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May is permission month.
Tax refunds have landed, winter coats are in storage, and your customers have mentally moved on from "should I?" to "why not?" The caution of Q1 is gone. May shoppers aren't budgeting carefully, they're living like summer is already here.
The calendar backs them up. Mother's Day gives them emotional license to spend. Memorial Day frames itself as the official start of something—grilling season, vacation mode, the summer they've been waiting for. Between those tentpoles, you've got Star Wars Day for the pop culture obsessed and Mental Health Awareness Month for purpose-driven campaigns.
May rewards brands that show up with energy, specificity, and a point of view. The ones that do more than acknowledge a holiday. The ones that understand what their customers are actually feeling.
This is your playbook: the dates that matter, the behaviors behind them, the benchmarks worth measuring against, and campaign ideas built for speed.
May's calendar isn't just busy, it's layered. You've got the big commercial tentpoles (Mother's Day, Memorial Day) that drive massive spending intent. But between them, there's texture: Star Wars Day for fandoms, Mental Health Awareness Month for brands with something real to say, Teacher Appreciation Day for everyone who slept on Mother's Day messaging.
Below is the full May calendar. Star the dates where your brand wants to show up. Ignore the rest.
Quick reference: May marketing holidays
All month:
Early May:
Mid-May:
Late May:
May SMS Benchmarks
May Email Benchmarks
May's SMS calendar is contradictory by design. You need to be heartfelt for Mother's Day, irreverent for Star Wars Day, purposeful for Mental Health Awareness Month, and relentlessly urgent for Memorial Day—sometimes within the same week. The brands that execute well across that range aren't the ones shouting loudest. They're the ones that understand context better than volume: when to lead with emotion, when to lean into humor, and when your subscriber just needs you to tell them what's on sale and for how long.
Below are the strategies that move revenue in May—the full playbooks for your biggest opportunities, plus quick executions for the moments worth acknowledging but not overthinking.
Mother's Day is May's biggest commercial moment, but the window to capture it is shorter than most brands realize. Gift shopping starts earlier than you think and it ends earlier too. Brands that wait until the Friday before have already missed the planners. Brands that stop messaging on Saturday miss the procrastinators.
📊 What top performers did last year: Brands that sent 4 SMS campaigns for Mother's Day drove 7x higher revenue per send than those who sent just 1
Volume isn't noise, it's coverage. You need multiple touches to reach shoppers across the entire consideration window.

Why this works:
Gift intent is time-sensitive: Planners finalize purchases by Wednesday or Thursday of the week before. Procrastinators need a nudge on Saturday. If you only send once, you're leaving half your audience on the table.
Curated experiences cut through decision fatigue: 70% of shoppers feel overwhelmed shopping online, often delaying purchases or abandoning entirely. Brands that use conversational gift-finder quizzes in SMS—letting subscribers narrow options through interactive prompts—see a +37% lift in conversion rate. Less friction, more completed checkouts.
Urgency is built in: Shipping deadlines and the emotional stakes of "getting it right" create natural scarcity. You don't have to manufacture pressure. You just have to surface it.
Opt-out options protect your list: Not everyone wants to receive Mother's Day messaging. A one-tap opt-out signals empathy, reduces unsubscribes, and ensures your sends go to subscribers who are actually ready to engage. It's list hygiene disguised as customer care.
Orchestration tip: Start your campaign early (late April) with a gift guide or quiz. Follow up with shipping deadline reminders, then pivot to instant delivery (gift cards, digital products) for last-minute shoppers.
Memorial Day isn't one day, it's a four-day window where shoppers have time, permission, and intent to spend. High performers treat it like a mini Black Friday: early access for VIPs, momentum-building mid-weekend sends, and aggressive final-hours urgency.

Top recommendations for strong performance:
Channel strategy: Use email for personalized recommendations; leverage SMS for urgency and time-sensitive promotions.
Orchestration tip: Send a pre-sale "save the date" message in early May. Launch the sale Thursday with early access for SMS subscribers. Continue messaging through the weekend with product spotlights, flash offers, and urgency-driven final hours alerts. Send one recovery message on Tuesday for non-converters.
Mental Health Awareness Month gives brands an opportunity to do something genuinely useful, not just promotional. The brands that win here aren't the ones who slap a ribbon on a sale. They're the ones who make their subscribers feel seen, not sold to.

Why this works:
Purpose-driven content earns outsized engagement: Subscribers are more likely to save, share, or respond to messages that feel meaningful. Mental health content—done thoughtfully—clears a much higher engagement bar than a standard promo.
You have 31 days to build a narrative: You don't have to do everything in one send. A month-long approach lets you layer educational content, community moments, and a purposeful offer without cramming it into a single message. Spread your touches across the month.
The right offer doesn't have to be a discount: A charitable donation mechanic (10% of sales go to a mental health organization), an exclusive self-care collection, or a subscriber-only wellness resource can perform just as well. And says more about your brand than 20% off.
Authenticity matters here more than anywhere else: If your brand doesn't have a natural connection to mental health, don't force it. Partner with an organization, share resources, or simply acknowledge the month without making it about your products. Subscribers can smell opportunism from a mile away.
Orchestration tip: Kick off the month with an awareness message (no ask, just a resource). Follow with 1-2 mid-month messages that spotlight your products in a helpful, non-pushy way. In week 3, introduce a donation or giving-back offer. Close the month with a thank-you message and one final resource or offer.
Mother's Day (May 10)
Mother's Day is {X} days away 🌷 Shop our gift edit and find something she'll actually love: {LINK}
We know Mother's Day isn't for everyone. Reply PAUSE to skip all Mother's Day messages this year. We'll see you in June 💚
Memorial Day (May 25)
Our Memorial Day sale starts NOW 🍉🎉 Save {X%} through Monday. Early access for SMS subscribers. Shop first: {LINK}
FINAL HOURS: Memorial Day sale ends at midnight. Don't miss {X%} off everything: {LINK}
Star Wars Day (May 4)
The Force is strong with this sale. 25% off sitewide TODAY ONLY. May the 4th be with you: {LINK}
National Teacher Appreciation Day (May 6)
We 🫶 teachers. In honor of Teacher Appreciation Day, we're offering 50% off for educators. You deserve it. Shop now: {LINK}
Europe Day (UK, May 9)
It's Europe Day. A great time to dream about your summer plans. What's your ideal European escape? Reply with a number:
1 – Mediterranean beach
2 – Nordic adventure
3 – English countryside
4 – Historic city break
National Sunscreen Day (May 27)
It's National Sunscreen Day! ☀️🌴 Don't let those sneaky rays cramp your summer vibes. Stock up on SPF essentials with {X%} off all sunscreen. Today only. Soak up the sun responsibly: {LINK}
Email in May is the channel where you can show, not just tell. You're building visual gift guides for Mother's Day, recipe-forward entertaining content for Cinco de Mayo, purposeful re-engagement sequences for Mental Health Awareness Month, and conversion-heavy flash sale campaigns for Memorial Day.

Below are the email strategies that drive revenue in May: fully flushed out campaign ideas for moments that deserve depth, plus single-send campaign ideas for dates worth acknowledging without overcomplicating.
Mother's Day means different things to different people. For many of your subscribers, it's a celebration. For others, it's complicated. Brands that recognize this want to communicate thoughtfully and the good news is, there's a lot you can do to connect with your customers in meaningful ways.
Build a three-segment Mother's Day email program. Suppress opt-outs entirely, send gift-finding campaigns to gifters, and send "treat yourself" messaging to self-gifters. Different audiences, different needs, different campaigns.
When you offer flexibility and choice in how subscribers engage with your Mother's Day messaging, you're not just being considerate. You're creating opportunities to deepen relationships and build trust that extends far beyond the holiday itself.
Why this works:
Opt-out options earn trust: Giving subscribers the ability to skip Mother's Day messaging signals that you see them as people, not just revenue opportunities. That kind of brand behavior gets remembered and rewarded with long-term loyalty.
Curated gift experiences reduce overwhelm and drive conversion: 70% of shoppers feel overwhelmed shopping online, leading to delayed purchases and abandoned carts. Brands using personalized recommendations see a +37% lift in conversion rate. A well-built gift guide—segmented by recipient type, price point, or interest—does the work of a personal shopper at scale.

Self-gifters are a separate audience worth targeting: A significant portion of your list isn't shopping for someone else. "You deserve it too" messaging, sent to the right segment, regularly outperforms generic gift guide emails on conversion. Don't miss this revenue opportunity.
Campaign 1: The Opt-Out Offer (Send: Late April)
Campaign 2: The Gifter's Guide (Send: May 1-3)
Campaign 3: The Self-Gifter Send (Send: May 1-3)
Cinco de Mayo is more than a one-day promotion. It's an opportunity to position your brand as an entertaining resource. The brands that win here don't just offer a discount. They help their subscribers do something: host a party, cook a meal, create an experience. Email is your medium for this kind of content-forward approach.
Why this works:
Entertaining content drives consideration early: Shoppers don't decide to host a Cinco de Mayo party on May 4th. They plan ahead, usually a week or more. A multi-email series that builds anticipation, offers planning help, and surfaces products in context captures intent earlier in the decision cycle.
Recipe and how-to content earns engagement beyond sales: Subscribers save, share, and return to emails that teach them something useful. A Cinco de Mayo recipe email with links to ingredients or cookware performs better than a generic "20% off" blast because it gives shoppers a reason to buy, not just an incentive.
Visual storytelling is email's advantage: You can't build a tablescape in an SMS. Email lets you showcase styled photography, ingredient lists, step-by-step guides, and aspirational lifestyle content that makes shoppers want what you're selling.
The hospitality angle broadens your audience: Not everyone celebrates Cinco de Mayo culturally, but many celebrate it socially. Positioning your brand as the "entertaining made easy" resource opens the door to a wider subscriber base than a purely cultural angle.
Campaign 1: The Party Planning Kickoff (Send: April 28-30)
Campaign 2: The Recipe Spotlight (Send: May 2)
Orchestration tip: Kick off the series a week before Cinco de Mayo with planning content. Follow with recipe/how-to content mid-week. Send urgency-driven last-minute message on May 4th. Close the loop with a post-event UGC request. Use SMS for last-minute reminders ("party starts in 3 hours—order now for delivery"). Email handles the storytelling, SMS handles the urgency.
Why it works: The FA Cup Final is a cultural event for UK audiences. Even casual fans tune in. Brands with sports, hospitality, or entertainment positioning can own the moment with time-limited offers and match-day content. (This can also be applied to the UEFA Champions League Final on May 30)
Why it works: The FA Cup Final is a cultural event for UK audiences. Even casual fans tune in. Brands with sports, hospitality, or entertainment positioning can own the moment with time-limited offers and match-day content. (This can also be applied to the UEFA Champions League Final on May 30)
Campaign idea:
Orchestration tip: Send the email morning of the match. Follow up with SMS at 2-3 hours before kickoff for final urgency push.
Why it works: Baking is therapeutic, social, and highly visual—perfect for email. Sharing recipes and curated product collections positions your brand as helpful, not just transactional.
Campaign idea:
Orchestration tip: Use SMS to drive urgency ("20% off baking essentials today only") and email to deliver the full recipe and visual storytelling.
Campaign idea:
Orchestration tip: Send this on May 25th as a standalone campaign. Use SMS to drive same-day urgency ("Wine Day flash: 25% off all barware today only"). Email handles the storytelling and lifestyle content.
Campaign idea:
Orchestration tip: Send a post-purchase journey that encourages new buyers to snap photos of their projects and tag you on social. Use this holiday as a natural moment to collect UGC for future campaigns.
The brands that use push well in May understand its limitations as much as its strengths. Push isn't for storytelling. It's not for education. It's for triggering action right now. Use it sparingly, target it precisely, and make every notification worth the interruption.
Push excels at urgency. Mother's Day shipping deadlines, last-call gift reminders, and "you left something in your cart" nudges all benefit from push's immediacy. But the key is timing: send too early and it's noise; send at the right moment and it's a helpful reminder.
When to use push for Mother's Day:
Push copy examples:
Best practice: Only send shipping deadlines and cart abandonment pushes to users who've browsed or added items. Mass-blasting "last chance" push to your entire list creates opt-outs, not conversions.
Memorial Day is a long weekend with fluctuating purchase intent. Push notifications are perfect for triggering impulse purchases during high-intent micro-moments: Saturday morning coffee, Sunday afternoon scrolling, Monday final-hours panic.
When to use push for Memorial Day:
Push copy examples:
Best practice: Layer push with SMS and email. Push is your "top of the hour" nudge. SMS is your mid-campaign reminder. Email is your visual showcase. They work together, not in isolation.