According to our Customer Success Managers, May’s marketing holidays are the backbone to setting up your campaigns for success in the summer.

From May Day to Memorial Day, May has some great holidays to center your marketing campaigns around. And as retailers and brands continue to navigate shifting economic tides, the May holidays can be a chance for marketers to help consumers pause, recharge, and reconnect with campaigns that drive engagement and secure brand loyalty. 

But it’s not just the holidays that marketers need to keep in mind this month. We sat down with Jackie Iskyan, Sr. CSM, New Verticals, and Nicole Grauer, Sr. CSM, New Verticals, to understand what’s top of mind for marketers as we head into May.

In this blog, we’ll share actionable advice for creating May campaigns that resonate with your subscribers and drive conversions, how to tap into seasonal moments and build trust, and help you craft marketing messages for the upcoming holidays of Cinco de Mayo, Mother’s Day, and Memorial Day. 

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May marketing benchmarks

We ran the numbers to see how May has changed year-over-year in terms of sends and found that across our bigger accounts, there was a 23.2% increase in total sends comparing May 2024 to May 2023. We saw a 10% greater increase in Journey sends (33.7%) compared to campaign sends (22.5%), meaning marketers were focused on behavior-based messages rather than one-off campaigns last May. This increase in sends led to an increase in revenue to the tune of 37.9%.

We also wanted to look at our data to create these benchmarks for enterprise retail, food and beverage, and entertainment and media industries for their May SMS campaign sends. 

Now that you know what benchmarks you want to hit, how do you get those results?

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Focus on growing and nurturing your lists

Our CSMs note that May has a lot of seasonal excitement as consumers eagerly await the start of summer. Whether promoting new clothing for the new season, new flavors debuting on a menu, or a limited-edition product, May is an opportune month to create a sense of anticipation with your marketing. 

Iskyan, who works with many Food & Beverage brands, shared that May isn’t just the start of summer—it’s the start of grilling season, BBQs, rosé, and more. May is full of food holidays, including National BBQ Month and National Hamburger Month, making it a prime opportunity for marketers to engage and build momentum heading into summer.

If you’ve got big holiday promotions planned, it’s a great idea to launch sign-up units that highlight the offer and activate them a few weeks in advance to build excitement and grow your subscriber list. A countdown timer sign-up unit would work especially well here to drive urgency. 

- Jackie Iskyan, Sr. CSM, New Verticals, at Attentive

Grauer, who works with many travel and hospitality brands, completely agreed on using countdown timers, especially in May, to drive excitement and a sense of urgency. She suggests that marketers should focus on list growth ahead of these major holiday sales. 

She said, “I always recommend A/B testing sign-up units to make sure that my clients are maximizing our list growth tools and capturing the widest audience possible. Through ample testing, my travel clients have found countdown timers to be one of the most effective list growth tools as creating urgency tends to lead to higher opt-in rates.”

‍While building up your list, don’t forget about your loyal subscribers who have been on it for a while. There’s the notion that consumers believe that new customers get the best deals and customer experiences. When asked how marketers can ensure their existing subscribers remain loyal, both Grauer and Iskyan zeroed in on value prop strategies.

One effective strategy is implementing loyalty programs or ongoing incentives, such as personalized birthday messages. By collecting subscribers’ birthdays, brands can deliver tailored, meaningful experiences—like offering a special discount on their birthday—that not only strengthen the customer relationship but also encourage continued interaction and repeat purchases.

- Nicole Grauer, Sr. CSM, New Verticals, at Attentive

Iskyan agreed that it’s all about strengthening the customer relationship and making loyal subscribers feel valued. She said, “For subscribers who’ve been part of your program for a while, consider creating a ‘VIP’ segment. You can build this based on criteria like number of purchases and message engagement. Once identified, treat these loyal customers to exclusive perks—like extra discounts, early access to new products, and special offers—to make them feel valued and appreciated. It’s a great way to build loyalty and strengthen the relationship over time.” 

According to Attentive’s Consumer Trends Report: The State of Personalized Marketing in 2025, 96% of consumers say they’re likely to purchase when receiving at least one type of personalized message—like back-in-stock notifications, loyalty point reminders, or product recommendations based on their last purchases. Consumers want brands to remember their preferences, make relevant product suggestions, and remember their past interactions.

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Take care of your subscribers during Mental Health Awareness Month

May is mostly known for Mother’s Day and Memorial Day, but it’s also Mental Health Awareness Month. And just like asking subscribers if they want to pause messages around specific holidays, it’s a great time to evaluate other ways you can show empathy and support for your subscribers.

Iskyan highlighted using conversational campaigns to ask subscribers about their preferences for receiving messages from your brand—and be transparent about how you’ll use this insight to respect their preferences and send only the content they care most about. 

Grauer again agreed with Iskyan by focusing on content each subscriber cares about most—as well as using conversational messaging to get that insight. She recommends using keyword responses and question prompts, which not only gives you the information you’re looking for, it also allows you to identify your most engaged subscribers and segment accordingly. 

For the travel space, conversations can help brands identify which destinations are the most popular or which time of year customers like to travel the most. This can inform future campaign strategies and optimize SMS and email sends. 

AI Pro is an excellent tool when it comes to targeting the right portion of your audience at the right time. While A/B testing campaigns for content and send time is fantastic and insightful, our AI Pro feature takes the guesswork out of it. It uses each brand’s actual data to help inform when we should be sending campaigns and to which specific subscribers. 

- Nicole Grauer, Sr. CSM, New Verticals, at Attentive

Mental Health Awareness marketing strategies can include:

• Education: Create and share content that educates and destigmatizes mental health issues, such as sharing expert guidance, personal stories, and resources.
• Engagement: Offer special promotions or discounts for wellness products and services, such as meditation apps, fitness classes, or self-care kits.
• Participation: Launch initiatives that encourage open conversations about mental health, such as hosting webinars, Q&A sessions, or social media challenges. 
• Commitment: Partner with or give back to charities, organizations, and initiatives that support mental health. 

By prioritizing the well-being of your subscribers, you can build stronger, more meaningful connections and show your commitment to a healthier, supportive community.

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Graduation celebration campaign ideas

May is filled with food-related holidays and food is always welcome at many celebrations, including graduation parties. Iskyan talked about two approaches for F&B brands to create graduation campaigns. For brands that offer catering, she advised, “You can create a dynamic segment based on location—like city, state, zip code, or even distance from a store—and target subscribers who live near one of your locations. It’s a great way to stay relevant and drive catering orders when people are planning celebrations.”

Brands that sell grilling supplies, snacks, or other party-ready items should reach out early and remind subscribers about the upcoming important celebration and any shipping deadlines.

Offering a discount or providing free shipping for graduation celebrations would incentivize your subscribers and help drive even more conversions. These kinds of campaigns can position your brand as the go-to for easy and delicious party prep!

- Jackie Iskyan, Sr. CSM, New Verticals, at Attentive

Grauer noted that graduation is a valuable marketing opportunity for travel brands as well. She said, “With many graduates enjoying a window of free time before transitioning to their next chapter, such as starting a new job, this period presents an ideal opportunity for travel. Especially when paired with an attractive discount, travel can serve as a meaningful reward. Brands can acknowledge both graduation and the start of summer with a targeted promotional offer.”

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Make your mobile messaging experiences more engaging with visuals

A picture is worth a thousand words. In a channel like SMS where every word counts, sometimes it helps to turn that SMS into an MMS by adding an image or video. With the Cannes Film Festival kicking off on May 13, it got us thinking about using images, GIFs, and videos in mobile marketing messages.

Subscribers tend to engage more with MMS—especially in the F&B space. Since people “eat with their eyes,” featuring a mouthwatering visual or GIF of a new menu item or product can really boost excitement and drive clicks and conversions. 

- Jackie Iskyan, Sr. CSM, New Verticals, at Attentive

Iskyan did note that, “Every audience is different. I always recommend A/B testing to see which type of MMS content—image, GIF, or video—resonates best with your subscribers.”

Now is the optimal time to do testing on MMS as we get ready for RCS Business Messaging. 

Attentive’s Consumer Trends Report: The State of Personalized Marketing in 2025 found that 95% of consumers expressed interest in at least one RCS Business Messaging feature, and 90% said they’re more likely to make a purchase when interacting with at least one of these capabilities. One of those features is the ability to swipe through curated product recommendations with carousels. RCS will be dynamic, visual, and interactive. MMS can help you start building that engagement and interaction with your brand’s messages now.  

Another option for brands that want to use a lot of visuals in their marketing messages is to turn to email more often. Grauer and Iskyan both noted how email is ideal for messages that need a bit more room to breathe or that are graphics-heavy.

Iskyan said, “Combining both of these powerful channels will drive higher engagement and revenue for your brand. Email is ideal for storytelling and educating your audience, as it offers more space for longer copy where you can go into detail. On the other hand, SMS is perfect for timely communications–like last-minute reminders, quick follow-ups, and pushing real-time conversions.”

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May marketing holidays and examples

Lastly, we want to share some upcoming holidays that you can anchor your marketing campaigns around. 

Quick reference of May marketing holidays:

• Asian Pacific American Heritage Month
• May 4: Star Wars Day
• May 5: Cinco de Mayo
• May 5: Early May bank holiday (UK)
• May 6: National Teacher Appreciation Day
• May 9: Europe Day
• May 11: Mother's Day
• May 12: Fashion Event in Australia
• May 13: Click Frenzy Mayhem (AU)
• May 17: World Baking Day
• May 17: FA Cup Final (UK)
• May 19: Victoria Day (CA)
• May 20: Chelsea Flower Show (UK)
• May 25: Premier League Final (UK)
• May 26: Memorial Day
• May 26: Spring bank holiday (UK)
• May 27: Sunscreen Day
• May 30: National Creativity Day
• May 31: UEFA Champions League Final (UK)

Let’s dive into some of the bigger marketing holidays in May that you should build campaigns for—and show some examples of campaigns we love.

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Cinco de Mayo

37% of intended celebrators of Cinco de Mayo only make their plans one or two days in advance. Which is great if you need to turn a campaign around fast. 

This holiday shouldn’t be skipped by F&B brands and Quick-Serve Restaurants (QSRs) as 16% of respondents plan to order food for takeout or delivery. Compare this to Mother’s Day, where people make reservations and dine out. 

Iskyan agreed about this being a popular holiday for her clients. She shared, “We definitely see a lot of alcohol brands and QSRs taking advantage of Cinco de Mayo. It’s a great opportunity to remind subscribers about any special deals happening in store locations or by placing a takeout order for a big group.”

Messaging ideas for ‌Cinco de Mayo SMS campaigns:

• We’ve got your Cinco de Mayo grub needs covered! Pre-order for 5/5 now and secure a free serving of chips & guac and tres leches cake! Order: {LINK}
• Spice up your collection with our Cinco de Mayo sitewide sale! Enjoy 15% off now through May 6. Use code CINCO. Don’t miss out on the fiesta of savings! {LINK}
• ¡Feliz Cinco de Mayo! Take an extra 5% off your purchases this weekend. Shop Now: {LINK}
• Let’s taco ‘bout taking 25% off and $5 ground shipping for our Cinco de Mayo Sale! Use code MAYO5 at checkout >> {LINK}
• Celebrate Cinco de May weekend with a festive sip! Enjoy 5% off storewide. No code necessary. Stock up now: {LINK}
• Final Hours! Celebrate Cinco de Mayo with 15% off all orders over $200. Use code: MAYO15 Don’t miss out, order now! {LINK}

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Mother's Day

37% of consumers plan to go out to eat for Mother’s Day. And 48% said they make plans one to two weeks in advance, and 30% are planning a month or two in advance. Start sending early and often for this holiday.  

Iskyan said that “Consumers are looking for personalized and convenient ways to find the perfect Mother’s Day gift. Give your SMS subscribers early access to shop before anyone else so they can purchase early and avoid the stress of last-minute shopping. Send subscribers a helpful deadline reminder to ensure their purchase arrives before the big day, while also creating a strong sense of urgency.”

Create a gift-finder quiz and prompt subscribers with questions about who they’re shopping for, their budget, etc. This interactive experience mirrors the in-store experience where they might ask a a sales associate for recommendations. It’s an engaging way to guide subscribers towards discovering products that fit their needs.

- Jackie Iskyan, Sr. CSM, New Verticals, at Attentive

Iskyan reminds her clients that Mother’s Day can bring up different emotions for different people. She recommends using Two-Way Journeys to ask subscribers to opt out of anything Mother’s Day related if they wish. It’s a simple way to show your brand cares about your subscribers and their well-being. 

Messaging ideas for Mother’s Day SMS campaigns:

• We understand that Mother’s Day may be a sensitive time for many. If you'd like to pause communications during this holiday, please reply with PAUSE.
• It’s HERE: The Mother’s Day Gift Guide. Shop our curated picks for the woman who deserves them most: {LINK}
• Give her a personalized gift this Mother’s Day with complimentary engraving that will add a unique touch. Place your engraving order by 5pm EST today to ensure on-time delivery. Customize Now {LINK}
• Mother’s Day is fast approaching. Give her the gift that keeps on giving with our mother-approved self-care bundle. Pamper her now: {LINK}
• Gift ready? It’s Mother’s Day in 10 days and we’ve got what she likes at 20% off! Shop our Mother’s Day edit: {LINK}
• Mother’s Day checklist: Get mom a planter ✅ Pick out a bouquet 🌼 Make brunch reservations 🥞 Last-minute gifts here: {LINK}
• Spoil Mom with love: Enjoy 15% off gifts she’ll adore during our Mother’s Day sale. Use code MD15 at checkout >> {LINK}
• Cake is a mother’s love language! Pre-order a special treat just for her: {LINK}
• Who doesn’t want to pick out a new pair of shoes? Gift cards are the perfect way to let mom get exactly what she wants for Mother’s Day. {LINK}
• It’s almost Mother’s Day! Still looking for the perfect gift? Don’t waste any more time, spend $75 now and we’ll give you FREE 2-day shipping {LINK}
• Last day to stack savings! Up to 70% off! Our Buy More, Save More sale is ending and faves are going fast! {LINK}

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Memorial Day

94% of intended celebrators expect to buy something for Memorial Day, and 35% plan to spend more than $100 on the holiday. Snag your brand some of that consumer spending by implementing a multi-touch campaign strategy to maximize engagement and revenue. Both Iskyan and Grauer mentioned how important it is to build up anticipation and excitement about your brand’s Memorial Day sale.  

Iskyan said, “Start with an initial campaign a few weeks in advance to build anticipation and generate early interest. Follow up with a message a few days before the holiday weekend, offering early access to the promotion to make subscribers feel like VIPs.”

In the travel space, Memorial Day Weekend is known to be one of the marquee holiday sales of the year, so it’s important to tailor your campaign messaging strategy in a way that creates build-up in the weeks leading up to the sale. This is a great time to not only tease the upcoming savings they can expect, but to also educate your customer base about new destinations and perks, to retain and engage your subscribers ahead of the sale.

- Nicole Grauer, Sr. CSM, New Verticals, at Attentive

Iskyan also added that you should schedule at least one final message post-weekend to extend the sale, and if possible, capture any last-minute conversions. She suggests that you should incorporate time-sensitive language to create a strong sense of urgency and drive action with these holiday campaigns.

Messaging ideas for Memorial Day SMS marketing campaigns:

• 🇺🇲 Honoring our heroes this Memorial Day with 25% off everything. Limited time offer, shop now: {LINK}
• Why wait until Monday? Our Memorial Day sale is live NOW! Use code MEMORIAL25 for 40% off your purchase. Shop our biggest sale of the season >> {LINK}
• Celebrate Memorial Day with a radiant glow! ✨ Unlock a bonus gift set (up to $150 value) with qualifying orders. Get your skincare routine summer ready. Shop Now: {LINK}
• Save BIG this Memorial Day! Enjoy 20% off everything, automatically applied at checkout. {LINK}
• The Memorial Day sale is happening now! Get up to 50% off everything and enjoy free shipping. Save now > {LINK}
• Happy Memorial Day! Embrace the holiday vibes by shopping our red, white, and blue collections. ❤️ 🤍💙 Tap to unlock an additional 25% off: {LINK}
• Salute to savings! The Memorial Day FLASH SALE is happening now, VIPs! Enjoy 20% off your entire purchase, today only, so stock up for summer now! {LINK}
• Celebrate Memorial Day with our limited edition {PRODUCT}! Only 500 available, so get yours before they’re gone! Shop Now {LINK}
• Surprise! We’re giving you 24 more hours to shop the extended Memorial Day sale. Don’t miss 60% off everything: {LINK} 
• The clock is ticking ⏰  Save up to 25% off for Memorial Day before midnight or wait until next year—don’t have sale FOMO: {LINK}
• ICYMI: Our VIPs get a second chance to shop the Memorial Day sale. Get $200 off until 11:59 tonight. SHOP NOW: {LINK}

Check out our marketing campaign calendar to find key dates for campaigns, orchestration tips across your channels, and SMS templates you can copy and paste.