Holiday Email Marketing: When to Start Your Campaigns and What to Send

The holiday shopping season starts earlier every year, and for small businesses competing with major retailers, email marketing remains one of the most cost-effective ways to drive revenue during the busiest months. The question most business owners ask is simple: when should I start sending, and what should those emails actually say?

Here is a practical timeline and content strategy to follow.

The Timeline: Four Phases of Holiday Email Marketing

Phase 1: Warm-Up (Early to Mid-October)

This is where you are right now, and it is the most underrated phase. The goal is not to sell — it is to re-engage your list and make sure your emails are landing in inboxes before the high-volume holiday period.

Send a “what’s coming” teaser announcing that holiday deals and content are on the way
Run a preferences update asking subscribers what types of products or content they want to hear about
Clean your list by removing inactive subscribers who have not opened in 6+ months

Cleaning your list now prevents deliverability issues later. A smaller, engaged list will always outperform a large, unresponsive one — especially when inbox providers are scrutinizing sender reputation during peak volume.

Phase 2: Build Anticipation (Late October to Mid-November)

Start sharing value-driven content that positions your products or services as holiday solutions.

Gift guides relevant to your niche
“Best of” roundups featuring your top products
Customer testimonials and success stories
Early access or VIP sign-up for your Black Friday deals

Phase 3: Peak Selling (Late November to Mid-December)

This is your heaviest sending period. Black Friday, Small Business Saturday, and Cyber Monday are the anchors, but do not stop there.

Black Friday and Cyber Monday promotional emails (2-3 per event is acceptable)
Last-chance and deadline-driven emails for shipping cutoffs
Flash sales or daily deals to maintain momentum between major events

Phase 4: Year-End (Late December)

Wind down gracefully with gratitude-focused messaging.

Thank-you emails to customers who purchased during the season
Year-in-review content
Early January “new year, fresh start” positioning for services

What to Send: Content That Converts

Subject lines matter more than ever. During the holidays, your subscribers are receiving 2-3x their normal email volume. Use specific, benefit-driven subject lines. “30% Off Everything This Weekend” outperforms “Our Holiday Sale is Here!” every time.

Segment your audience. Send different messages to past buyers versus prospects. A customer who purchased last holiday season should get a personalized “welcome back” angle, while a newer subscriber needs more introduction to your brand.

Keep designs simple. A clean, single-column layout with one clear call-to-action consistently outperforms elaborate multi-section designs, especially on mobile where most emails are now opened.

Managing It All Without Losing Your Mind

The biggest challenge for small business owners is execution. Planning a multi-week email sequence, segmenting lists, and tracking results takes time you may not have. A CRM with built-in email marketing capabilities like SMBcrm can centralize your contacts, automate send sequences, and track which campaigns are actually driving revenue — all in one place.

The Bottom Line

Start now. The businesses that begin warming up their email lists in early October consistently outperform those that scramble to send their first holiday email the week of Black Friday. Even if your plan is simple, having one puts you ahead of the majority of small businesses that wing it every year.