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Eminent Email Pros On How To Ace Email Marketing This

Generative AI permutes and combines, instead of transcending, data, leading to prosaic, superficial outputs, though unique. Should email marketers rely exclusively on AI to create subject lines this Holiday season?

Personally, I don’t think marketers should ever exclusively rely on one thing unless you have tested it so much that it has proven its full value, and nothing can beat it. I realize that AI is the new shiny object, and it can do some amazing things, but marketers should always test any tool for their specific business needs and goals.

Over-segmentation tends to complicate campaigns. How can email marketers be sober about personalizing emails, especially in the Holiday Season?

If you have been utilizing segmentation effectively throughout the year, I wouldn’t recommend changing your strategy. Too often marketers think they must do something big and bold during the holiday season because of the fierce competition to capture the customers’ dollars, but isn’t that true throughout the entire year as well?

Not all automation platforms offer seamless martech stack integration. So, email marketers still struggle with siloed data, limited API usage, limited design options, etc. How can they tackle this challenge and really milk automation this Holiday Season?

Again, I think automation is something that you should be utilizing all year long, not just during the holiday season. Automation is a great way to keep your customers engaged, reduce manual work, and allow you to focus on the bigger opportunities. Make sure you analyze your customers’ lifecycle to see where you can build automated journeys and then utilize and test those for optimal engagement.

Email clients do not need to adhere to universal standards while parsing HTML emails. What would you suggest designers do this Holiday Season to skirt the idiosyncrasies of various clients and still deliver well-designed emails?

If you are focused on send quality offers within well designed emails, you should continue to do this. As Merkle has mentioned in their 2023 Holiday playbook, it is important to appeal to the customers emotions, not just their logic through design and messaging. Instead of communicating just a discount or a convenience, demonstrate what that translates to for the shopper, whether that’s extra time with family, the opportunity to unwind with a favorite holiday movie, or more money to spend on dining out. Similarly, for experience retailers, the value-add isn’t just about the personal shopper – it’s about feelings of warmth, connection, and relaxation. Making an emotional appeal is just as important as a logical one (if not more so

How would you advise our readers on the perennial problem of deliverability during the Holiday Season? Do you think we can leverage AI to deal with this elephant in the room?

One thing marketers should realize is that if you are sending campaigns to people that want to hear from you and with offers that are of interest to them, you shouldn’t have deliverability problems. If AI can help a marketer identify and design a relevant campaign, I am all for it. The key principle is to put the customer at the heart of your plan - focus on sending personalized, relevant offers to those identified interested customers.

Generative AI permutes and combines, instead of transcending, data, leading to prosaic, superficial outputs, though unique. Should email marketers rely exclusively on AI to create subject lines this Holiday season?

I don’t recommend that any marketer rely exclusively on AI tools to write subject lines because capturing brand voice is so, so important. Even when you train these tools to your brand, they don’t get it 100% of the time, or even 60%.. But I certainly recommend using tools like Bard or ChatGPT to get the creative juices flowing and help you think of novel tactics and approaches (“Give me 10 variations of this email subject line.”) Plus: these tools make it easier to generate many versions of a subject line for testing purposes. And that is a requirement!

Over-segmentation tends to complicate campaigns. How can email marketers be sober about personalizing emails, especially in the Holiday Season?

Marketers and creatives understand the reality of personalization all too well–and they know that sending 100 versions of an email is not the path to snuggling with an eggnog by the fire this holiday season. Using a robust tool for email creation allows you to quickly create creative versions for segmentation–but smart dynamic content is the only way to personalize at scale. Creating just a few reusable modules that build on your customer data can do the trick. Also, the high-stakes holiday season is the time to invest in tools for personalization at scale, like Movable Ink.

Not all automation platforms offer seamless martech stack integration. So, email marketers still struggle with siloed data, limited API usage, limited design options, etc. How can they tackle this challenge and really milk automation this Holiday Season?

We’ve never had more robust tools at our fingertips for activating data (without being a person who knows a thing about SQL). Unfortunately, if you aren’t using the right tool now, you likely won’t be making any changes by the holiday season, so it’s time to buckle in and think about a tech stack and utilize third party tools to fill in the gaps, as needed.

Email clients do not need to adhere to universal standards while parsing HTML emails. What would you suggest designers do this Holiday Season to skirt the idiosyncrasies of various clients and still deliver well-designed emails?

The gold standard for creating consistently optimized HTML is to start with a thoroughly vetted design system and some code snippets. There are many tools on the market that have drag and drop functionality that can help you build out your repertoire faster and more efficiently (we love Parcel). Never start from scratch!

How would you advise our readers on the perennial problem of deliverability during the Holiday Season? Do you think we can leverage AI to deal with this elephant in the room?

If you plan to dig deeper into your list for holiday email sends, start your re-engagement efforts early and with a strategic eye. We always recommend avoiding big spikes in volume, which requires senders to be extra planful. Use a great deliverability monitoring tool like Inbox Monster and check your performance often!

One smaller way we’ve been using AI is through our image diagnostic tool. We suspect that ISPs are using image recognition to some degree to flag offensive content that could land senders in the spam folder–we have integrated a similar tool into our rendering engine so that brands can see how image-based content might impact reputation or deliverability. It’s only one small aspect of the equation, but every signal matters–especially during the holidays.

Generative AI permutes and combines, instead of transcending, data, leading to prosaic, superficial outputs, though unique. Should email marketers rely exclusively on AI to create subject lines this Holiday season?

AI is there to help not replace what we all do. Use it to brainstorm on new ideas for a subject line or to get alternatives to what you have already created. So ask ChatGPT to “rewrite this subject line and make it more urgent or turn it into a question or make it suspenseful”. It is important to also give AI specific instructions so the output is really useful…especially when it comes to subject lines. So tell ChatGPT to “limit the subject line to less than 50 characters, or give me 15 versions of this subject line in various emotional tones”

Over-segmentation tends to complicate campaigns. How can email marketers be sober about personalizing emails, especially in the Holiday Season?

Personalizing emails is so much more than just FIRST NAME or BASED ON PREVIOUS PURCHASE. Personalization that does really well is to focus on interests. For example, a subject line that says “For Gardeners Only…” or “For DIYers”…things that speak to the interest of the person generate huge lifts in engagement.

Not all automation platforms offer seamless martech stack integration. So, email marketers still struggle with siloed data, limited API usage, limited design options, etc. How can they tackle this challenge and really milk automation this Holiday Season?

It is important to focus on things all platforms have that have a huge impact on engagement. The ‘Friendly From. Pre-Header, Subject Line, Headline, and Call-To-Action buttons can be game changers for performance. All platforms allow for adjustments to these elements. So when you can’t do fancy integrations or cool new tests you can go back to the basics and focus on the elements that matter most anyway.

Email clients do not need to adhere to universal standards while parsing HTML emails. What would you suggest designers do this Holiday Season to skirt the idiosyncrasies of various clients and still deliver well-designed emails?

Simple is better. Get rid of navigation bars in emails and focus on the hero image of the offer you are focused on. Each email should have a goal. Whatever the goal of the email you should boil down the creative and copy to focus on that specific thing. This will allow for optimal rendering and performance.

How would you advise our readers on the perennial problem of deliverability during the Holiday Season? Do you think we can leverage AI to deal with this elephant in the room?

I actually would not focus on deliverability during the holiday season. This is the time of year that you will likely be sending to your entire database. You should expect higher unsubscribes, more bounces, and more complaints. You will be emailing people that are not your most engaged, perhaps have not opened an email since last holiday season, and likely have forgotten they are on your list. Manage internal expectations on all of this because that is normal for the holiday season and email marketing.

Generative AI permutes and combines, instead of transcending, data, leading to prosaic, superficial outputs, though unique. Should email marketers rely exclusively on AI to create subject lines this Holiday season?

It is important to note that there are a lot of great new generative AI tools out there that are helping marketers... or anyone. Tools like ChatGPT and similar can help in providing some inspiration, but they are rather limited in their suggestions which may be not performance-based or on-brand. This is true for any season, not just the holiday season.

There are professional AI-based systems that provide useful services specifically for marketers. They use data-driven predictions, “test and learn” methodology and insights. They may be even incorporated into the marketers’ existing systems, making their operations easier. These systems can also learn the voice of the brand, which is essential to stay consistent with the marketing efforts.

Also, we should not just think about subject lines anymore but all content within the email, and even cross-channel. The consumer experience doesn’t stop at the inbox, marketers can best take advantage of these tools to generate a seamless experience for content.

But beware, before any marketer goes running to invest in such a system, it is important to consider the pros and cons, and the basic prerequisites. Does the brand have enough data? The right audience size? The right amount of campaigns sent? Just to name a few essentials to feed these machines for successful results.

If the answer is “no” to many of these prerequisite questions, it may be a good idea to stick to OpenAI and similar solutions for getting some inspiration for now.

Over-segmentation tends to complicate campaigns. How can email marketers be sober about personalizing emails, especially in the Holiday Season?

Personalization can be prepared in your existing campaigns before the holiday season kicks in. If you don’t have the basics in place, it is time that you review your options now. You can aim for evergreen usage and benefits in the holiday season. Your absolute musts include information that you know about your audience i.e. name, demographics, past purchase and browse history, or their preferences.

While you are trying to be as relevant as possible, keep it simple and think about the segments that would be the most relevant during the holiday season in your business. I’m thinking beyond your top categories or gender-based segmentation.

If you are a retailer, for example, you may create segments based on the purchase power of your audience i.e. top spenders or loyalists, your “average customer” and your bargain hunters. Have different offers and content for these categories across the season.

Another great way to segment your audience is building their profile before and across the season. You can do this by simply asking what they want to hear, or via gamification and interactive content that captures your subscribers’ attention. Make sure to add these learnings to your CRM and enrich their profile for more up-to-date information for future communications.

Not all automation platforms offer seamless martech stack integration. So, email marketers still struggle with siloed data, limited API usage, limited design options, etc. How can they tackle this challenge and really milk automation this Holiday Season?

If you are struggling with the lack of data or integrations you need to make it work with what you have. There are some basics that you should have in place already, and if you do, it is your chance now to:

• Check if everything is working correctly,
• Optimize for the holiday season,
• Keep the improvements for the next year.

Let’s go through 3 automations with some quick wins for the holiday season:

Cart abandonment:

• You don’t want to leave any opportunities on the table, and this program helps you recover any shopping carts. Go ahead and check that it’s working as you have set it up already, check the creative, and the messaging, and repair any errors.
• Optimize your send time to 30-60 minutes after the cart is abandoned. If you have the option, set up a test that will help inform and optimize the best timeframe for the first cart abandonment email to be sent.
• Are you sending more than 1 cart abandonment email? Good. Make sure that you send in total 3 including the 2 reminders within 48 hours to maximise your conversion.
• During the holiday season, many retailers usually do free shipping and returns, and introduce cut-off dates to order gifts on time before a major celebration day (Christmas, 3 Kings, Sinterklaas, etc.), gift inspirations, or special offers. Does your cart abandonment include these messages that would help your audience to convert? It is time to update them for the season, just make sure to remove these after they are no longer relevant.

Welcome journey:

• Your largest amount of subscribers should come via the highest traffic season, so most probably the holiday season. So if you haven’t tested your optin process, again, you should do this now to prepare. Go ahead and fill in your lead generation forms, click on the tickboxes in your checkout, check the privacy policy links and the copy. Is everything working correctly? Are you receiving the welcome email with all the content and links as you should?
• With higher traffic volume to your website, you can test your email subscription offers and messaging and get faster results.
• Don’t forget to nurture your new subscribers, and make sure you have a full onboarding series set up. This can help deepen the relationship with your audience, as well as gather more information about them, either via link tracking or by simply asking them what they are interested in via progressive profiling.
• If possible, tag your holiday audience via what campaign they came from, as they might be cyclical buyers and not here for the usual launches or collections you are offering.

Wishlist

• If you are a retailer and have a wishlist available on your website, you can use its functionality to its fullest. Before the holiday season, you can set up your Black Month (aka November) or Gifting collections with “coming soon” messaging. Then email your relevant audience with these inspirations and encourage them to save the products they are interested in on their wishlist.
• The seasonal product interests saved in your CRM can then inform inventory management and your outbound communications. This information can help personalize your messaging to your audience in your email marketing campaigns, as well as automations where you have dynamic product recommendations in place.
• You can set up multiple automations, i.e.: When the products are
  1. available
  2. low on stock
  3. back in stock
• Email marketing campaigns can include dynamic content with personalized recommendations based on these product interests.
• While you test these tactics, you can develop a similar strategy for the future, beyond the holiday season.

Email clients do not need to adhere to universal standards while parsing HTML emails. What would you suggest designers do this Holiday Season to skirt the idiosyncrasies of various clients and still deliver well-designed emails?

People spend around 12 seconds on a marketing email, and during the holiday season, their attention is even less available. Therefore simplified email designs that are easy to skim through might take more advantage: images should be self-explanatory and impactful to speak a thousand words. On the other hand, email body copy should be optimized, and easy to read, if you are sending newsletter content (i.e. B2B), use headlines, bullet points, and highlights smartly.

Within the holiday season, there are a few email marketing campaigns that you might want to consider giving a similar look and feel following an overarching concept. These may include:

• Gifting emails
• Black Month (i.e. November)
• Informational emails or blocks i.e. free shipping and returns, gifting cutoff dates, buy now pay later messaging

Giving these specific emails an overarching concept would make them part of a series, easier to follow and recognize, even within your overall email program.

Like any season, the holiday season should always include tests, i.e. content and design tests, and the presumably higher holiday volumes can give a larger opportunity to get significant results and learnings. Just make sure you are testing against a hypothesis and monitoring predefined KPIs that will inform your takeaways.

How would you advise our readers on the perennial problem of deliverability during the Holiday Season? Do you think we can leverage AI to deal with this elephant in the room?

“Let’s send that Black Friday email to everyone in our database,” said many supervisors of email marketers in the history of emailing.

While I understand that the offers during the holiday season may be attractive to everyone on your list, one of the biggest mistakes many brands make is suddenly opening up the audience of their email campaigns and sending them to dormant subscribers who haven’t received anything for a long time. Do not do this without a comprehensive strategy.

More and more inbox providers are taking severe steps to eliminate unused email accounts after 2 years. As a result, your emailable database should have a 2-year expiry date on it, so anyone who has not engaged or purchased since then, should be avoided. Follow database cleansing best practices at all times.

You can definitely use these offers to reengage your old audience, but make sure you do this smart by gradually sending them to lesser-engaged subscribers. It is highly recommended to work together with your email service provider or a freelance deliverability consultant who guides you through the landscape of deliverability pitfalls during this complex season.

Generative AI permutes and combines, instead of transcending, data, leading to prosaic, superficial outputs, though unique. Should email marketers rely exclusively on AI to create subject lines this Holiday season?

Navigating the sea of email marketing this holiday season requires more than just a paddle; it requires a compass. AI is that compass, guiding us through a storm of ideas to find our true north. Tools like Phrasee and Persado are invaluable; they help us refine our brainstormed ideas, suggest new directions, and predict the performance of our subject lines.

But let's not forget, the compass is useless without a skilled navigator. Our creativity, intuition, and deep understanding of our audience are what steer the ship. AI is a supplement to our skills, not a replacement. It's a dance between human and machine, each playing to their strengths. We brainstorm, AI optimizes. We bring the understanding, AI brings the data-driven insights. Together, we test, analyze, and optimize until we craft a subject line that not only grabs attention but captures hearts. And then, we monitor and adapt, always ready to change course if needed. Because in the vast ocean of email marketing, it's the messages that truly resonate that reach their destination.

Over-segmentation tends to complicate campaigns. How can email marketers be sober about personalizing emails, especially in the Holiday Season?

Segmentation isn't just a checkbox in your email marketing strategy; it's the linchpin, especially during the holiday season. Segmenting your email list ensures that your messages hit the mark, both in relevance and timeliness, for each recipient.

Consider these factors when segmenting your list this holiday season:

• Past purchase behavior: Cluster customers based on their previous purchases to target them with products and promotions that pique their interest.
• Engagement level: Group customers by their engagement intensity with your brand, and focus on those most likely to be receptive to your messages.
• Location: Segment customers geographically. This facilitates sending targeted messages to customers in specific locales.

Several email marketing tools, such as Mailchimp and Braze, can automate the segmentation process and simplify managing extensive email lists.

Investing time in segmenting your email list this holiday season can elevate open, click-through, and conversion rates, ultimately amplifying sales and your bottom line.

Not all automation platforms offer seamless martech stack integration. So, email marketers still struggle with siloed data, limited API usage, limited design options, etc. How can they tackle this challenge and really milk automation this Holiday Season?

The holiday season is a maze of siloed data, limited API usage, and design constraints. Yet, it's the golden hour for automation. Begin by selecting an automation platform that aligns with your martech stack, such as Mailchimp or Klaviyo. Harness APIs for data flexibility and control. Utilize design tools to craft personalized, captivating emails, elevating open rates, click-through rates, and conversions. Schedule targeted messages at prime times and monitor results for ongoing refinement.

For those wrestling with platforms lacking these capabilities, Zapier is a knight in shining armor. It connects disparate apps and tools, automating data exchange and workflows, dismantling data silos, maximizing API and design potential, and minimizing time and errors.

By combining the power of these platforms and tools, you can overcome challenges and maximize automation efforts this holiday season.

Email clients do not need to adhere to universal standards while parsing HTML emails. What would you suggest designers do this Holiday Season to skirt the idiosyncrasies of various clients and still deliver well-designed emails?

Crafting emails is an art and a science, a dance between aesthetics and functionality. The essentials? A single-column layout, a compelling call-to-action, alt text for images. Tools like Litmus or Email on Acid can help us test across clients, but the human eye is the ultimate judge. Our mission? To create emails that don't just work, but enchant.

To navigate the quirks of various email clients and deliver well-designed emails this holiday season, consider these tips:

• Embrace responsive design.
• Have a plain text fallback.
• Use universally supported HTML elements.
• Test on multiple devices and clients.
• Utilize a preview tool.

Additionally, incorporate high-quality images, clear and concise language, a strong call-to-action, and track your results for future improvement.

By following these guidelines, we can ensure our holiday emails are not only well-designed but also reach the widest possible audience. Let's create emails that resonate, engage, and inspire action.

How would you advise our readers on the perennial problem of deliverability during the Holiday Season? Do you think we can leverage AI to deal with this elephant in the room?

Deliverability is a perennial challenge, especially during the holiday season when inboxes are flooded. AI can certainly help in many ways, from optimizing subject lines to managing your email list and analyzing deliverability trends. It can help identify and filter spam, personalize emails, and optimize content for deliverability.

However, it's not a silver bullet. There are aspects that require a human touch, like building relationships, understanding context and cultural nuances, and managing crises. It's also crucial to maintain ethical practices, adapt to new trends, and handle exceptions that AI is not programmed to address.

This holiday season, use AI as a tool to enhance our email marketing efforts, but let's not forget the importance of the human touch in crafting messages that resonate, building relationships, and navigating the nuances of communication. It's the combination of AI and human intelligence that will truly help us tackle the elephant in the room.

Generative AI permutes and combines, instead of transcending, data, leading to prosaic, superficial outputs, though unique. Should email marketers rely exclusively on AI to create subject lines this Holiday season?

Undoubtedly AI is playing a bigger and bigger part in our work. Many of the platforms now incorporate AI into their editors. But AI isn’t foolproof. There absolutely has to still be input from the email marketer whose creativity and understanding of brand voice will play to the emotions of the audience that is not understood by data alone. Relying on AI alone could lead to cultural faux pas where it doesn’t yet understand the impact of current news and current affairs.

Over-segmentation tends to complicate campaigns. How can email marketers be sober about personalizing emails, especially in the Holiday Season?

With the volume of emails increasing significantly during the holiday season, it’s vital we consider if we are sending the right message at the right time to the right person so they don’t get email fatigue. Remember also that they could also be gift buying for other people and not just themselves, so keep a closer eye on browsing history and purchasing behaviour. Planning your campaigns with roadmaps well in advance will help here.

Not all automation platforms offer seamless martech stack integration. So, email marketers still struggle with siloed data, limited API usage, limited design options, etc. How can they tackle this challenge and really milk automation this Holiday Season?

The holiday season and indeed the whole of Q4 is not the time to be experimenting with new martech. Go with what you know works and monitor for any large scale issues. Post holidays, reflect on your experiences and only then test and trial new automations.

Email clients do not need to adhere to universal standards while parsing HTML emails. What would you suggest designers do this Holiday Season to skirt the idiosyncrasies of various clients and still deliver well-designed emails?

We’ll never get perfect design that renders across all email clients (we wish). We have to ensure that emails are still readable and engaging by employing alt text on all images so readers still understand the message, minimising the amount of images and attempting to keep emails as light on code as possible. Again, now is not the time to be trying out a new style of design and hopefully you will have done much testing earlier in the year, including using testing software like Emails on Acid and Litmus to preview how your emails looks before they are sent.

How would you advise our readers on the perennial problem of deliverability during the Holiday Season? Do you think we can leverage AI to deal with this elephant in the room?

To optimise deliverability during the holiday season, make sure you’re sending to clean your lists. Use Zero Bounce or Mailercheck to clean up old email addresses that are no longer used or have been taken over by spam traps. And now is not the time to be sending to those who are non-engagers. Whilst sending volume will go up, don’t suddenly go from one email a week to daily emails and try to remain consistent in terms of content, from name, imagery and tone.

Generative AI permutes and combines, instead of transcending, data, leading to prosaic, superficial outputs, though unique. Should email marketers rely exclusively on AI to create subject lines this Holiday season?

Exclusively, absolutely not. While generative AI is impressive at a few things, it only sometimes knows or even understands the audience you are sending to and can consequently get it wrong. In addition, AI needs to learn something historical on subject line performance or testing you have done. Yes, generative AI can be wrong, and don’t let anyone tell you differently. I would advise that at least an A/B test (preferably an A/B/C/D test) with an AI-generated subject line or lines against those you write to gauge results be performed. Use a solid KPI beyond opens to determine if AI subject lines can constantly outperform over an extended period of time. Ensure that the subject lines you test against have distinct differentiators, such as tone or urgency, and for goodness' sake, write a plan with a hypothesis and results to keep track of which ones performed the best.

The bottom line is to prove it and only put some of your email revenue into one AI basket.

Over-segmentation tends to complicate campaigns. How can email marketers be sober about personalizing emails, especially in the Holiday Season?

Personalization in email is different for everyone: the marketer, the subscriber, and the customer. Email marketers must be careful because it does not live in a vacuum. Hyperpersonalize to those whom you have a lot of zero-party data on, who are past customers, highly engaged, or who show a high propensity to purchase in other channels. Marketers should consider less or even no personalization to those not falling into any of the segments above.

The last thing your organization wants to do is creep someone out with “personalization” without really knowing them or appending data. Don’t cross the “creepy” line.

Instead, focus on what data you have to create a personalized experience in email and test into very focused segments on whether or not personalized emails actually work. Guess what, it might not. As much as we hear people wanting the brands to “know” them and personalize their communications, your customers or subscribers might not know how far brands can go. Lastly, weigh the level of effort it takes internally to pull off personalization in each email, as it might reflect a positive ROI.

Not all automation platforms offer seamless martech stack integration. So, email marketers still struggle with siloed data, limited API usage, limited design options, etc. How can they tackle this challenge and really milk automation this Holiday Season?

Email marketers have a lot to do, and planning for Holiday should have started in Q2, especially regarding automations for this coming year. The goal is to prioritize the level of effort in using automations to make iterative improvements in the email program. It’s sort of like drawing up a testing plan, and things to weigh when it comes to implementing automation are:

• A hypothesis on what you are trying to achieve
• Details of the automation and the business value it will provide both internally and externally
• Levels of effort - (e.g., design, tech implementation, integrations, etc.)
• Level of impact on the organization

If there has been no advanced planning, I would recommend starting with one or two automations that you can put in place with the lowest level of effort coupled with the highest level of impact. There is no magic bullet for any organization; it truly depends on what you have now vs. where you want to go and achieve. Start small if you can, and don’t overwhelm others on the teams to get it all done. If you can’t implement any new automations, consider optimizing your current ones.

Email clients do not need to adhere to universal standards while parsing HTML emails. What would you suggest designers do this Holiday Season to skirt the idiosyncrasies of various clients and still deliver well-designed emails?

It’s hard to please everyone, especially in email client-land, and I can sympathize with designers who try to be everything to anyone. In fact, if your organization tests emails internally to people who use Outlook, but <1% of your audience uses Outlook, you have to ask, what’s the point, and why am I doing this?

You only need to determine the 5-7 biggest email clients your subscribers are on to design and refine the templates you plan to send over holiday. When some SVP of something or other C-Suite person asks why their email looks the way it does in “their” outlook, ask them the following question:

Am I designing emails for you or for our clients? (Then hand them a report of the top 5-7 clients and reference how big that audience is in comparison to the entire subscriber base.)

Don’t focus on designing for everything and everyone, as it might not be worth your time. Having the data to prove that what you do is the right thing and design for conversion, not beauty. Sometimes, ugly wins.

How would you advise our readers on the perennial problem of deliverability during the Holiday Season? Do you think we can leverage AI to deal with this elephant in the room?

Sorry to burst your bubbles, but AI can’t fix or prepare you for deliverability issues during the holiday season. Deliverability is 98.7% on you, the marketer, and your practices leading up to and during the holiday season. It’s rarely your ESP's fault or something else other than you that made deliverability a challenge.

Pulling a list of 9-month inactives who haven’t been mailed this year, with the hope and prayer that they will respond, will result in consequences AI cannot solve. Deliverability is consistently HARD work and something that either you need to monitor and mitigate or hire someone who can always do so. AI will not pull your organization out of the depths of blocklists, deferrals, or junk folders because dealing with these things can sometimes be a manual process.

Generative AI permutes and combines, instead of transcending, data, leading to prosaic, superficial outputs, though unique. Should email marketers rely exclusively on AI to create subject lines this Holiday season?

Here’s the thing: I really wanna like AI. And I do, for certain things. It tosses out ideas when everything you write is…meh. It can dive deep into your email stats, guiding you towards subject lines that rake in the highest opens and clicks while simultaneously helping you steer clear of the ones triggering high unsubscribes and spam complaints.

My favorite part? When it’s plugged into your other first-party data like website traffic, conversions, and revenue, identifying what's bringing in the big bucks and building more alternatives around it becomes so easy, it feels like you just found multiple gifts hiding under the backside of the Christmas tree.

But here’s my beef: it all sounds the same! Just today, three different ecomm brands sent me the same exact email. Different sender, company name, and branding, but the subject line and the full body of the message were exactly the same. Imagine how fatigued readers will be after seeing the same subject lines and preview text they once found enticing used over, and over, and over again. Talk about diminishing returns.

So you’ve gotta mix it up…the way humans do! With our wit and wisdom and the kind of total randomness and novelty you can only expect from a bot when your prompts are out of whack.

My suggestion is to use AI for subject line inspiration, not exclusive implementation. It’s ok to let it guide you down the data-driven path that might be right for your brand, as long as you don’t follow it off the end of a cliff! Keep your oh-so-human thinking cap on to ensure your brand’s voice remains unique.

Over-segmentation tends to complicate campaigns. How can email marketers be sober about personalizing emails, especially in the Holiday Season?

Personalization boosts engagement and conversions, but it can drive your email recipients away if you get it wrong. And the more granular the segmentation, the more room for mistakes. The end result? Wonky personalization that screams, "we really don't get you." Not many things are more painful as a marketer than by being laser-focused...on entirely the wrong details.

Figure out the right balance for your company by diving into your data:

• What do you know about your subscribers?
• How much confidence do you have in the accuracy of that information?
• How can you apply that intel to personalization at scale?

Once you’ve made your holiday personalization list, check it twice—maybe even thrice. Stakes are high this time of year, so either stick with what’s already been working or make incremental adjustments — and test, test, test! — to ensure the changes you’re making have been rolled out successfully and are resonating with your email audience. Otherwise, you might find yourself on Santa’s blocklists, right next to that naughty little Elf on the Shelf.

Not all automation platforms offer seamless martech stack integration. So, email marketers still struggle with siloed data, limited API usage, limited design options, etc. How can they tackle this challenge and really milk automation this Holiday Season?

Ah, the holidays: a dizzying mix of pumpkin spice, end-of-year sales rushes, and...data silos? For email marketers, the anxiety is all too real, especially when racing against the clock. But don’t let data challenges and lackluster automations get your tinsel in a twist—there are lots of ways you can enhance what's already in place. Here are a few:

Refresh existing templates. Nobody’s got time for an overhaul right now and you can forget about creating emails from scratch, but tweaking your color schemes and adding festively branded elements on your best-performing layouts can go a long way to making old templates feel fresh and relevant. Add a thoughtfully placed emoji in the subject line or holiday pun in the preview text and you might just have a record-breaking automation on your hands.

Manipulate the data manually. Ugh, I know. Manual data manipulation. Gross. But if you’re willing to roll up your sleeves, exporting vital segments or data points and manually integrating them can be a worthy workaround, helping ensure your messages resonate with subscribers. It’s a hands-on solution removing the need for short-term solutions like Zapier to bridge your data gaps.

Embrace broad segmentation. Ditch the complexities of ultra-fine segmentation for now unless it’s already in place and working well. Tick-tock on the holiday clock, remember? By using broader segments based on purchase categories or engagement metrics (particularly during past holiday seasons), you’ll give your emails a better chance at landing in the inboxes (and hearts) of your subscribers without the need for fully integrated platforms.

Email clients do not need to adhere to universal standards while parsing HTML emails. What would you suggest designers do this Holiday Season to skirt the idiosyncrasies of various clients and still deliver well-designed emails?

Getting emails to render HTML properly across various email clients can feel a bit like sledding down a hill—thrilling, but full of unexpected bumps. And we all know Microsoft is the brother who occasionally knocks you sideways after you’ve climbed halfway back up the hill.

I'm more of a strategist than a designer. But if there's one thing I've learned, it's that combining data-driven insights with tried-and-true practices is the way to go. Here are a few ways to stay upright while ensuring your emails look their best:

Prioritize with data. Understand where the bulk of your emails are landing. Is it Gmail? Outlook? Apple Mail? By knowing which platforms the majority of your audience uses most often, you can allocate your design efforts accordingly.

Seek out similarities. Some email clients share commonalities in how they render HTML. If you find a solution that works for one, it might just solve issues in another. For example, if your design looks great in Yahoo, there's a chance it could translate well to AOL.

Know when to sidestep. Let’s be real, some email clients just don’t play nice. (seriously though, can someone call Mr. or Mrs. Microsoft to come take this kid home already??) Before you dive into intricate fixes, ask yourself if it’s worth the effort. Sometimes, the best strategy might be segmenting that audience and offering an experience better suited to their client’s quirks.

Use email testing tools. I would be remiss if I didn’t mention platforms like Litmus or Email on Acid, which show previews of how your emails will render across numerous clients and platforms…like 100+. By very quickly spotting issues in advance, you’ll have more time to spend tweaking your designs for the best possible outcome.

Stick with what works. The world of email design is filled with ever-evolving standards and practices. Most of you reading this know that better than I do. Yet, some basics remain steadfast. Lean into these well established methods, and if it ain’t broke, don’t fix it! Especially when you're short on resources.

How would you advise our readers on the perennial problem of deliverability during the Holiday Season? Do you think we can leverage AI to deal with this elephant in the room?

Truth be told, inbox providers are a little robotic themselves: unfazed by the festivities. Those anti-spam filters are machines looking for patterns of spam and fraud, after all. And crime doesn’t take a holiday.

They'll side-eye sudden spikes in volume and negative recipient reactions, regardless of whether you're attempting to send out holiday cheer or putting coal in peoples’ inboxes. If you're planning a widespread holiday email bash and all of your inactive subscribers will be invited, AI can help you execute that ramp up period in a way that maximizes reach without introducing too much risk. Just be sure to kick things off with a reactivation campaign to gradually build your volumes while you warm up disengaged subscribers.

AI can also help you watch out for problems with inbox placement—and those little robots don’t need to sleep, so put them to work! Tasks such as monitoring key metrics, sending alerts to humans when they detect an anomaly, and adjusting traffic shaping to send mail more slowly or through a different IP are just a few examples. Things can get a little whacky during the holidays, so having a second set of virtual eyes can help you get some rest (and get that holiday shopping done) without worrying your emails are missing the inbox.

One word of caution though…don’t put your email program on ‘set-and-forget’! Relying too heavily on generative AI for subject lines or body copy could unwittingly change your tone of voice or the meaning of your message, leading recipients to engage differently. All of these could impact your email engagement rates – something mailbox providers watch closely to determine what deserves inbox placement. Make sure you’ve got human and robot eyes watching your stats closely to ensure spam complaints are remaining low while your conversions (hopefully) go up.

Generative AI permutes and combines, instead of transcending, data, leading to prosaic, superficial outputs, though unique. Should email marketers rely exclusively on AI to create subject lines this Holiday season?

There is no doubt that generative AI is very exciting and unlocks new ways to approach data, that were previously simply too complex or unwieldy to do entirely with “human” work. However I think it may be counterproductive to hand over the keys completely to AI driven automation. These tools are there to help marketers do their work better, not to replace them. I would still expect that the most successful marketers will use this as a guide, not an autopilot.

Over-segmentation tends to complicate campaigns. How can email marketers be sober about personalizing emails, especially in the Holiday Season?

It is true that over-segmentation can complicate email campaigns, sometimes unnecessarily. One important thing to remember is that the holiday season is a time when a consumer’s purchasing preferences will be broader - as they seek to buy gifts for other people. Therefore we should think carefully about whether the data we have, that would usually be used to narrow scope, should instead be used to inform wider preferences. This can be as simple as including a personalised part of the email, but also including products/offers that may at first look seem irrelevant to their personal preferences. As ever, it is a good opportunity to test and review results.

Not all automation platforms offer seamless martech stack integration. So, email marketers still struggle with siloed data, limited API usage, limited design options, etc. How can they tackle this challenge and really milk automation this Holiday Season?

Many orgs do indeed have challenges getting siloed data to sync up, and as a result struggle to deliver a cohesive experience. However often there are fairly straightforward ways to at least get something moving. This is a good season to remember that done is better than perfect - getting something, anything, moving is going to start getting you results. Think about what you can control - often easy wins like fairly consistent visual and brand design will get you a long way. Often a large amount of the overall value of automation is in the staples - things like welcome sequence, abandoned cart, post purchase, some kind of basic loyalty recognition, stock notifications etc - can get a lot of progress happening.

Email clients do not need to adhere to universal standards while parsing HTML emails. What would you suggest designers do this Holiday Season to skirt the idiosyncrasies of various clients and still deliver well-designed emails?

This holiday season, marketers should embrace the idea that emails don’t have to look exactly the same in every email client - instead we should try to make the experience the best we can - even if that is different - for the email client that the recipient happens to be opening with. That means coding with enhancements for more capable email clients such as iOS, and falling back to a good experience as some support drops out in Gmail and Outlook. As ever, leading with accessibility for all is key.

How would you advise our readers on the perennial problem of deliverability during the Holiday Season? Do you think we can leverage AI to deal with this elephant in the room?

There are some interesting AI driven solutions that are starting to emerge in the deliverability space, however I’m wary of betting such an important revenue generating season on tech that is still developing. Deliverability is a year round challenge - one that is often actually caused by damaging our reputation around the holiday sales season for a cheap buck. I’d suggest that overmailing and pushing our luck in the holiday season could well be the cause of problems - we should address this by marketing in a more sensible and responsible way rather than finding tech solutions to push our luck further.

Generative AI permutes and combines, instead of transcending, data, leading to prosaic, superficial outputs, though unique. Should email marketers rely exclusively on AI to create subject lines this Holiday season?

I think because AI only ever recombines or assesses past content, it kind of can’t be relied upon exclusively! When you use AI, train it using your own brand’s data from past holiday seasons or similar sales. Let the “computer” help you learn precisely what language works at what point in a sale or season and what frequency is optimal. You can do a fair amount of that analysis without AI, too, but AI can help you get to the best version of things – or suggest a combination of best performers – faster, by processing a LOT of data quickly. This lets you stick to editing. Focus your own time on brand voice, readability and context. Let’s face it, most AI copy isn’t always perfect (yet)!

Over-segmentation tends to complicate campaigns. How can email marketers be sober about personalizing emails, especially in the Holiday Season?

Think of everything you do not just in terms of Return on Investment of money but also return on your invested time. Sure, you could make 10 versions of a campaign and spend 6-8 hours on each: creative, development, QA, setting up and cross checking each deployment… But would something else be a better return on the 60+ hours you’ll spend? Focus on creating unique versions only when the cadence or reason to buy varies for a segment. Then, use variable data to make those versions more tailored to each subscriber, like images of the subscriber’s last product purchased or mentioning their last purchase date. Variable data also allows us to customize the content (or timing) of an email at scale without spending time creating a whole custom email version.

Not all automation platforms offer seamless martech stack integration. So, email marketers still struggle with siloed data, limited API usage, limited design options, etc. How can they tackle this challenge and really milk automation this Holiday Season?

If you just need a code-free way to integrate 2 systems, check out connector marketplaces like Zapier. If you use any of the more common entry-level platforms, there’s probably a Zapp that connects it to common website forms/platforms or CRMs. The bottom-line truth is that data is required to power automation. So even if you can’t use a plug-in or Zapp, work with your interdisciplinary teams to justify creating and maintaining a sync between data sources. Remember, though, that every team has their own goals and task lists and this shouldn’t just be you “petitioning” them to make your sync happen. Write a case study where the sync powers a new automation that could lift transactions or revenue. Use an existing published case study from a similar brand, industry or product price point to show the potential impact, i.e. “When we can sync abandoned cart users to our email platform in real time, we can automate a reminder email series that typically results in a 3%+ conversion rate, potentially creating revenue up to…”

Email clients do not need to adhere to universal standards while parsing HTML emails. What would you suggest designers do this Holiday Season to skirt the idiosyncrasies of various clients and still deliver well-designed emails?

Test your emails. Test them on all of your own devices, sure, but if you can, test them through rendering platforms like Email on Acid or Litmus. The more flexible your code is, the better chance that it’ll probably look good in most places, but you won’t know that the dark mode default color swap for your “brand gold” isn’t “poop brown” unless you actually test it.

How would you advise our readers on the perennial problem of deliverability during the Holiday Season? Do you think we can leverage AI to deal with this elephant in the room?

Deliverability is the fly in email marketers’ ointment for sure, but it’s become so much more complex to track and address. Every inbox may react differently, so saying you “went to the spam folder” at Gmail isn’t really universally true. Plus, when email volume gets heavy – like at the holidays – it seems like inbox filters become more sensitive or have a few days where everyone (good/bad/ugly) is getting swept to spam folders. Again, your best bet is to use tools. If you can at least estimate your inbox placement and stay alert to issues, you can know when to slow your cadence or address a block of some kind.

Generative AI permutes and combines, instead of transcending, data, leading to prosaic, superficial outputs, though unique. Should email marketers rely exclusively on AI to create subject lines this Holiday season?

Rely on it? No. Use it for inspiration? Yes. But use it strategically. Don’t focus on short or long subject lines, focus on the humans who will be opening the email. Brief your AI tool to leverage principles of persuasion such as reciprocity, social proof, authority, loss aversion and scarcity, as well as cognitive biases such as emotional appeal, Anchor Effect, Endowment Effect and Confirmation Bias – just to name a few. These will help to motive and appeal to your audience using behavioural science.

Over-segmentation tends to complicate campaigns. How can email marketers be sober about personalizing emails, especially in the Holiday Season?

Over-segmentation also can cause reduced ROI due to the additional effort, so getting the balance right is necessary. A good tactic for the holidays is to design a send to all campaign, with personalized recommendations based on their previous purchases or browsing behaviour. This way you’re ensuring your reach is wide, but for anyone who has purchased or been to the site, there will be some covert personalization, which will help them.

Not all automation platforms offer seamless martech stack integration. So, email marketers still struggle with siloed data, limited API usage, limited design options, etc. How can they tackle this challenge and really milk automation this Holiday Season?

If you don’t have a cart abandonment or browse abandonment programme in place as yet due to tech limitations, I would encourage you to go and check out the multitude of real-time providers and get set up. Usually, the only requirement is to put some code on your website and the specialist company can advise and help you to get your first programme in place. You can always look to optimise and refine it soon after the holidays, but this way you will at least have a programme in place to ensure you’re making the most of your unknown buyers.

Email clients do not need to adhere to universal standards while parsing HTML emails. What would you suggest designers do this Holiday Season to skirt the idiosyncrasies of various clients and still deliver well-designed emails?

Ensure your emails are either responsive or designed for mobile-first (one column). The main issue this year is with Dark Mode and its rising popularity. You firstly should realise that you will never have it perfect for all email clients and devices. Secondly, identify your top two main email clients and devices and design for those two.

How would you advise our readers on the perennial problem of deliverability during the Holiday Season? Do you think we can leverage AI to deal with this elephant in the room?

If you’re ramping up your database and planning on mailing addresses that haven’t been contacted in a while, then you need to create a detailed ramping up/warming up schedule and monitor it on a daily basis. There are some fantastic AI tools that you could brief and let them do the math and calculations for you, alternatively, you can do them yourselves. Be prepared to tweak the plan as you go along so that if you see signs of any issues, you can respond quickly.