Webinar Recap: Seizing the Holiday Spotlight with Endear, Treet, and Sezzle

Get ahead this holiday season with expert insights on tech, outreach, and conversion strategies that will make your brand unforgettable

Written by

Danielle Bissonnette, Content Marketing Manager @ Endear


The holiday season is approaching, and brands are gearing up for a time of fierce competition. To help retailers stand out and make this season unforgettable, Endear recently co-hosted a webinar featuring insights from our VP of Sales, Casey Drake as well as Jake Disraeli, Cofounder and CEO of Treet, and Jake Springer, Senior Account Executive at Sezzle. They shared valuable strategies and tactics to maximize conversion rates that can set brands apart from the crowd.

Endear's Content Marketing Manager Danielle Bissonnette and VP of Sales Casey Drake sat down to recap the event:

What we know: Retail brands are ready to embrace their tech stack for the holidays

How are retailers preparing for the holiday season when it comes to technology?

Casey: There’s a lot of great technology that brands can use right now to have a great holiday season. The most important thing when deciding what to focus on is, how will it impact customers, and more specifically, how will it help the customer make a purchase?

I was familiar with other BNPL [Buy Now, Pay Later] services, but this was my first time getting introduced to Sezzle and seeing what they’re doing differently. What’s great is that Sezzle is taking the marketplace approach - this idea that by joining Sezzle, brands are also joining Sezzle’s virtual mall and thus get access to the customers who shop directly through the Sezzle app. 

Then there’s branded resale programs like Treet, where brands can craft tailored resale programs that tap into both eco-conscious and price-conscious customers. Offering pre-loved products caters to customers who prefer sustainable shopping, which is getting bigger every year.

Obviously, you also have technology like Endear, where retail teams can reach customers directly and give them personalized insight into what’s in-store and invite them in. All of these options mean brands can build an effective toolbox to meet their customer needs.

The most important thing when deciding what to focus on is, how will it impact customers, and more specifically, how will it help the customer make a purchase?

Casey Drake, VP of Sales at Endear

Master Black Friday Cyber Monday outreach for maximal conversion

When it comes to outreach this holiday season, what are some outreach strategies you’ve seen work well?

Casey: One thing I think is important for brands to consider when it comes to outreach are the shoppers who are price conscious, and the shoppers who are eco-conscious. With this in mind, there are three SMS strategies I’ve seen tailored to such shoppers that work well:

The first is a personalized message for a launch, for example, the Winter Collection Launch. Not only can you make shoppers feel special, but you’re giving both eco-conscious and price-conscious shoppers time to do their research and plan ahead.

The second strategy is the personalized message offering a gift with purchase. This can both engage and re-engage customers, depending on the audience. As well, the holiday season is all about local community engagement and these promos tend to increase overall foot traffic to stores. 

The third strategy mainly piggybacks off the last one, but it’s creative and I’ve seen brands have a lot of success with it, and that’s the Black Friday Cyber Monday promo. For brands, there may be no better promo opportunity than Black Friday Cyber Monday so it's pivotal that the message is effective. My personal favorite is the 12 Days of Deals promo. I've seen this offer increase SMS sign-ups, drives both online and in-store foot traffic, and most importantly, keep brand top-of-mind for shoppers for consecutive days at the most crucial time of year.

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Practical retail strategies to increase conversion this holiday season

What advice would you give brands on how to practically apply these strategies to their holiday campaigns to increase conversion rates?

Casey: The biggest thing brands can be doing this season with regards to Endear is to look at which options customers currently have with regards to how they can buy. Then implement better messaging to make sure customers know this. The biggest mistake I see brands make is that they don’t push customers to take advantage of all the ways they can shop. It’s so important that brands guide them there. 

The biggest mistake I see brands make is that they don’t push customers to take advantage of all the ways they can shop.

Casey Drake, VP of Sales at Endear

Key takeaway: Keep the customer journey frictionless during the holidays

With this in mind, what were the key highlights from the webinar that you believe brands should immediately implement to improve their holiday season strategies?

In today's highly competitive market, eliminating any potential reasons for customers to choose another brand over yours is essential. Brands can achieve this in a number of ways, for example, by offering eco-friendly options like Treet's resale programs and BNPL services like Sezzle's - I think every brand that sells a higher-priced product should offer a service like Sezzle in today’s day and age. And lastly, get a salesperson to personally guide your customers down the journey you want them on. They don’t have to be in store to do this when there’s options like Endear.

Watch the full webinar here.

The happiest of holidays Endear.

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