How To Use Personalization To Sell More This Black Friday

By Brennan Dunn

There are plenty of really great articles online that cover the ins-and-outs of Black Friday / Cyber Monday promotions.

While many of these articles are excellent, I haven't read many that really dig into segmentation and personalization, so I wanted to put together a guide that outlines in detail how I've been personalizing my Black Friday campaigns over the last 5 years or so.

I don't pretend that I have it all figured it out or that the way I've done it is the best way, but I do think there are a few things I've been doing – specifically around segmentation and personalization – that have been a huge boon for the business that I don't see covered much in the usual "Ultimate Black Friday" guides.

"Help them pick from all the options in their face"

The other day, Justin Brook posted the following – and I really like what he had to say:

What he's getting at is at the heart of personalization done right.

Personalization isn't just sticking known data, like a person's name or the company they work at, in an email or on a web page.

Personalization is curation. It's positioning. It's shaping a message, or series of messages, to make the most sense to the person on the receiving end.

"People go to the Internet [or, I'd add, join your email list] because they want you to help them decide what to buy, not to just offer more decisions."

Why I think my Black Friday campaigns have done so well over the years is because with each passing year my emails become more personal.

Not only do I recommend specific products people should buy...

But I describe the products different depending on their segmentation.

Fortunately, this isn't all that difficult to do. And, chances are, you're already using the tools you need to make it happen. Let's look at a few different ways that you can help your readers decide what they should buy and why they should buy it this holiday season – rather than just shock-and-awe'ing them with everything you have to offer.

Here's a quick overview of what I'll cover in this guide:

  1. First, you'll survey your audience and determine what their new year's goals
  2. Then you'll send your list through an Offer Funnel, which will surface a recommended product based on their needs and purchase history
  3. You'll then use your survey data to redescribe what you have on offer to make it individually more relevant to each buyer
  4. Finally, the emails you send will highly a recommended product, reducing decision paralysis

Step #1: Find out next year's goals in advance

Black Friday and Cyber Monday happen to fall about a month before the end of the year. Besides carols and lights, what else is happening around then? New year's resolutions get made.

Despite how effective or not new year's resolutions are, people still come up with them.

We're all generally optimistic with the start of the new year, and this excitement culminates when clock strikes midnight on December 31st.

So why not help people see that you want to help them achieve their goals?

In this first step, we're going to ask people how they want to be better/different in the upcoming year, and then we'll use this segmentation data to show people exactly how what you have to offer will help them do exactly that.

A few weeks (or even months) before your holiday promotion, start including self-segmentation links in your emails. For example:

"2020 is just a few weeks away. How can I help you become a better email marketer next year? (choose one)"

  • I want to offer email marketing and automation services to my clients
  • I'm looking for a solid understanding of where to start with setting up automation
  • I'd like to work less by systematizing how I'm currently nurturing and selling to my audience
  • I want to improve cash flow by automating my pitch emails

This question and these answers make sense if you're selling to an audience of marketers, but no matter your business you should be able to come up with new year goal ideas.

For example:

  • Fitness business: lose weight, gain muscle, improve flexibility
  • Teaching people to code: learn the basics, get a new job, get a promotion
  • Invoicing/proposal software: evening out cashflow, closing more proposals, finding more clients

Once you've come up with the question and possible answers (limit to 3-4) that you want to ask your audience, the next step is to actually get this info from your subscribers and attach it to their record in your email marketing database. This is going to unlock ridiculously helpful promotional emails for you.

There are a few ways to easily get some "what do you want to achieve next year?" data:

Trigger links

Most email marketing platforms let you have some way of segmenting someone based on a clicked link. By adding in some emphasized text followed by a bulleted list of answers, with each answer being a trigger link, you can easily create a quick "choose one"-style survey in the emails you send.

Whether as a dedicated email or as a callout in a newsletter, you can quickly and easily segment people based on their new year's goals.

Assuming you can exclude people who are already segmented from a dedicated segmentation email campaign (definitely doable) or conditionally hide your trigger link survey in a newsletter (if-fy, some email platforms don't allow for this), you should be getting anywhere from 20-50% of engaged readers segmenting themselves.


Many of our customers set up segmentation funnels a few weeks (or even months) before a promo to passively collect resolution data when their subscribers are on their website.

Here's how, who I showcase later in this guide, segment visitors when they're on their website. And because RightMessage already knows when someone has already answered a question, once this data is captured RightMessage stops asking on the website and you'll also stop asking people over email.


    If you're struggling to figure out what these different answer options might be, check out our in-depth guide to coming up with a segmentation strategy. This will help you use open-ended surveys to come up with concise lists.

    Step #2: Create an "Offer Funnel" that figures out what someone should buy from you

    Once you're collecting individual segment data about what someone wants to achieve next year, the next step is to combine that with a specific product or offer that they should buy.

    Remember what Justin said above?

    "Pro = Help them pick from all the options in their face"

    That's what we want to do here, especially if you have a number of different products or services available.

    First, we need to figure out what this funnel will look like.

    Here's what we're going to do. It's really simple: Based on what someone's already bought from you and what they told you their goal is... if they could only buy one thing from you, what would that be?

    (If you only have one thing to offer, like becoming a customer of your software-as-a-service company, then this might seem overkill. But I'd encourage you to potentially think a bit deeper. Shouldn't a non-customer email subscriber be offered a trial, and a monthly customer be offered to upgrade to annual? Or to jump to a higher plan?)

    Let's look at, a fitness brand that has four publicly available programs for sale:

    • Elements: foundational
    • Focused Flexibility: helps with flexibility
    • Vitamin: improves balance, agility, and control
    • Integral Strength: increases strength

    I'm not sure if they plan on having a holiday promotion, but let's say they're planning on it.

    They could email their entire list and say "get XX% off every one of our programs!"

    ...Or they could send a targeted promotion that instead says:

    "Hey! Our top programs are on sale today, but this is what we think you should buy to improve your flexibility in 2020."

    The end result might be the same.

    Same courses, same discounts. But by telling someone "You should buy X because of Y, and here's why..." you help them overcome the that accompanies too much choice.

    Instead of the reader needing to read through and think, "I like GMB, but I'm not sure if I need Vitamin... or Elements... or, or..."

    You're instead telling them what you think they should buy from you, which makes all the difference.

    But what if, when surveying, they chose that they want to be more flexible, but they already own the Focused Flexibility program that you want to give people who have that need?

    Easy! Then you just give them something else they don't own yet.

    It doesn't need to be perfect. You don't need to think, "If they want flexibility and they bought Focused Flexibility, what should someone do next...?"

    It can be as simple as just having a single product recommendation per end of year goal, and then falling back to some other product they don't own yet.

    These Offer Funnels should be set up in your email marketing app, and triggered whenever either someone buys or they self-segment themselves.

    They'll run through a bunch of if/else conditions, and ultimately set a custom field (call it "bf_offer") that stores their recommended product. You'll then personalize content in your emails depending on what's stored in this field.

    Here's a quick example of what this might look like in ConvertKit:

    Want to see this automation in HD, or (if you use ConvertKit) import it into your account? Click here.

    I know this looks insane, so let me break down what's going on so you can replicate it in your email backend:

    1. There are two triggers, or ways of starting this automation. Either by someone buying (which adds the "Flag - Recalculate Offer" tag) or if the `bf_segment` field, which is what we're using to store survey responses, is updated.
    2. Next, we set `bf_offer` to blank. We don't want any existing `bf_offer` values to stick around, which might mess up the flow.
    3. Then we go through the 4 different options to GMB's survey, each of which maps to a specific program. We first check to see "did they answer 'I want more flexibility?'" (which means checking to see if `bf_segment` equals `flexibility`), then we check whether they've bought the related product yet. If they have answered flexibility and have not bought the Flexibility program, we set `bf_offer` to be the flexibility program.
    4. Not everyone will have a `bf_offer` set. If they self-segmented and already own the related product, `bf_offer` is blank. At the bottom of this automation, I'm just going through the list and asking "do they own this? No? OK, let's promote this. Yes? Alright, let's check the next product..." – starting from what I assume is the most popular program GMB offers (Elements) and working my way down.

    Even with the explanations, I realize that this might seem pretty overwhelming. This does skew intermediate to advanced, but it definitely does result in a ton of additional sales – which, no matter your email marketing experience, is a good thing!

    You're going to want to make sure everyone – even those who haven't segmented themselves – go through your Offer Funnel, probably with a bulk operation you run on your entire list. And, ideally, it should re-run whenever someone buys. This way, if your first email promotes Product A and they buy Product A, you're now promoting Product B in the next email they get from you.

    Step #3: Personalize your build-up and sales emails

    I'm not going to spend too much time now really digging into how many emails to send, when to send them, theories around how much to discount, whether or not to include bonuses, etc... we'll likely create more content around that later and publish here on the RightMessage blog, but that's a bit out of scope of this article.

    For now, I just want to help you figure out how exactly to personalize your promotional emails.

    Two things are true of the subscribers who are end up receiving your sales emails:

    1. You definitely have a recommended product attached to their subscriber record (thanks, Offer Funnel!)
    2. You most likely have them self-segmented per your "what's your goal next year?" response.

    Here's how you're going to want to use this data:

    Increase the relevance of how you introduce your promotion

    In the build-up to your promotion, along with in the introductory copy that precedes any "Buy Now" or "Learn More" links, you're going to want to align what you've got going on with their needs.

    So, for example, let's say that someone self-segmented as "I want to lose weight". It would probably make sense to have a few warm-up emails around all-things weight loss. Then, imagine this hypothetical subscriber getting an email the morning of Black Friday that reads:

    SUBJECT: Shed the pounds for good in 2020 [Black Friday deals inside]

    Hey NAME,
    I know that you said that you're looking to lose weight next year, and here at GMB we've got your back. Below you'll find a few of our programs...

    The idea here is to frame your offers against the need someone has. This is something we bring up a lot: Personalization is positioning. Personalization is relevance. Personalization is curating your messaging.

    By using your email marketing app's built-in templating, you can easily toggle in and out entire paragraphs of copy. Here's how you would do it using Liquid templating (which is what ConvertKit, Drip, and a few other products support):

    Highlight your recommended product

    With your Offer Funnel, you're going to end up assigning a specific "you should buy this" product to every person on your email list.

    This means that someone who hasn't bought anything from you and hasn't self-segmented has a recommended product (whatever the "default" fallback is that you set up in your Offer Funnel.)

    And non-customers who have been segmented have a recommended product inline with their goals.

    Customers, segmented or not, also have a recommended product that's not something they've already bought.

    What's important isn't that you necessarily recommend the perfect product. It's not about having A.I. or machine learning backing your recommended product.

    It's all about giving someone a specific product that they should buy.

    People want to be told, "Oh! You're new here? This is something that is a great entry-level product. It happens to be on sale today."


    "Hey again! So you told me that this is the big problem you're facing right now. This product will help you exactly with that. And it's on sale today."

    You should also have a dedicated email that focuses on your recommended product, especially if your promotion spans more than a single day.

    Redescribe your products

    The last thing I want to cover is how, when describing both your recommended product and all the different products you're putting on sale, is that your product descriptions don't need to be static.

    Here's what I mean by this, and this goes to the heart of how the RightMessage team and I see personalization as positioning.

    Imagine you have a product. To get specific, it's the course I just released – Mastering ConvertKit.

    If I had to describe this course with zero context around who I'm speaking with, I'd say it's a collection of video lessons that teach people how to set up a really sophisticated email marketing and automation system within ConvertKit.

    But do you remember the example I gave above?

    Let's revisit the survey question that I opened this article with:

    "2020 is just a few weeks away. How can I help you become a better email marketer next year? (choose one)"

    • I want to offer email marketing and automation services to my clients
    • I'm looking for a solid understanding of where to start with setting up automation
    • I'd like to work less by systematizing how I'm currently nurturing and selling to my audience
    • I want to improve cash flow by automating my pitch emails

    How could the answers to these questions affect the way I describe Mastering ConvertKit?

    Let's brainstorm for a second...

    The first answer is answered by consultants who want to implement this stuff for their clients, and not necessarily their own businesses.

    I might describe the course to them as:

    "Mastering ConvertKit will help you understand both strategically and technically how to create super valuable marketing systems for your clients. Even if you haven't traditionally identified as a marketer, you'll learn how to offer a new, high-value service to your clients.

    How about for the second option?

    Well, someone who answered that is most likely still a beginner. They want to make sure they're doing things right before they jump in head-first.

    "Mastering ConvertKit helps you understand how to do email marketing right – before you end up with a messy backend where you're accidentally sending the wrong stuff to your subscribers. Beginner-friendly and easy to digest, this course will leave you with a robust, flexible, and maintainable email marketing database."

    The third? This would be for someone who wants to really feel like they have a complete system in place, where they're not stuck "on the email hamster wheel" and able to spend more time focused on building new products, serving their customers, and not knee-deep in their email app.

    "Mastering ConvertKit gives you the framework to build the automated system that you've been wanting for your business. No more feeling guilty about not emailing your list weekly. No need to be stuck 'on the email content hamster wheel'. You'll learn how to nurture your subscribers and pitch them on exactly what they need at scale and entirely on autopilot."

    How about that last option? A lot of people who sell digital products are pretty tired of the peak-and-valleys that accompany the traditional way of selling online. They're sending out tons of emails that are designed to nurture their list, and – once they feel like they've built up enough goodwill – every few months they'll launch (or re-launch) a product.

    "Mastering ConvertKit helps you put your pitching on autopilot. Rather than selling to your audience during a live launch, you'll learn how to use personalized content to give your subscribers exactly what they need, behavioral segmentation to determine exactly when they should be pitched on your products and services, and more to streamline your income and give your readers a significantly better experience."

    Everyone's being offered the same exact product, but we're describing it differently depending on the needs of the recipient.

    Is it worth it?

    In the above example, I ended up writing four different ways of describing a single product.

    If I had five or ten products, I'd be looking at a lot of additional copywriting, let alone the work that needs to go into collecting this segmentation data and personalizing how I introduce the promotion.

    Smart Passive Income used this exact strategy to personalize how they pitched during their SPI-ber Monday sale in 2018.

    We worked with them to get RightMessage and ConvertKit set up to tailor the various programs they had on offer based on who their customers were (they weren't collecting "what's your goal next year?", but they were capturing information like business size, whether someone already had a podcast or email list, and so on.)

    Materially, Smart Passive Income netted an additional $104k, when extrapolated against the control, unpersonalized version. Here's their writeup.

    But it shouldn't really require A/B testing to conclude whether adding a large dose of personal relevance among the mass of "buy, buy, buy!" emails sent alongside yours would make an effect on your business.

    The real question is: would the work be worth the payoff?

    While Pat Flynn & Smart Passive Income increased sales by 2.38x (or 138%), we've found that – on average – by making your emails more relevant and, like Justin Brook said in his Facebook post, "help them [your subscribers] pick from all the options in their face", you should be able to increase sales by at least 10%.

    (I'd honestly treat a lift of just 10% as a failure, but I digress...)

    You likely have projections around what you're aiming for with your upcoming promotion, right?

    If it's $50,000, would it be worth another $5,000 to write a few more bits of copy?

    Only you can answer that question, but hopefully this guide has given you some ideas to chew over between now and the next time you plan on running a big promotion to your email list.