timeline-based on-boarding messages, they’re treated more as small building blocks of the larger narrative where we attempt to get a user up and running within MailChimp, and their first campaign sent within a reasonable amount of time. Helping users do that, however, isn’t done solely through email; the emails are just part of the entire start-up process, the majority of which happens in the application itself.

BRADLEY: One standout is our MailChimp’s Newsletters email. We used it as an opportunity to tell some of our customers about additional email content and followed it up by selecting random subscribers to receive vinyl toys of our mascot, Freddie. We made the signup process as seamless as possible, so folks could click to join and an opt-in would deliver automatically without having to refill a form or reenter an address. And we added 17,000 new subscriptions!

Who do you watch and learn from for your email marketing techniques and strategies?

FABIO: I keep an eye on the emails coming from other service-oriented companies, like airbnb, or even retailers, like Amazon. I’m also subscribed to tons and tons of lists for product- and service-providers ranging from small mom-and-pop shops all the way up to big box retailers. I pay attention to how the emails are designed and built, and what sort of content each message carries; retail emails especially are great to keep an eye on for lots of experimentation in design patterns, as companies tweak and tweak to squeeze all they can out of their messages.

BRADLEY: I’ve somehow found my way onto what seems like thousands of lists. Every day, I learn about new features in a product I signed up for years ago. Now that email is a somewhat important part of my job, I try to read every one. While the checkup reminder fired from my dentist’s new CRM is missing fancy animations and catchy copywriting, it’s really valuable to think about each email, what it’s doing, why I might be getting it, and how it fits into the other messaging I’ve received.

Do you have a philosophy that drives the decisions about what goes in an email and what doesn’t make it?

FABIO: I think the overriding philosophy that I follow is, “be human.” With each email, we’re asking people to commit a measure of their time, and we try to be respectful of that. There are some core ideas which I follow, in an attempt to make sure the emails we’re sending are more worthy of a person’s time commitment. As much as we can, we keep emails free of informational bloat, but comprehensive enough that they aren’t thin on value, and we also try to ensure that the emails are easy to get through regardless of the platform (mobile or desktop) or medium (digital or paper) they’re viewed on.

With each email, we’re asking people to commit a measure of their time, and we try to be respectful of that.

BRADLEY: When in doubt, cut it out. This happens to be the same as my high school wall decorating strategy. But, in general, if we have to think too hard about if something should be included, it’ll probably fit better in a future email to a better audience.

Meet Fabio Carneiro, he is one of MailChimp’s email developers, his approach to on-boarding and transactional emails is primarily technical. He’s more concerned with email UX than conversion.

Meet Bradley Gula. He works on the marketing team selecting segments, writing content, running tests, and analyzing results. His job is to figure out who’s least likely to be bothered and to send relevant information at the right time.

This interview by Matthew Smith, AKA @whale, and the Captain on The Fathom & Draft, a treasure hunting ship. He’s also the founder of Really Good Emails, dedicated to showcasing and creating discussion around the best product emails around.