Playbook: Creating End of Year Emails

How to end the year wowing customers and getting the attention of execs.

Why send end of year emails?

With budgets becoming more stringent, tech stacks are being slashed, and no tool is safe from rigorous scrutiny. And when a decision maker asks why the company even needs this product, you have to be ready to clearly quantify the impact of your product.

But why wait for that question to be asked? Why wait for that next business review (the one you’re hoping that an executive will attend)? Or even worse, why wait till renewal?

It’s close to the end of the year, aka the season of Spotify Wrapped. Everyone loves to learn more about their music taste and more importantly, what other similar music they uncover.

And there’s no reason why you can’t bring that same joy to your customers. An end of year email is a powerful way to showcase your product’s value in a way that’s highly specific to your individual customers. And a good end of year email is known to get the attention of executives.

This playbook will walk you through the whole process of executing an end of year email campaign, from ideation to the sending to all your customers (big and small).
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Hyper-personalization

There’s a concept you’ll see repeated throughout this playbook and it’s key to making your end of year email successful: hyper-personalization.

Hyper-personalization is when you customize content beyond just segment-level information, and tailor it based on customer-specific data. In today’s communication-saturated environment, it’s how you make any content you’re sharing with customers standout and keep their attention.

The best way to understand hyper-personalization is to contrast it with superficial personalization, the type we see happening everywhere. For example, when you see an email that goes “Hi [your name], I see you work at [company name]. In [industry], we see a lot of customers use [list of features],” you’re probably not impressed. That’s because you know that they’ve blasted this same email (minus the name) to many others. While there may be a tid-bit or two that you find useful, you’re more likely to hit delete.

And hitting delete is exactly what your customers are doing too.

But how much more impactful is an email that says, “Hi [your name], Your team at[company name] has been using [top feature] a lot and been seeing [ROI value] from it.Based on your goal of [business outcome], we recommend also using [specific feature].Happy to [specific next step] to help your team.”

Hyper-personalization, it does the customer good.
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The Playbook Steps

Creating an end of year email consists of four major steps. Now before you think that we are oversimplifying, don’t worry we are not. There’s definitely a lot happening in each step, and we’ll dive into the specifics.

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    Define the who & why

    Get alignment on why it’s worth while to run this campaign & get access to resources

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    Creating the email content

    Bridge the gap between the ideal and what is actually possible

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    Launching the email

    Make it happen!

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    After the launch

    Learn & take it to the next level

Define the Who & Why

Get alignment on why it's worthwhile to run this campaign and get access to resources.

  1. Identify who to send to
  2. Figure out the 'why' for them
  3. Define success
  4. Get buy-in

All good emails (and content) start with the customer in mind. It’s easy to fall into the trap of thinking this email is for your company. But the goal here is to make sure that the customer is getting value from it (which isn’t at odds with your company getting value from sending it).

Identify who to send to

As you’re thinking through this, you’ll want to consider the various segments.

Woah, segments - doesn’t that go against hyper-personalization? Only if you stop there. Think of segments as the first step to hyper-personalization. By defining the segments, you’ll have an initial idea of how the emails may vary.

Potential segmentation:

  • Product lines used by the customer
  • Company size
  • Company industry
  • Geography
  • Business model
  • Team
  • Role
  • Use case

Figure out the why for them

This step will help you clearly define the value of the email to the customer. For each segment, answer these two questions:

  1. What do you want them to take away from the email?
  2. What do you want them to do after seeing the email?

Define success

Defining success will help you identify your north star for this email campaign, and give you a structure for making decisions. And there’s a lot of decisions that will need to be made. Make sure to think both tactical and strategic.

Tactical

These are metrics that are around general email performance. They’re important to keep an eye on to understand if the email “worked.”

  • Open rate - The percentage of recipients who opened the email out of total recipients.
  • Click through rate - The percentage of recipients who click on a link in the email out of the total recipients who opened the email.
  • Unsubscribe rate - The percentage of recipients who opt-out from receiving further emails from you out of the total recipients.
  • Bounce rate - The percentage of emails in your recipient list that didn't receive your email because it was returned by a recipient mail server.
  • Spam complaint rate - The percentage of recipients who reported your email as spam out of total recipients.

Strategic

These are the metrics that will help you get buy-in company-wide to do this email, and ultimately help you decide if you should do it again next year. An end of year email requires a lot of lift from a different departments, so make sure you’re always coming back to what will move the needle for the company. Check out examples of strategy metrics below.

  • Product Usage - The number of recipients who increased usage of the product (can also be segmented by those who used a feature for the first time, general usage increase, or even users who started using the product in general, or began using it again)
  • Renewal Rate - The percentage of accounts who went on to renew
  • Expansion Rate - The percentage of accounts who went on to expand through upsell or cross-sell
  • NRR - The percentage of revenue retained from existing customers over a specific period of time, typically a year

Get buy-in

End of year emails are notorious for requiring a lot of help from many departments. So, how do you get buy-in? By leveraging the success metrics and providing an estimated impact, you’ll be able to inform prioritization and how much resources to lend to the email. Specifically, you’ll want to lean on the strategic metrics (because no one cares about how many people opened an email). End of year emails have the added benefit of providing a fun, rallying point for a company. So for those who haven’t yet run a hyper-personalized campaign like this before, it can be a great starting point.

Who you'll need buy-in from:

Customer Success

Help determine segmentation and recommended next steps

Marketing

Help inform email strategy and content

Design

Help make the email easy to understand visually and eye-catching

Revenue or marketing operations

Help implement personalization and bringing the data into the email

Data analytics

Help figure out what data should be used in the email

Creating the Email Content

Bridge the gap between the ideal and what is actually possible

  1. Ideate on best case
  2. Align on the real version
  3. Implement best practices
  4. Determine A/B tests

Let’s be clear, what you dream of in this step is not what you’ll end up sending. But you’ve got to start somewhere! Here are things to keep in mind:

Focus on the customer & what they care about

Revisit your answers in the “Figure out the why for them” step to determine what you need to include in the email. And ALWAYS tie it back to THEIR business outcomes.

Take inspiration from your existing content

Content like business review decks, renewal decks and ROI analyses are a good jumping off point for understanding what data is already available.

Don’t be “basic” with your data

Matik's Hierarchy of Data

Using very simple data can lead to a “well, duh” moment instead of a “oh, wow” one. A good framework for thinking about what data you want to share is Matik’s Hierarchy of Data (similar to Maslow’s Hierarchy of Needs). At the bottom is your account data, which is straightforward information like what is included in the contract. Usage data is much better than account data and helps the customer understand that they are getting something out of your product. But ROI, the most transcendent of data, is what helps you customer connect the dots regarding why your product is critical to their business.

Always be recommending

Showing customers the ROI they’re getting today is cool, but showing customers the additional ROI they could be getting if they did X and Y makes you a trusted advisor to them. Guide them to what more they should be doing with your product (even if it means they need to pay more) by showing them how it can impact their business.


Example of Metrics

Figuring out which metrics to highlight can be one of the more difficult aspects of creating an end of year email. How do you create something compelling. Below are examples of what a few B2B tech companies might use in their end of year emails.

Align on the real version

Expect this to be a collaborative process with all of the stakeholders. There will be a lot of back and forth, and that’s a good thing!

Ensure a smooth process by:

  • Starting the project as early as possible
  • Understanding the technical limitations of the email platform
  • Understanding the technical limitations on the data side
  • Not trying to automate everything, at least the first time
  • Expecting not to get all the bells and whistles the first time around
  • Creating a list of what doesn’t make the cut for future iterations
  • Determining whether something is necessary by asking if it will move the needle on the strategic goals

Implement best practices

Best practices for emails

Improve open rate

Try this...Subject line: Create an eye-catching subject line that is clear and understandable; verbs and action-oriented language can create excitementPreview text: Leverage preview text to further entice the recipient to open the emailFrom line: Send emails from a real person versus a generic company email

Improve click through rate

Try this...Hyper-personalization: Include data & recommendations personalized to that specific customerCall-to-action: Create a compelling call-to-action & minimize the number of CTAs in the emailEmail design: Use a clear, uncluttered design with easily clickable buttons or linksConcise copy: Make it easy for a recipient to easily scan the email

Unsubscribe rate

Try this...Hyper-personalization: Include data & recommendations personalized to that specific customer

Spam complaint rate

Try this...Unsubscribe: Make it easy to unsubscribe

Bounce rate

Try this...Email list: Clean up your email list, including removing deactivated users

Determine A/B Tests

Can't agree on something or unsure if it will work? Then A/B test!

Choosing the right data visualization

While not a standard email best practice, if you plan on including a data visualization like a table or a chart, then it's important you pick the right. The wrong data visualization can lead to more confusion, and instead of customers getting excited, it'll lead to aggravation. Use the below flow chart to determine which data visualization is the best for what you're trying to communicate.

Launching the Email

Make it happen!

  1. Determine timing
  2. Get data ready
  3. Prep email platform
  4. Track metrics
  5. Test
  6. Enable/train

Determine timing

Timing is everything for an end of year email. Once you decide your send date, make sure to create a workback plan from that date so you know what milestones you need to hit and when.
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Get data ready

This is arguably one of the most challenging parts of creating and sending an end of year email. But since the data is the heart of the email, it’s a step you can’t afford to skip.

Figure out what data you’re getting & from where

Data at most companies lives in a lot of different places. Once you’ve determined what metrics you want in the “Creating the Email Content” step, you need to have an understanding of where it might exist.
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Lock in filters for the data

You’ll want to consider the following as you determine parameters for the data:

  • When will you pull the data for the send & how recent will the data be at that time?
  • Is there any “bad data” that you’ll want to exclude, like false positives, tests, etc.?
  • Are you going to pull on the account level or on the user level (that’ll vary based on the seniority of the recipient)?

Run spot checks

Before using the data in the email, make sure to do a spot check with your customer success managers (CSMs):

  • Pull the data into a spreadsheet
  • Ask CSMs to look at data for their accounts
  • Have them flag any inaccuracies, and any data that might not reflect well in the email (ex. low usage)

If data does not reflect well, that's not a bad thing! This is when recommendations are more important than ever and can help turn things around.

Prep email platform

Now that you’re data is ready, it’s time to prep the email. Here’s what to consider:

How are you getting the data in?

Generally you’ll have two options: bulk upload and syncing.

  • Bulk upload is great for a one-time send and can be done by csv.
  • Syncing is the ideal option as it allows you to use the most up-to-date data, and also sets you up for more frequent sends in the future.
  • Syncing is likely to require an integration.

Regardless of which method you choose, you will still need to set up fields in the CRM for each data field you upload, which you will then add to the email as a merge tag.

Merge tags are placeholders (aka variables) that you’ll type into the email to let the platform know where it should insert the field value for a customer.

How are you delivering the email?

The goal here is to optimize for engagement. Use previous email sends to optimize for engagement.

  • Pick a day and time that is deemed optimal based on previous email sends. Many email platforms offer the option to send in the recipient’s time zone. For example, if you pick 7 am, it’ll send at 7 am PT to those who live in that time zone.
  • Decide who the email will come from. Ideally, it should come from your front line, i.e. customer success managers. But if you are unable to set it up this way with your email platform, then a general email address will work. Make sure to edit the From Name field to something that highlights it’s from your company (ex. Matik Team instead of just Support).

How are you dev'ing the email up in the platform?

If your designer is HTML savvy, then lean on them to convert the email design into the platform. If not, there are many vendors who’ll convert your email design to HTML for a reasonable fee. You would then take the file they created and upload it to the email platform.

Bonus ways to make your email stand out:

  • Add a table or chart - This will require some creativity to “fake” a table or chart, as email platforms don’t support sending personalized tables and charts at scale. One way to do this is create a static grid or a static chart and have the merge tags placed within them to make them seem personalized.
  • Attach a personalized PDF - There’s only so much you can do in an email without overloading the customer. To dive deeper, create a PDF attachment with personalized content, including tables and charts.

Track Metrics

All those success metrics you defined in the “Define the Who & Why” step - make sure you can actually track them!

Email metric tracking

This is standard in all email platforms, so nothing to check here.

Product usage tracking

Many companies using a tool specifically for product analytics. Check with your product or engineering team that the features you are recommending are being tracked correctly.

Connecting email activity to product usage

Some product analytics platforms will integrate with your email platform so that you can pull email, send and open data into the product analytics platform. This will make it even easier to track the impact of the email, since you’ll be able to create a funnel of both the email and product events. 
If this is not an option, you will manually have to pull the data from each platform and combine in a spreadsheet for analysis.

Renewal and expansion tracking

While the renewal date may be far off, you’ll want to make sure that your CRM tracks which contacts are receiving this email. This can be done through activity records or as a campaign. That way, when you are trying to figure out if you should send another end of year email, you can see how many opportunities were influenced by it.

Test

Most people think when it comes to the testing change, you really can’t make changes. That’s not true - in fact, these might be some of your most critical changes.

There are two groups of people you should get feedback from:

Customer success managers

Customer success managers. Not only do you want to run a technical email test with them, to make sure everything is coming through correctly, but you’ll also want to get feedback on the content.

Trusted customers or customer advisory board

Hear directly from the people you want to engage, and ge their thoughts on the content you are planning to send.

Ideally you aren’t building this content in a vacuum and are looping these two groups in from the beginning. But if you haven’t, it’s never too late to get their feedback and incorporate it.

Enablement

Before you send the email, make sure that both your customer success and sales teams are prepared. This includes:

  1. Training them to be able to speak to the metrics
  2. Coordinating post-send outreach, including how to respond to customers replying to the email

After the Launch

Learn and take it to the next level

  1. Get learnings
  2. Crawl / walk / run

Get learnings

Now that you’ve sent the email, it’s time to determine if it worked! Consider these questions when deciding if your email was a success:

  • How did email perform on a tactical level?
  • What was the impact of the campaign on a strategic level?
  • For tactical and strategic metrics that it did well on, why do you think it worked?
  • For tactical and strategic metrics that it didn’t do well on, why do you think it didn’t work?
  • How did customers respond to the email?
  • What were some of the email responses?
  • Did anyone mention it in other channels?
  • When you ask select customers in your next meeting what they thought of it, what did they say?
  • Did anyone mention it in other channels?
  • What did they think of the content in the email?
  • Did it start any conversations internally?

Remember: Even if the email isn’t wildly successful, you can take the learnings to make the next campaign much better!

Crawl vs. walk vs. run

Now that you know what works & what doesn’t, the next step is determining what to do next. The big question to answer is how often do you want to send a campaign like this that showcases your product’s ROI and recommendations for getting more out of it?
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‍The Checklist

Don't miss a step. Download The Checklist to use with your End of Year Email.

Creating your own with AI

There's no reason to start from scratch when you can use AI to give you an initial stab. And don't worry, it's free.

  1. Go to the end of year email creator & click "Create my email"
  2. Provide your name, company website, and company name
  3. Create your free Matik account to access the template library
  4. Review email branding & updated as needed (can do this later)
  5. Download the HTML to send through any email platform or send it using Matik Mail
Click green button to go to end of year email creator

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Uplevel your end of year email with Matik Mail

It gives you everything other email platforms offer AND...

  • Easily connect to BI tools, CRMs, data warehouses, and spreadsheets
  • Send personalized PDF attachments to stand out and dive deeper
  • Use if-then logic to hyper-personalize email content and PDF attachment
  • Create personalized images, text, tables, charts, and AI-powered insights
Green request a demo button