Thinking Outside The Box: 4 Emails You Should Be Sending This Holiday Season

How can you take your emails from good to great this holiday season? Columnist Jimmy Daly says the keys are context and personalization.

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santa-envelope-holiday-retailer-ss-1920While everyone else is working on their next promotional email, why not take a minute to think about sending emails that your customers and subscribers actually want?

During the holidays, most marketers seem to forget that email isn’t about yelling, it’s about listening. Segmenting, for example, is essentially listening: you gather data about people and respond, rather than blasting the same message to everyone. Users respond much better to triggered emails because they have a killer advantage: context.

(Case in point: Transactional emails are opened at up to 8x the rate as promotional emails.)

This isn’t to say that you shouldn’t use promotional email and newsletters to get the word out about a holiday sale, but try to think bigger about your email strategy. Taking advantage of transactional and behavioral emails is the fastest way increase your email ROI and generate more sales.

Here are a few examples that you can use as inspiration this holiday season.

1. Welcome Emails

It’s likely that you’ll see a surge of new customers or signups during the holidays. These people need a killer welcome email. It’s your first opportunity to communicate with them directly. Here are a few tips for great welcome emails:

  1. Get Personal. Don’t send welcome emails from a “[email protected]” address. Send it from the CEO or someone on the support team and be ready to handle replies.
  2. Include A Call-To-Action. Don’t just say hi, tell the person what to do next. And use a button.
  3. Give Something Away. Giveaways don’t always have to be incentives. A kind gesture to a new user might be just they need to complete your onboarding process.

Here are a few examples:


This email is simple, clean and on-brand. The only thing I don’t like is the “from” address ([email protected]).

ello welcome email

Raven Tools

The folks at Raven know that the sooner new customers understand how to use their product, the faster they will find value in it. Getting people started with a course is a great first step.

raven tools welcome email


If you need new users to download an application or file in order to get value from your product, don’t beat around the bush. Sqwiggle does a great job getting new users engaged right from the start.

sqwiggle welcome email

2. Browsing/Cart Abandonment Emails

If you have the ability to track customer behavior on your site, you need to be sending emails based on their actions.

This applies mostly to SaaS businesses, mobile apps and ecommerce sites, but any email marketer can learn a bit about advanced segmentation from these emails. Here are a few tips for great browsing and cart abandonment emails:

  1. Understand Your Customers’ Purchasing Behavior. Where in the process do they need a nudge? If you’ve tracked a customer that’s come via organic search and viewed a product page twice, it’s likely they are ready to buy. Give them a nudge right away.
  2. Offer Alternatives. It’s not always right to give potential customers a “Plan B” but if you understand why they aren’t buying, you can offer them alternatives (a lower priced item, an extended free trial, etc.)
  3. Address The Customer’s Anxiety. If you’ve been tracking a customer that has repeatedly visited your site but not purchased, use email to soothe their worries. Testimonials are a great way to accomplish this.

Here are a few examples:


This is one of the best behavioral emails I’ve ever seen. I explain that in great detail here, but what you really need to know is that it came at just the right time in my decision-making process.



No one does email as well as Amazon because they put their data to good use. (Yes, I was looking at Halloween costumes for my dog. Thanks for that, Amazon.)



The average cart abandonment is 68.06%. That’s a substantial amount of near-misses! Imagine if a simple email could bring those customers back. Target does a good job incentivizing people to come back and complete their purchase by offering coupons with a strict expiration date.


3. Email Receipts

Receipt emails are extremely useful — that’s why people open them at such high rates. The goal here is utility, but that doesn’t mean your receipts shouldn’t move customers toward their next purchase. Here are a few tips for great email receipts:

  1. Use Referral Codes. You send receipts to people who have made a purchase. This is a clear indicator that they like what you have to offer. Use referral codes as an easy way for them to spread the word. Everyone wins.
  2. Show Related Products & Services. If you have accessories or upsells, don’t be afraid to include them in a receipt.
  3. Include Micro Calls-to-Action. Encourage customers to follow you on Facebook, Twitter or Instagram, sign up for your newsletter or check out an upcoming webinar. Small wins like this keep people engaged.

Here are a few examples:

Dollar Shave Club

Dollar Shave Club is like the SaaS of shaving. It’s an ecommerce business with some of the smartest emails you’ll ever see. It’s worth paying $1 per month just to get an inside look at their marketing.

dollar shave club receipt


Uber’s receipts are loaded with context. They include the customer’s name, the driver’s name, a map of the route and the distance and time. And, like Dollar Shave Club, they include a referral opportunity and micro calls-to-action.

uber receipt

Hemingway App

Here’s an example of a welcome email and receipt combined. The information about the transaction is easily available but the real purpose of this email is to get new users to download the software as quickly as possible.

hemingway app receipt

4. Feedback Emails

Why does Amazon ask every customer to rate every product they buy? Because that feedback helps them 1) feature the best products and 2) use their own customers as advocates for those products. Social proof, after all, is one of the most powerful marketing tools.

You’ll notice this post has covered the customer lifecycle in order. Feedback and referrals are the last step. Here are a few tips for sending great feedback emails:

  1. Make It Easy For People To Respond. Don’t ask your customers to fill out a long survey. Identify the data you need and ask them to answer a single question.
  2. Explain The Value. This is your sales pitch. Explain how you plan to use the feedback to help others customers or improve your product.
  3. Use A Call-To-Action. Every email needs a call to action. Explain exactly what you need people to do.

Here are a few examples:


Amazon positions itself as an impartial bystander. It’s almost as if they are saying, “Don’t help us, help your fellow customers.”

amazon review


CrashPlan does a great job explaining why feedback is important not just to them, but to the person filling the survey out. Also, notice the use of a bold, contrasting button.

crashplan survey

Dollar Shave Club

I’m telling you, Dollar Shave Club kills it with email. This is the extent of the feedback. Simply click a button and you’re done.

dollar shave club review

Now you’re ready to crush it this holiday season. Have any questions? Drop them in the comments.

Opinions expressed in this article are those of the guest author and not necessarily MarTech. Staff authors are listed here.

About the author

Jimmy Daly
Jimmy Daly is the marketing director at the content agency Animalz.

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