We strive to find the people in our industry who have something worth sharing. We’re curious about email because we believe it’s the most used product on earth, and it’s the channel that more businesses grow by than any other. Yet, it can be annoying to use, get, and send. That’s why we’re exposing the best of the best and curating a great collection on ReallyGoodEmails.com — when we’re not interviewing the giants.

It sounds like you’ve been doing Square emails for a while now. What’s one thing you thought you knew at the beginning that you now understand differently?

With a few years of experience in email development, I thought I was pretty quick at writing code by hand and using snippets in Coda. After being introduced to task runners (like Grunt) and myriad other tools, I realized that automation can enable a much greater volume of work, and I can build emails faster with little to no errors.

How are you balancing Square’s super-tight brand with the need for these emails to perform well, aid in growth, and service existing customers?

At Square, it’s easy to present many variations of our emails for internal review with our flexible library of design patterns and styles informed by our public website. Our aesthetic lends well to simple, powerful messages, enabling us to experiment with content and find combinations that appeal most to customers.

We’ve made a strong push to elevate the value of images we include, removing those that don’t provide context or value. We want every aspect of our emails to be helpful, so customers can quickly get the information they need and use it to benefit their business.

Can you share one or two examples of small changes that you have tested in your emails that made a significant impact on retention, click-through, or service to Square customers?

Previously, we sent a single reminder email 10 minutes after signup to people who hadn’t finished activating their Square account. People are busy (especially business owners) and sometimes need multiple nudges. Currently, we send reminders one, three, and seven days after signup. In each reminder email, we share simple tips for starting and running a business on Square. As a result, we’ve seen a huge spike in activations and improved our seller education.

We also integrate personalized messaging when emailing sellers with account-related information. We found that any specific data included beyond the recipient’s name nets significant gains in open rate and engagement with the links, and helps sellers understand the value of tools available to them. Examples include using the dollar amount we can offer sellers with capital, the number of customers that sellers can reach with Square Customer Engagement — our CRM software — and specific transaction data in support messaging requiring action from sellers.

What’s the effect of the smile / frown opportunity in transactional emails on receipts?

We want to give sellers a simple way to solicit feedback from their customers. A star rating makes sense in a quantitative setting, but we were more concerned with giving sellers qualitative feedback from their customers. We settled on smiley/frowny face so sellers could track feedback (e.g., 90% of customers are happy this week), and get detailed responses. Once a customer chooses a face, they’re prompted to leave written feedback about their experience.

What’s one problem you’re currently trying to solve?

We’re currently auditing every email we send to sellers to identify discrepancies in messaging and designs. We’re working on new design templates and are using this exercise to unify our messaging and ensure we’re consistently on brand.

Examples

Onboarding: Accept your first payment For sellers who haven’t taken a payment within 3 days after activating. This is an example of a Square Register-related message, which makes use of actionable modules.