The welcome email. The re-engagement series.The abandoned cart rescue stream. Triggered email is an essential aspect of any reputable brand’s email marketing arsenal.

So why is it that triggered email is often the least talked-about, most undervalued email tool in a marketer’s arsenal? In fact, during the research of Sailthru’s Personalization Index, we found that triggered email strategies are some of the areas where the world’s biggest brands are underperforming.

But with sky-high engagement rates, triggered email is one of your best opportunities for building trust, loyalty and further engagement with your consumers in a single message. Even the best campaigns would be hard-pressed to do the same.

But some marketers out there do love getting their triggered email on. Jessica Sirizzotti, the Director of Content Strategy and Engagement at financial company PayPerks, is one of those smart marketers using triggered email to grow the company and be customer-first.

We recently caught up with Jess to talk all-things triggered email — read on for the full Q&A where we discuss why it’s so valuable, what to test and more.

SAILTHRU: Jess, tell us a bit about yourself, your background and your current role.

JESSICA SIRIZZOTTI: In reverse order: I work at PayPerks, a financial literacy and rewards program for underbanked consumers. We help people who don’t use bank accounts navigate their financial options, with monthly cash prize drawings to keep people engaged.

I’m the Director of Content Strategy & Engagement, which means I write the tutorials on our site and encourage people to take them through Sailthru email campaigns, site promotions, social media, etc.

Since I don’t come from a finance background, I have a healthy appreciation for how difficult personal finance is to learn from the ground-up. It’s scary! And the stakes are very real, so there’s a lot of pressure to get it right.


Many marketers overlook triggered email. Why do you find it so valuable?  

Triggered emails are such an important foundation for your communications engine.

By automating the small stuff, you build a rapport with your members. They know that they can count on the routine of a consistent touch-point—whether it’s a monthly summary of their progress, a reminder to buy items from their shopping cart, or something else that sets your company mission apart.

Knowing that we have a robust system of recurring triggered emails gives us the bandwidth to devote development time to campaigns that introduce new information. That way we know new members get a consistent onboarding or re-engagement experience and we’re not trying to solve every edge case in a single campaign.


How is PayPerks using triggered email today?

In addition to the basic welcome and reset passwords emails, we also use automated emails for onboarding. Currently we’re using:

  • Welcome: immediately after signing up, we send a brand reminder with some “getting started” tips
  • Outreach from Founder: covers the mission of PayPerks, how we hope to help our new member, and a favorite tutorial
  • E-Scratchers: our members love the Scratcher Codes we send out in the mail, and this electronic version welcomes them to the site
  • Help Center: introduces our approachable Card Info pages, site FAQ, and our customer service team
  • First sweepstakes: a few days before their first drawing, we send a primer on how they work, when they can expect to be notified about prizes, and a final opportunity to earn some chances to win!
  • Second sweepstakes: our last touchpoint with members before we consider them fully onboarded reiterates the sweepstakes flow and points them to a benchmark survey they can complete for more chances to win

Our program isn’t very complicated, but it is helpful to have a couple specific spotlights over a few weeks to break it down for new members. It’s been really successful, and we did a lot of testing before we settled on our current version. We’re in the process of moving it over to Sailthru’s new Lifecycle Optimizer and I’m excited about leveraging the testing capabilities there. It’ll be great to test template designs, subject lines, and rollout windows without needing to do a tech release to start and stop.


Have you ever re-evaluated your triggered email program? What prompted the reinvention?

We have. We add new card programs to our platform periodically, and each audience is a little bit different than the ones we’ve met before. So we update links, logos, and messaging (everything necessary for launch) and then monitor for about a month. Then, whether it’s performing as expected or not, we tweak something and test it.

This can be a great team-building exercise. Everyone on our team receives different emails, so we try to foster a culture of friendly forwarding for designs or subject lines we found compelling (or poorly executed). Since most of the email design is handled by me and our designers, it’s great to stick a campaign on the projector during team lunch or a free 10 minutes at the end of a meeting and get other perspectives.

A good way I’ve found to get testing-averse teams to loosen up is to do mini contests for subject lines. Marigold Engage by Sailthru’s A/B testing makes it so easy to try different subject lines with campaigns, and you can do one week tests for triggered emails too. Have people submit suggestions and the winner gets a treat or a badge on their desk!

Having testing frameworks and pre-scheduled check-ins like that helps avoid the inertia of “if it ain’t broke, don’t fix it.” Otherwise, you might forget to look in on a triggered email for years, losing track of your brand in the process. Set a calendar reminder for once a quarter, and see what difference a few months makes when you look at that “perfect” email.


Can you share any specific success stories or even failures that you’ve learned from?

One of the most important things I’ve learned is that you must think a few goals ahead of what’s directly in front of you.

Just as not every email has the same CTA, not every measure of success is a click-through.

We had a card program with very high open rates but extremely low conversion. Since our goal is to educate cardholders on financial topics, we simply started including the tips and suggestions in the body of the email. No need to log in!

Much like Amazon does by including all the shipment information the subject line of their order confirmation emails, we surfaced the need-to-know information to where members were looking, rather than trying to shoehorn them into our preferred workflow. It takes a customer-first approach (and a cohesive company goal structure) to feel secure in trading an easy excuse for a click-through in favor of long-term “they make it easy for me to get the info I need” brand loyalty.

Twitter does the opposite with regular “click here to see your notifications” emails, so it’s all about what kind of message your audience is receptive to.


How are you testing triggered emails? In what ways do you think you have improved or can improve?

As I mentioned earlier, supporting an extremely wide range of devices and browsers is part of our brand promise. PayPerks is all about providing access to people who are often told it’s too inconvenient to meet their needs, and we never want someone to feel like that with our site or emails. So anytime we want to incorporate a new feature, whether it’s a div bounded button or an auto-scroll, we test it on every device in our arsenal as well as the Web Accessibility Checklist from The A11Y Project.

This focus on accessibility hasn’t shortchanged our creativity or even dramatically impacted our testing timeline. Once you figure out what systems your members use and build the tests for them, it’s perfectly scalable to build that into the email building workflow.

On a more qualitative level, we’ve tested:

  • Long-form vs. short-form styles
  • Button color and text
  • Flat UI vs. gradients
  • Text only vs. bright images
  • Hand illustrations vs. stock images
  • Inline links vs. plain text
  • 2 month vs. 2 week onboarding window

Anything’s up for testing, and the only consistent conclusion I’ve found is that every audience is different! Our members constantly surprise me with their preferences, so testing is crucial to ensure my own biases don’t lead us by a missed opportunity.


Which brands do you think are killing it with email? Why?

Anyone who supports opt-downs instead of opt-outs! Subscription preferences are huge for any brand using email marketing. Giving power back to the consumer to decide when and how they want to receive email from a brand is ultimately the best experience you can provide. That way you can ensure that when you are emailing your audience, they actually want to hear from you!