Happy Sunday, Fam!

I hope you’re all resting and thriving today!

Last week was a bit of a whirlwind! I spent most of my time in NYC, speaking at Yotpo’s Retention Uncensored alongside my retention bestie, Eli Weiss, and later catching up at the Q4 Ecomm Founders Summit hosted by my DTC homie, Nik Sharma. It was an incredible week of learning, networking, and hanging out with friends and some my clients, Lineage Provisions and Taste Salud, IRL. Definitely one for the books!

But now I am home and writing you from the comfort of my couch in Chicago, and this is truly everywhere I want to be right now so I can talk to you about marketing strategies from my little corner in the digital universe.

In a world that’s constantly competing for our attention, how do you make your brand stand out? That was the core theme in so many of the conversations I had this week at these two conferences. From mastering marketing strategies to breaking through the noise, one thing is clear—gaining and holding people’s attention is harder than ever, but the opportunities for creativity and impact have never been greater.

All of this learning and vibing about marketing strategies this week has me thinking about one tactic I don’t see talked about enough though—sweepstakes & gamification. I’ve seen it used effectively time and time again, but I don’t see us breaking it down for others to use it in their own marketing strategies.

So…as I do…let’s break down the psychology of gamification but specifically sweepstakes.

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Unlock the Fun, Unlock the Sales

There’s many ways to gamify an experience, whether it be through strategies in email and sms, or building applications, but one that I have seen work time and time again in boosting sales and boosting engagement is gamification in sweepstakes.

Gamification has proven to be a powerful tool in driving online engagement. Studies show that customer activity increases by an average of 68% when gamification elements are introduced, and social sharing jumps by 22% in gamified experiences. In fact, engagement metrics can increase between 100% to 150%, making gamification a strategy that not only captures attention but also sustains it, ultimately driving customer retention and conversion.

Now I can tell you first hand working for a brand and the wins that this type of gamification has brought. When I was working at Feastables, one of the most impactful strategies we deployed was an always on “play to win” strategy. (despite me personally having to handle delivering 11 teslas around the country, iykyk) 

As part of our February 2022 launch, we introduced a massive sweepstakes that included various prizes, culminating in the ultimate grand prize—a chocolate factory. 

This campaign wasn’t just about offering prizes; it was a smart way to drive customer acquisition and guide people through our marketing funnel, transforming passive interest into active engagement.

The giveaway leveraged the power of gamification, which taps into the psychology of competition and reward. By offering such a unique prize, we incentivized customers to engage with the brand at multiple touch points—through purchases, email sign-ups, and social media follow-ups. The sweepstakes didn’t just create buzz; it brought people into the funnel where they were exposed to the brand’s broader messaging and products. It gave customers a reason to stay connected beyond the initial interaction, as they were eager to see updates or check their chances of winning.

By tying the giveaway to product purchases and interactions, we converted the initial attention into action. Customers were not only introduced to Feastables but were immediately engaged with the brand by entering the sweepstakes through various means. This multi-channel approach—using social media, email, and SMS—enabled us to optimize the customer acquisition funnel and guide people smoothly from awareness to purchase, and eventually into retention.

This strategy played a significant role in Feastables’ rapid growth. We weren’t just focused on immediate sales—we were building a community. Through consistent follow-up and ongoing engagement with new customers, the sweepstakes generated a loyal audience that we could continue to re-market to through email and SMS campaigns. This retention marketing was crucial for driving repeat purchases, as we created recurring touch points that kept customers connected to the brand.

Through smart gamification, multi-channel marketing, and a focus on long-term customer retention, this strategy helped Feastables scale rapidly while creating a community of engaged, loyal customers. Other brands can learn from this approach by implementing interactive experiences that not only capture attention but also nurture customer relationships.

Gamification in the B2B World TOO!

Lastly, I have also seen an interesting play even in the B2B world with Recharge’s Tomorrow Brand. 

Recharge has successfully integrated gamification into its B2B strategy with the Tomorrow Brand Challenge, which encourages brands to compete for prizes like $100,000 in cash and a $50,000 marketing bet for 2025. Much like Feastables’ sweepstakes, Recharge leverages the psychology of competition to drive customer engagement, acquisition, and retention. By turning business education into a fun, competitive experience, Recharge isn’t just promoting its services—it’s fostering collaboration, networking, and strengthening its brand’s value in the subscription economy.

For B2B brands, gamification is particularly effective because it turns passive users into active participants. Recharge motivates businesses to adopt new tools and strategies by offering tangible rewards, creating an enjoyable learning experience. Both DTC and B2B brands can benefit from gamified strategies by tapping into the psychology of rewards and competition, which helps deepen engagement, boost customer loyalty, and drive long-term growth. Whether through a sweepstakes or a competitive challenge, gamification strengthens customer relationships while moving them through the funnel more effectively.

The underlying success of gamification, whether in DTC or B2B, is that it creates an interactive experience that rewards engagement. At Feastables, this meant giving customers an incentive to keep coming back, while at Recharge, it meant helping businesses engage with the platform in a meaningful way. Both approaches focused on long-term retention, not just one-time interactions.

For DTC brands, gamification can transform a product launch or campaign into an interactive event that pulls customers into the funnel and keeps them there. For B2B brands, gamification can be used to educate, engage, and foster collaboration within the industry, all while driving adoption of key products and services. In both cases, the strategy builds stronger, more loyal relationships with customers by turning marketing into an engaging, rewarding experience.

Key Takeaways from a Gamified Marketing Strategy:

1. Gamification Boosts Engagement: Introducing an interactive element like a sweepstakes can significantly increase customer engagement, leading to higher acquisition rates and more meaningful connections with the audience.

2. Retention Through Multi-Channel Marketing: By staying connected with customers across multiple platforms—email, SMS, and social media—you can build long-term relationships that extend beyond a one-time purchase.

3. Customer-Centric Strategy: By keeping the customer experience at the heart of the campaign, we ensured that the sweepstakes wasn’t just about prizes but about integrating customers into the brand’s story and fostering deeper loyalty.

Well, that’s that for this week and the takes on how gamification can be a really dope marketing strategy if done right.

And as always, if you have any questions or things you want answers to in this newsletter, please hit the “reply” button and send them over or hit that link below for my form!

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Same time, same place next week?

Jess

Have a Marketing and/or CX-related question for me?

UPCOMING EVENTS

1. If you are a brand operator or founder, join me and the Recharge gang at QC Spa on Governors island on October 7th! RSVP HERE

2. Nancy and I are hosting a Customer Service Appreciation week dinner! If you are a Retention or CX operator and in NYC, this one is for you on October 8th. RSVP HERE

3. A FUN AF Shoptalk party. Casino Night for Shoptalk Fall in Chicago on October 16, 2024! RSVP HERE

4. Come to NYC on November 14th for SheInnovates 2! If you are a woman in ecommerce, this one is for you. Grab your ticket ASAP, we are almost sold out! Snag your tickets here.

DOPE JOBS OF THE WEEK…

I posted quite a few roles in Friday’s Dope Jobs post here.

My client Lineage Provisions is looking for a
Social Media & Community Manager.
Apply Here!

And my other client Print Fresh is also seeking a
Senior Retention Marketing Manager.
Hybrid in Philadelphia.
Apply Here!

Yotpo has a VERY great job board here

BEST PIECE OF CONTENT I’VE SEEN THIS WEEK…

@eugbrandstrat

Our culture is stuck in place 🛑. Today’s vid: how our obsession with nostalgia is driving a resurgence in heritage brands with a particul... See more

👐 BONUS CONTENT 👐

MORE GIRLS TO THE FRONT! This week, I released an episode with Lila Sullivan co-founder of Flourish Plants.

Be sure to follow along on my YouTube, Spotify and Apple Podcasts.

A WORD ON THIS WEEK’S SPONSOR

Recharge is a leading subscription management platform that enhances customer retention and drives business growth. With advanced analytics, robust support, and innovative tools, Recharge empowers merchants to create personalized, engaging experiences.

By focusing on the OVERALL subscription journey, Recharge helps brands build lasting customer loyalty and deepen connections, ensuring customers feel valued and appreciated.