16 Experts Talk about Holiday Email Marketing

How early/when do you recommend brands start their holiday planning? And why?

I recall working at a e-commerce brandwhere we would conduct our Christmas photo shoots as early as September.

When it comes to email preparation, warming up your audience is crucial. Before the holiday season, it’s important to gradually increase the number of emails you send. These emails should be engaging and valuable to the recipient - never sent just for the sake of it. This warm-up process can take a few months, so even if your holiday emails aren’t fully prepared yet, it’s essential to start sending these engaging emails now.

For the Black Friday season, I recommend having your entire calendar planned out by September. Incorporating campaigns like ‘Back to School’ and ‘Halloween’ can be excellent additions to your warm-up strategy.

Aside from increasing frequency, what is your top recommendation for standing out in crowded inboxes during the holidays?

1. Optimize the "From" name. Change the "From" name to something seasonally relevant, like "{Brand Name} Black Friday Deals" or "{Brand Name} Holiday Offers." This immediately signals to the recipient that the email contains special, time-sensitive content.

2. Enhance subject lines with rich text. Use rich text formatting (italic, bold, strikethrough) in subject lines to make them more eye-catching. For instance, you can use tools like https://www.cloudhq.net/g_suite to format your subject lines effectively.

3. Deliver tangible value. Focus on clear, quantifiable value in your messaging. Highlight exactly how much the user can save by comparing regular prices to discounted ones, making it easy for them to see the benefit of acting now.

How early/when do you recommend brands start their holiday planning? And why?

Email marketers should begin planning for the holiday season at least six months in advance, typically starting around June or July. This early start is crucial for developing a comprehensive strategy that includes content creation, segmentation, and scheduling, ensuring everything is in place well before the holiday rush begins. And it's even more important this year where the holiday season is particularly short, with only 27 days between Thanksgiving and Christmas. This adds extra pressure on email marketers to maximize every opportunity.

The condensed timeframe means there's less room for error and less time to capture consumer attention. Marketers will need to adjust their usual strategies by launching campaigns earlier and deploying much stronger personalization. This approach helps maintain a steady presence in consumers' inboxes during the shorter holiday season.

Additionally, early planning allows email marketers to test different approaches, optimize deliverability, and refine their messaging based on customer behavior and preferences. With the shorter season, every day counts, so having a well-coordinated and flexible strategy in place is essential to driving engagement and conversions. By planning ahead, email marketers can effectively navigate the challenges of a shorter holiday season, ensuring that they make the most of this critical sales period.

Aside from increasing frequency, what is your top recommendation for standing out in crowded inboxes during the holidays?

My top recommendation for standing out in crowded inboxes during the holidays is to create highly personalized and impactful emails tailored to each customer. Achieving this at scale requires leveraging advanced technology, such as AI-powered tools and customer data, to craft 1:1 messaging. By utilizing dynamic content that adapts in real-time, you can deliver immersive experiences that not only capture attention but also drive meaningful engagement and conversions.

To drive conversions, target your audience based on expected behaviors or actions, such as likelihood to purchase or churn, customer lifetime value, and discount affinity. This allows you to craft messages that resonate on a deeper level with each recipient. Additionally, use personalized recommendations to cross-sell and upsell, tailoring these suggestions to your subscribers' behaviors, actions, and preferences.

It's about making every email feel uniquely relevant, ensuring it resonates and compels a purchase. In the peak holiday season, it's not just about standing out—your emails need to inspire action amidst a sea of competing messages. By focusing on personalization and strategic targeting, you can ensure that your emails not only get noticed but also lead to meaningful results.

How early/when do you recommend brands start their holiday planning? And why?

I recommend brands start holiday planning at least a few weeks prior to their email marketing planning cycle. For example, if the email planning cycle normally starts 12 weeks prior to an email deployment, I’d recommend starting 16 weeks prior to deployment dates.

This guidance is flexible depending on whether the brand sells high consideration products / services or low consideration products / services.

Higher consideration purchases, such as electronics, luxury items, and major appliances, typically require a longer decision-making process. Subscribers need time to research, compare options, read reviews, and consult with others before making such significant investments. For these categories, add a bit more buffer to the holiday planning process.

Early campaigns can provide detailed product information, highlight unique features, and offer customer testimonials to aid in the decision-making process.

On the other hand, lower consideration purchases, such as clothing, accessories, and everyday household items, do not need extensive deliberation. Consumers are more impulsive with these purchases, driven by the best deals and immediate needs. For these products, holiday marketing can begin closer to the actual shopping season, focusing on creating urgency through limited-time offers, flash sales, and engaging, festive promotions.

Aside from increasing frequency, what is your top recommendation for standing out in crowded inboxes during the holidays?

I'd recommend brands create a special early-access opt-in list for early access to the best deals before any other subscribers. Opt-in to the early access list can be collected via a simple web form that's advertised in the final days before the brand's best deals of the year. Brands then advertise to this list when the best deals are going to drop, creating even greater anticipation from the list. While the early-access opt-in list may represent a small percentage of your overall list (10%), I've seen these tiny lists create more sales than the 90% of subscribers who are not opting in to early access.

How early/when do you recommend brands start their holiday planning? And why?

It's never too early to plan for the holidays. Even after last years holiday, we did a review of what did and didn't work so we could start planning for the next year. Black Friday/Cyber Monday is the most competitive and most lucrative marketing holiday of the year, so the further in advance you can start planning, the more prepared you'll be. And each year we're seeing marketing campaigns earlier and earlier, so being ready Sept 1 before Halloween is so key.

Aside from increasing frequency, what is your top recommendation for standing out in crowded inboxes during the holidays?

You have to think outside of the box (or inbox) in order to stand out during BFCM. Your subscribers are getting thousands of emails a day, Some things that help:

Use emojis in your subject line and keep your preview text line clean by using some coding in your preheader to create blank space.

Send during off peak times when others aren't sending emails. Think about Sunday nights and even Monday mornings-- typically not popular email sending times. If everyone sends an email on Black Friday at 9am, send one the night before or later in the day Black Friday.

Most importantly, keep your emails super simple and easy to read so that your subscribers can skim them quickly and click that button!

Lastly, make sure this is your absolute best offer of the entire year. People are expecting great promotions, so save your very best for the holiday season!

How early/when do you recommend brands start their holiday planning? And why?

Initial campaign concepts and direction should be locked in for BFCM no later than mid September in order for the design team to provide visual identity mockups with ample time for campaign leaders to review and disseminate and prioritize with cross-channel stakeholders.

Aside from increasing frequency, what is your top recommendation for standing out in crowded inboxes during the holidays?

Make sure your email sending reputation is in good standing and that your IP can handle the increase in delivered emails. The last thing you want is for your hard work before the busiest email season to not end up in the inbox!

In addition to offering a great deal, be playful! Consumers are anticipating your emails, so make it worth their wait. While your primary KPI will be revenue-based, what is the "why" for your customer? Surprising, delighting, and engaging customers is often overlooked, but that's the real bottom line of a successful campaign and email marketing program – you don't want the relationship to become purely transactional.

How early/when do you recommend brands start their holiday planning? And why?

As soon as possible? 😁 I don’t necessarily have a specific date in mind, but I I think having conversations in early as advance is ideal. How about we say shortly after Labor Day? With that said, busy seasons, organization size, department size and more variables all play a part, but too late is worse than too early. I think if you give yourself a few months, you have enough to see what products are and aren’t in demand as you look to what’s able to be sold. You also give yourself time to work backwards and start testing certain variables that you could use in your emails during the holidays.

During the season, we’re usually able to start planning a few months in advance, but because our business is so reliant upon demand leading up to a game, there are times when we do have to play a lot of things by ear even if we THINK we have an idea of what we want to do.

A trade could happen during the middle of the season and gear we were planning to sell could essentially not be in demand and a game with less demand could all of a sudden be a gem. You never know. I also think it’s important to plan as early as possible so you can start to map out initial campaigns and follow up campaigns you want to send during that timeframe and make sure everyone is on board, especially if the campaigns involve a lot of stakeholders. While “more is more” volume wise during the holidays, planning ahead also allows you to see volume at a high level and determine what could be scaled back or consolidated due to too much messaging.

Aside from increasing frequency, what is your top recommendation for standing out in crowded inboxes during the holidays?

Because volume ticks up substantially during the holidays, I would recommend a mix of selling and telling right away in your subject lines. What’s selling? “Cyber Sunday Steals Just Got BIGGER!” versus “Start Snagging Tees As Low As $5” (telling). When you sell what’s inside the email, you force consumers to stay on their toes and naturally pique their curiosity when they have to ask any of the five W’s: who, what, where, when and why. If you tell the customer what’s inside, they don’t need to ask what’s inside - at that point they’re just deciding whether the product is what they want. There are schools of thought that may be pro-either of these methods, but I think leaning into both over the holidays keeps customers on their toes.

This is also simple and maybe plainly obvious, but testing what messaging resonates with your customers BEFORE the holidays arrive could help drive your strategy when it’s time to send.

I also think keeping your call-to-actions clear and as high above the fold as possible are musts along with getting to the point knowing customers have countless other emails to sift through. If you put yourself in the customer’s shoes, you want to know what the deal is and how long you can take advantage of said deal.

One more method I think could help brands stick out from the inbox is to ask people if they want to be on a VIP BFCM/Holiday list so they are the first to get the scoop on updates. Keep all of this in mind so you don’t get sent to the junk drawer!

How early/when do you recommend brands start their holiday planning? And why?

If by holiday planning you mean just the emails, a month in advance is more than enough. That’s the easy part.

But if we’re talking:

• Growing your (quality) list and keeping it clean
• Testing your offers, messaging, CTA, design, segmentation, etc.
• Making sure your deliverability is on point
• Developing a post-holiday retention strategy
• Engaging your audience to build affinity and loyalty for your brand

Then you need to start as early as possible. These are year-round efforts.

If the holiday season is the Super Bowl for DTC brands, you know the game isn’t just won by whatever prep you did in the past month. It’s a continuous work that you put in that makes the sum greater than its parts.

Aside from increasing frequency, what is your top recommendation for standing out in crowded inboxes during the holidays?

Try sending plain text messages, especially if you’ve always sent image-heavy emails. This is a pattern break and could help you stand out in a sea of HTML emails.

How early/when do you recommend brands start their holiday planning? And why?

You should start thinking about your holiday planning as early as last holiday period. Firstly evaluating the past, thinking about what went well, what went wrong and how can you improve from the previous holiday period, but also start building on a strategy and being prepared, as well as considering your sales targets for the upcoming year, what do you need to do to meet them. You need to consider what do you need to start testing to ensure you’re sending the best possible emails over the holiday period, what can you start optimising now, how are you going to segment your database, do you need to profile your database further I.e. do you need to implicitly profile them or send a survey to ask them for explicit information to help build your strategy. Most importantly, what is your strategy? What is the promotion you’re going to offer, what channels will you execute on, when are your last delivery dates for posting etc. If you haven’t started to think of all these areas, now is the time to start.

Aside from increasing frequency, what is your top recommendation for standing out in crowded inboxes during the holidays?

Send relevant content to your database - if you’re not already start implicitly profiling your contacts with updated preferences and website behaviour so you can send relevant and personalised emails. You must ensure that the content they receive is relevant to them, for example product recommendations if they’ve only ever purchased woman’s clothing from you don’t send them an email about men’s clothing. Also look at purchase trends - you’re active customers are likely to engage with different content than your inactive customer base, they may also need a different discount level and a different tone for example active customers could have VIP language whereas defecting/inactive we miss you.

How early/when do you recommend brands start their holiday planning? And why?

Planning should begin as early as possible!

We like to start having conversations about Q4/BFCM with clients ad early as June.

Why? Because the lead up to BFCM is just as important as BFCM itself.

There is naturally a decline in sales between August to November. With November being a cashflow heavy period for brands in terms of acquisition budget and COGs, it's important to mitigate this dip in the sales cycle.

We like to Observe historical sales cycles > Look for NATURAL peaks > For valleys we bolster with INTERESTING promos / product launches instead of running an irrelevant sale > We refer to client’s marketing calendar. Prioritise their promotional campaigns (If appropriate. Advise them if it’s not going to do well) > Based on historical trends during those months, we also Increase campaign resourcing accordingly if necessary and adjust goals.

Aside from increasing frequency, what is your top recommendation for standing out in crowded inboxes during the holidays?

Direct Mail has proven efficient especially with churned high LTV customers. We like to run a winback using direct mail before BFCM to bring these people back to the brand.

Beyond that, being creative with merchandising and promotional strategy to create amazing offers that remain profitable during this season.

Let's not kid ourselves, customers are hunting for offers.

If we can create irresistible offers with incremental unit discounting, it means more sales and more contribution margin for the brand.