What Ecommerce Marketers Say They’ve Learned About Holiday Marketing From Past Experience [Part 2]


Whether your holiday marketing strategy is already on set-it-and-forget-it mode or you’re putting your final preparations in place, it’s good to keep an eye out for things you can still do to optimize your plans—especially as the competition heats up. 

We recently spoke with entrepreneurs and marketers from brands of all sizes about the lessons they’ve learned from past Cyber Weekends, the strategies they’re using to set themselves up for success this year, and how they plan to keep the momentum going well into the new year. 

Last week, we caught up with some of the speakers who took the stage at Klaviyo:BOS. Missed their insights? Catch up here

This week, we hear from some entrepreneurs and marketers whose businesses tend to buck the trends when it comes to everything from their products, their discounting strategies, and how they approach Cyber Weekend marketing. Read on to hear their insights and advice. 



Rebecca Melsky [RM]: My name is Rebecca Melsky. I’m the co-founder and CEO of Princess Awesome and Boy Wonder. Princess Awesome makes clothes for girls that have themes on them that are usually only on boys’ clothes, so dresses and leggings with dinosaurs, trucks, science, and things like that. Then we recently launched Boy Wonder, which is similarly flipping the script on boys’ clothes, so boys’ clothes with pink, sparkles, colors, unicorns, and things like that.

On learning from past experience: 

[RM]: One of the previous lessons we’ve learned from Black Friday is to have a combination of both a discount on the site as well as a new product that we’re not including at a discount , which helps to bring in new customers who want the sale but then also our repeat customers who are willing to pay full price. Sometimes people will come for the sale, stay for the new product, or come for the new product and stay for the sale.

On keeping sales going year-round: 

[RM]: To keep sales going year-round, we do a variety of different kinds of things. We have new product releases we try to do every two to six weeks that keep our repeat customers coming back. We have segments and flows set up for people who’ve purchased once but who haven’t purchased again with different kinds of discounts so we can try to get them back but without giving away the whole store. We also rely on seasonality because we’re a kids’ clothing store, so back to school. We also have a very nerdy, geeky client base and so Pi Day is very big at Princess Awesome. That’s March 14th for anyone who doesn’t know. We try to combine those things to keep sales going throughout the year.


See how Princess Awesome uses segmentation to grow




Dan Weisman [DW]: My name is Dan Weisman, I work for Ministry of Supply and I’m the vice president of marketing. 

Ministry of Supply makes performance clothing with technical materials. It’s everything that I’m wearing. Everything from your completely casual wear to a full suit. Everything is made better through science. We say that we make scientifically better clothing. Our founders met at MIT. 

A lot of the processes that we use to design and develop new clothes are based on the same types of engineering design that they studied at MIT. We’re also using materials that come from places like NASA, MIT labs, and generally just make for the best clothing out there.

On learning from past experience: 

[DW]: What we’ve learned from previous Black Friday / Cyber Monday weekends is the importance of keeping things simple. That’s our number one learning, particularly as a small business. Generally, when you make things simple, it both makes things easier for us, the team, to execute and also for the customer to understand what it is that we’re doing.

In addition to our website, we run six retail stores in six different cities. We need to train staff in all of those locations on whatever the deal is for the weekend. We need all of those staff to clearly educate the customers on what the deal is for the weekend. In the past when we’ve tried to do things like tiered discounts, it just gets super-confusing and sales suffer as a result.

Last year, our Black Friday / Cyber Monday deal was really straightforward, just 20 percent off everything. It was hugely successful. Everyone knew what we were doing. Everyone was able to execute on it and customers were super happy, or at least we saw that customers were super happy from the way that they purchased our product on the weekend.

On preparing for Cyber Weekend 2019: 

[DW]: This year for Black Friday / Cyber Monday, one thing we’ve added over the course of the year has been a loyalty rewards program. As we get closer to Black Friday / Cyber Monday, a lot of our higher tier loyalty members are going to receive different offers, incentives, gifts, thank yous, and all of those good things that we weren’t able to do as easily before we had that program in place. In the past, we’ve done gifts for best customers and extra benefits, but it involved a lot of manual work and this year that whole system is much more standardized. I think that’s going to lead to a better experience for everyone.

On keeping sales going year-round: 

[DW]: We like to think of ourselves as a seasonless business, which is pretty unusual in the apparel retail space in general. Most people would do basically two big seasonal buys. One for spring/summer and one for fall/winter. We actually spread our development cycle and our buying cycle out basically throughout the whole year. We’re receiving new products monthly. 

Our communication with customers is really just very, very consistent. We’re constantly talking to customers about new product developments that are happening, new colors that are available, also the community itself. We try to do one message to customers every week that talks about what’s going on behind the scenes, either with the company or with our customers. 

An example of that: we do a monthly customer of the month email and blog post, which features someone cool who is a customer and what they do to make the world a better place. It’s one of our most opened emails. It’s something that people often will tell me that they’ve received and they’ve talked to me about different customers. It really does build a sense of community and keep people engaged with the brand and make it feel like what we’re doing matters. I think that basically, just consistent messaging keeps that going. 

One of the things that we do very strictly is that we try not to do discounts ever except for Black Friday. That’s almost just because it’s unavoidable. Not discounting makes it much, much easier to have that consistent conversation with people because no one is waiting around for the next deal. They’re primed to make the purchase when it’s important to them.


See how Ministry of Supply drives growth with meaningful customer relationships




Emily Baird [EB]: My name is Emily. I work for Nuun Hydration. I’m the digital marketing manager and I’ve been there for about five years. 

Nuun Hydration started out as a sports electrolyte tablet. All the electrolytes you need—sodium, potassium, magnesium, none of the excess sugar. Since then, we’ve branched out into four or five different products, including an immunity line, everyday wellness line, and an endurance powder that has the extra sugar you need for long haul workouts.

On learning from past experience: 

[EB]: In the past, we’ve learned that Black Friday or Cyber Monday preparation is just the most important thing. We do it a little bit differently. We close our doors and our web store on Black Friday. We choose to spend the day outside instead. We really focus on Cyber Monday and it’s a pretty big revenue driver for us. We run a traditional discount. Sometimes we offer free shipping, but everyone knows it’s coming so making sure that marketing communication is ready to go, making sure everything is planned out and prepped, has been the biggest thing for us.

In the past, prior to switching to Klaviyo, we weren’t able to segment our marketing in any way, shape, or form. Everyone got every email. This year’s the first year that we’re planning to actually send customized messages to different groups of customers. We’ll see how that goes.

On keeping sales going year-round: 

[EB]: Sales year-round are a weird spot for us. Nuun does not consider our web store to be a main revenue driver. We use our website more for education and community building. Sales aren’t the focus, but obviously they’re part of our revenue. Strategically, we plan out different promotions throughout the year. We try not to do too many coupons, we don’t want to look like a discount brand, but we plan out our promotions about 12 months in advance and then email is the main method we use for promoting them.


Learn how Nuun Hydration has grown its ecommerce revenue by 3X

Stay tuned for more insights and advice from your fellow marketers. Meantime, check out the ecommerce holiday marketing hub for resources to help you have your best Cyber Weekend yet.

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