Welcome back to SharpSpring’s Holiday Email Sending Preparation series. With November and December seeing the highest volumes of email sent around the world each year, it’s no secret holiday campaigns are often the bread and butter of a company’s sales efforts. Email practices of holidays past will not get you into the inbox in 2019. With SharpSpring’s full suite of marketing automation tools and our expert email guidance, this year could be your best holiday campaign yet.

In the first part of this series, we focused on ways to solve and prevent delivery issues to make way for building and sustaining a positive sender reputation so this year’s holiday mail will experience positive deliverability (i.e., getting more mail to the inbox. specifically).

Haven’t started preparing for the holiday season? Don’t worry! Head back to the first part of this series and work through the steps before picking back up here.

By now you’re sleigh-in’ your holiday prep if you’ve followed our gameplan. You’ve set up DKIM and DMARC, removed known problematic email addresses (role addresses, disposable, invalids, etc) from your mailing lists, and implemented Confirmed Opt-In (AKA Double Opt-In). That may seem like a lot of steps to take for a few days of sending, but each step will make it more likely for your mail to send without any issues this holiday season.

Can you imagine a holiday season without any email emergencies or catastrophes? Coworkers pass your desk to see you enjoying hot chocolate while smiling at your high open rates. Last year’s resting-Grinch-face resulting from late nights of pulling your hair out over open rates is a thing of the past.

For some, the goal of a joyful holiday email season may seem out of reach, but don’t fret! All of our customers can truly enjoy the busiest email season of the year. You just need to believe… and prepare.

So now that you’ve taken the first steps on your path to the inbox this holiday season, you may be wondering what’s next. Today we’re going to focus on steps to maintain or build a positive sender reputation with ISPs throughout the holiday season (and all year round). ISPs gauge the quality of mail being sent over time to know if mail should be delivered to the recipient’s inbox, to the spam folder, or whether to reject delivery altogether. Since your recipient cannot open and click an email that they can’t see, it’s imperative to take steps to aim for delivery to their inbox.

If you already have a positive sender reputation, congrats! But don’t close this tab just yet! Once you have a positive sender reputation it’s extremely important to take steps to maintain that status—especially during the holidays when a higher volume of email is sent all around the globe.

Deliverability (getting mail to the inbox) is primarily based around your company’s domain reputation. SharpSpring’s sending infrastructure is designed to help boost your ability to get to the inbox, but building and maintaining a positive sender reputation for your domain is instrumental in getting mail to the inbox.

To build and maintain a positive sender reputation we’re going to guide you through the importance of reengagement and reconfirmation campaigns, list segmentation, email frequency, and content personalization. These steps will help you make sure you’re sending relevant and engaging emails to recipients who truly want to engage with your mail—exactly what ISPs want to see to deliver your mail to the inbox.

Recipients, Volume, and Personalization in Holiday Email Sending


  • Re-Engagement Email – Regain interest in your mail among your less than engaged recipients to make sure they will be ready to open and click this year’s holiday mail. Consider your own inbox—which brands have “won” you back into their shopping carts with a great “win back” or re-engagement campaign?
    • Pro-Tip: Including incentives in emails are often a good re-engagement tactic.
  • Re-confirming Lists – After completing your re-engagement campaign and before starting your holiday campaign, you will want to make sure you are only emailing recipients who still genuinely wish to receive your mail. The re-engagement campaign would have started previously unengaged contacts engaging again, so you can send the reconfirmation email to those recipients who have not shown any recent engagement and give them one last chance to show interest before unsubscribing them. Why unsubscribe? Letting go of contacts not engaging is best practice and can boost your sender reputation, resulting in more mail getting delivered to the inbox.


  • Grow your volume over time to prevent overwhelming ISPs with spammy “blast” behavior. Whether you’re new to SharpSpring or you’re expecting to triple or quadruple your volume over the holidays, now is the time to start growing that volume. (A perfect time for re-engagement campaigns!)
    • Unsure what volume growth schedule is best for your mail? Reach out to SharpSpring’s email experts at policy@sharpspring.com for assistance.


  • Segment your mailing lists to strategically target similar recipient groups
    • Engagement – most engaged with your mail to least engaged.
    • Recent opens
    • Sign-ups/form submissions
    • Interests
  • Behavior (site visits, clicking specific links, etc) – Slow down your mail sends to less engaged contacts to give them a chance to catch up and not overwhelm them.
  • Modify email content based on the recipients level of engagement.
  • Use dynamic content to personalize your emails for each individual recipient

All of these items help senders build and maintain a positive sender reputation with ISPs. It’s that positive sender reputation that encourages ISPs to deliver your mail to your recipient’s inbox.

Check out the other posts in our holiday preparation series…

1. Authentication and Delivery

3. Design, Testing, Sending and Monitoring Results

  • Plan out the types of emails you’ll send over the holidays.
  • Test, test, test and then test again!
  • Holiday sending schedules
  • After the send… Monitoring results
Jessica Kaplan