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S02, E01 | Oct. 13, 2020

Holiday Insights Series: Email Marketing and SMS Strategies


Gabe Macaluso, Director of Customer Success at Omnisend


Omnisend is an ecommerce-tailored email & SMS marketing automation platform built to help nimble teams drive more revenue without increasing their workload.


Ecommerce Marketing

Additional Links / resources

In this episode of the Cart Insiders Podcast, we welcome to the show the Director of Customer Success here at Omnisend, Gabe Macaluso. In his role, Gabe works directly with Omnisend clients helping them improve their marketing programs—including holiday prep. As two veterans in the email marketing space, Gabe and Greg discuss tips and strategies for preparing email and SMS campaigns for the holidays—including their no-bullshit preparation tips.

Gabe starts by discussing when companies should begin their holiday season and overall email send frequency—how often is too often to send—before shifting to the importance of automated messages, especially the welcome. Gabe shares what to watch for with the message content and discount strategy, before diving into how to use SMS to make automated messages all the more effective.

As the conversation pivots to cart and browse abandonment, Gabe shares his insights into utilizing SMS as a ‘nudge’ to remind customers about the products that they are interested in. Greg and Gabe then go deeper into abandoned cart strategies, exploring tips and tactics, and how to use different channels to promote a sense of urgency to customers. They share stories of often-overlooked aspects of holiday cart abandonment and provide some useful tactics for improving those messages.

Shipping is a major theme this holiday season, and Macaluso discusses not only the importance of offering free shipping to customers but the best ways to go about this. This leads to a conversation about the latest trends in online shopping as consumers increasingly go digital in the wake of COVID-19 and the customer retention opportunities it presents. With an expected increase in first-time purchasers, Gabe dives into the cost benefits of turning these shoppers into repeat customers.

“One of my favorite strategies, as we get into the holidays, is how to push people from Facebook or Instagram, where the return on ad spend is minimal, to email and SMS, where ROI is much higher. You can post something on Facebook, for example, saying ‘hey we’re going to drop a huge holiday sale, but the only way you can find out about it is by signing up for our email and SMS.’ This way you’re creating a hyper-targeted, very engaged group of people that are happy to be front of the list for your products, and are happy to engage with you via SMS for personalized messaging.”

It wouldn’t be a holiday conversation unless there was talk around the big days like Black Friday and Cyber Monday. Greg and Gabe discuss whether these stand-alone days should be largely ignored this year, and how the Cyber Ten, Black Friday Week, and Gray November will impact them. Gabe then shares his advice for email send cadence on these high-volume days, how to build excitement for big deals, and when SMS may be the most effective communication channel for brands.

Greg and Gabe end by offering their one, no bullshit piece of advice for preparing for the holidays. Listen to the entire conversation for all of this and more.

Main Discussion Points

  • Email frequency during the holidays—how often should you send emails to your customers—and the types of messages that are vital to set up for the holiday season.
  • Omnichannel messaging and automation. We discuss utilizing SMS in automation, abandoned cart strategies, and ways to incorporate omnichannel messaging to create a sense of urgency.
  • How much of an effect will free shipping play? We discuss the actual importance of offering a free shipping option for all customers and the best ways to go about this. We also hear about the latest trends in online shopping, as more and more customers go digital in the time of COVID-19.
  • The best scenarios to utilize SMS. We discuss at which times SMS is a more effective communication channel, highlight these opportunities, and explore the best ways to get your messages across.
  • Black Friday and Cyber Monday. We discuss the busiest days and how important they actually are, shipping issues, and things to start preparing for right now. Gabe shares his insights into timing and ways to increase send cadence to grow a sense of excitement and anticipation for the big deals to come.
  • Finally, Gabe and Greg share their one, no BS thing that every marketer should do this holiday season.

Listen to the full story on the Cart Insiders Podcast on Apple Podcasts, Google Podcasts, Spotify, or wherever you listen to podcasts.