We’ve all been there.
It’s Black Friday week, and your inbox looks like a warzone. “50% OFF EVERYTHING!” “LAST CHANCE!” “DON’T MISS OUT!” Every brand you’ve ever bought from (and a few you definitely haven’t) is screaming for your attention at the same time.
And what do you do?
Delete, delete, delete.
But seasonal email campaigns don’t have to feel like a desperate pitch. Done right, they can actually strengthen your relationship with your audience, drive real revenue and leave your customers genuinely excited to hear from you, even during the busiest shopping periods of the year.
The secret? It’s not about selling less. It’s about selling smarter.
In this guide, I’ll walk you through proven seasonal email strategies that drive sales without making your subscribers want to hit “unsubscribe.”
Short on time? Here are the key takeaways
- Plan ahead: Map out your seasonal calendar early and mix promotional emails with value-driven content so your audience doesn’t feel bombarded.
- Lead with story: Open with a personal angle, behind-the-scenes moment, or customer story and let the offer emerge naturally.
- Segment your list: Even basic segmentation (new vs. returning customers) makes seasonal emails feel personal rather than mass-blasted.
- Build anticipation, not panic: Replace “LAST CHANCE” energy with early access, limited editions, and countdown sequences that create genuine excitement.
Plan Your Calendar Before the Season Hits
If you’re scrambling to put together a Valentine’s Day email on February 13th, you’ve already lost.
(The same goes for getting your partner a gift, but I’ll save that story for another day!)
The best seasonal email strategies start weeks, often months, in advance. And I don’t just mean pencilling in “Black Friday campaign” on a sticky note. I mean building out a proper content calendar that maps every seasonal moment worth showing up for.
Now, that doesn’t mean you need to email your list for every obscure holiday on the internet (nobody needs a “National Sock Day” campaign. Unless you’re the CEO of Socks ‘R’ Us). But it does mean identifying the moments that genuinely matter to your audience and planning a mix of content around them.
Here’s a good rule of thumb: for every promotional email you send, aim to send at least two that educate, entertain, or inspire. That way, when the sales email does land, your subscribers are already engaged and far more likely to open it.
I call this the give-and-take approach. Each sales email you are ‘taking’ from your audience, offering little support, asking them to take action. Each educational or entertainment piece builds trust, offering readers value and asking for nothing in return.
Psychologically speaking, this makes the reader much more likely to purchase when the sales email does come their way.
Lead With Story, Not the Sale
Here’s something most founders get wrong with seasonal emails: they lead with the discount.
“30% off for summer!” “Holiday sale starts NOW!” Sure, it’s direct. But it’s also exactly what every other brand in your subscribers’ inbox is doing. And when everyone is shouting the same thing, nobody stands out.
Instead, try leading with a story. A personal angle. A behind-the-scenes look at why you created a particular product, or a customer story that ties naturally into the season.
For example, instead of “20% off our summer collection,” imagine opening with something like, “We designed this piece for those long weekends where you want to look good without trying too hard.” The offer can still live in the email, but now it has context, personality, and a reason for existing beyond just shifting stock.
People remember stories far more than they remember sales pitches. In fact, research suggests that people retain around 63% of stories but only 5% of standalone statistics. So if you want your seasonal emails to stick, give your subscribers something worth remembering before you ask them to buy.
The discount is the cherry on top, not the whole cake.
Segment Your Audience for Relevance
Let me ask you something.
Would you send the same Christmas gift to your best friend, your boss, and your grandma?
Probably not. So why would you send the same seasonal email to every person on your list?
One of the fastest ways to make your emails feel “salesy” is to blast the same generic message to your entire subscriber base. It screams, “I don’t really know who you are, but please buy something.” And your audience can feel that a mile off.
Even basic segmentation can make a huge difference. Splitting your list into new subscribers versus returning customers is a great starting point. A first-time buyer might need more of an introduction to your brand during a seasonal push, while a loyal customer might respond better to early access or a “thank you” discount that rewards their loyalty.
From there, you can get more specific. Segment by purchase history, engagement level, or even browsing behaviour. The more relevant your email feels, the less it reads like a sales pitch and the more it reads like something that was written specifically for them.
The good news? You don’t need to be a data scientist to do this. Tools like Omnisend make segmentation straightforward, even if you’re a solo founder juggling a hundred other priorities. A few smart filters and your seasonal campaign suddenly feels a lot more personal than the “Dear Valued Customer” approach.
Create Urgency Without the Desperation
Urgency works. That’s not up for debate.
But there’s a big difference between creating genuine anticipation and making your subscribers feel like they’re being guilt-tripped into a purchase.
We’ve all seen the emails. “FINAL HOURS!” “You’ll regret missing this!” “This will NEVER happen again!” It’s the email marketing equivalent of a used car salesman following you around the lot. And honestly? Most people see right through it.
The good news is you can still create urgency without resorting to the all-caps panic approach. It just requires a little more thought.
Early access is a brilliant example. Instead of pressuring everyone at once, reward your most engaged subscribers by letting them shop before anyone else. It creates exclusivity rather than anxiety, and your audience feels valued rather than rushed.
Limited editions and seasonal exclusives work in a similar way. If a product is genuinely only available for a short window, that’s real urgency, and your subscribers will respect it because it’s authentic, not manufactured.
Lily, the founder of Luu Lounge, nailed this approach. Before her drops went live, she had her entire email and SMS list waiting for the launch date, the time, everything. By the time the product was available, demand had already built. She wasn’t chasing customers with “LAST CHANCE” subject lines; she had them queuing up because the anticipation had been earned through genuine excitement, not desperation.
That’s the kind of urgency that drives sales and keeps people subscribed.
Automate the Heavy Lifting (So You Can Focus on What Matters)
Seasonal emails shouldn’t feel like shouting into a crowded room. They should feel like a well-timed conversation with someone who already wants to hear from you. The founders who win at email marketing aren’t the ones with the biggest discounts or the loudest subject lines; they’re the ones who treat their subscribers like people, not transactions.
That’s exactly what Foundr students are doing right now, building real businesses with email and SMS strategies that work around their schedules, not against them. And with the right tool, it’s a lot more achievable than you might think.
If you want to start building seasonal campaigns that drive revenue without doubling your workload, Omnisend makes it practical. Foundr readers can also get 50% off their first three months, just use code FOUNDR50 when you sign up, and start turning your seasonal moments into your most profitable ones yet.
