If Christmas is your Super Bowl, listen up: it’s time to build your holiday offers, bundles, ads, staffing, and shipping plans to glide into Black Friday, Small Business Saturday, and Cyber Monday like a pro. The holiday season isn’t just another sales cycle, it’s the biggest chance to make your numbers, strengthen customer loyalty, and set up momentum that carries you into the new year. Whether you’re a retailer, service provider, or ecommerce entrepreneur, the businesses that thrive during the holidays are the ones that start preparing early and plan strategically.
Why Holiday Prep Matters More Than Ever
Tariff pressures could strain your small businesses during this holiday season, when margins are already tight. Increased import costs on goods or raw materials can raise the price of bestsellers, packaging supplies, or shipping. So, you face a tough choice: pass these costs to customers and risk losing sales or absorb them and cut into profits. Tariffs can also cause supply chain delays or force last-minute sourcing changes that disrupt holiday inventory.
Three ways to prepare:
- Diversify suppliers – Reduce risk by sourcing from multiple vendors, including domestic options.
- Build in buffers – Order early and keep extra stock of high-demand items to avoid tariff-related delays.
- Communicate clearly – If prices rise, explain why and highlight the value you’re delivering to keep customer trust.
With rising costs, supply chain challenges, and increased competition customers are more selective than ever. They’re looking for convenience, value, and authenticity. For small business owners, this is both a challenge and an opportunity. Unlike big-box stores, you have agility on your side, you can personalize offers, build relationships, and lean into community loyalty. Preparing your holiday strategy now ensures you’re not just participating in the season, you’re maximizing it.
Anchor Your Promotions Around the Big Three
Holiday shoppers are conditioned to look for deals around three major events, and you should leverage all of them:
- Black Friday – The kickoff for holiday shopping. Even if you’re not a big-box retailer, you can create urgency with flash sales, doorbusters, or limited-time discounts.
- Small Business Saturday – Small Business Saturday was launched by American Express in 2010 to encourage holiday shoppers to support local, independent businesses. Celebrated on the Saturday after Thanksgiving, it quickly gained national recognition, with bipartisan political support, and has become an annual tradition spotlighting the vital role small businesses play in communities. This day created to highlight independent businesses, especially retailers. This is your opportunity to tell your story, encourage customers to “shop local,” and show how supporting you supports the community. Offer exclusive in-store promotions, loyalty rewards, or customer appreciation events.
- Cyber Monday – The e-commerce bonanza. Perfect for online flash sales, digital bundles, and special shipping incentives.
Boss tip: Create a cascading set of offers, start with Pre-Black Friday specials in early November, roll into a customer-appreciation bonus on Small Business Saturday, and finish with an online-only deal for Cyber Monday. This keeps shoppers engaged and coming back for weeks to see what else you got going on.
Build Holiday Offers That Sell
Think beyond simple discounts. Holiday shoppers love bundles, limited editions, and gift sets. Package complementary products or services together at a slight discount to increase average order size. Create “stocking stuffer” offers at lower price points to capture impulse buys.
Don’t forget gift cards—they’re one of the most profitable holiday products, since many go unused or lead to additional purchases. Position them as the perfect solution for “hard-to-shop-for” relatives and promote them heavily both online and in-store.
Promote Early and Often
Customers are making holiday decisions earlier each year. That means you should be teasing offers, dropping hints, and building anticipation weeks before Thanksgiving.
- Email Marketing: Build a dedicated holiday series. Start with teasers, move into previews, and then launch your official Black Friday/Small Business Saturday/Cyber Monday lineup.
- Use Video on Social Media: Use unboxings, sneak peeks, and behind-the-scenes videos of your holiday prep to catch the attention of your followers.
- Local Promotion: Small Business Saturday is the perfect time to lean into community-based marketing. Use flyers, partnerships with fellow retailers or local nonprofits, and cross-promotions with nearby businesses can drive in-person traffic to everyone’s business.
Optimize for Small Business Saturday
Unlike Black Friday or Cyber Monday, Small Business Saturday is all about relationships and community loyalty. Customers shopping that day are actively looking to support businesses like yours.
Make it special:
- Host a holiday-themed open house with music, snacks, or kids’ activities.
- Share your business story, why you started, who you serve, and how you support the community.
- Offer a “thank you for shopping local” discount or freebie.
This isn’t just about the sale, it’s about building long-term relationships with customers who want to support you beyond the holidays.
Get Your Website Holiday-Ready
If your site isn’t fast, mobile-friendly, and easy to navigate, you’ll lose sales. Before the rush begins:
- Test load times, your site should load in under 3 seconds.
- Make sure your mobile checkout is seamless.
- Highlight shipping deadlines and holiday return policies.
- Add a holiday landing page with your top offers in one place.
Figure Out Your Online Ad Strategy, Too
- Your holiday ad strategy can make or break your sales. With competition at its peak, you need a plan that cuts through the noise and gets the right offers in front of the right shoppers. Start by defining your goals, do you want to drive website traffic, boost e-commerce conversions, or increase in-store visits? Then align your budget with your objectives. Holiday ad costs can spike, so allocate more toward high-performing channels like Facebook and Instagram while testing lower-cost options like Pinterest or TikTok if your audience is there.
- Use retargeting ads too to re-engage shoppers who visited your site but didn’t check out and consider limited-time promotions like free shipping or bundle discounts to create urgency. Keep messaging festive, but clear, highlight convenience, savings, and speed.
- Finally, schedule your ads early. Platforms often delay approvals during the holidays, and you’ll want campaigns running before Black Friday and Small Business Saturday. By combining clear goals, smart targeting, and timely execution, your holiday ad strategy will drive clicks, conversions, and repeat customers.
Staff Up and Train Your Team
The holiday season brings bigger crowds, longer hours, and a higher level of stress for both customers and staff. To set your business up for success, don’t wait until November to hire seasonal help. Start the process early so new employees can be properly trained and feel confident before the rush begins. This also gives your team time to gel and work out any kinks in communication and workflow before peak days.
Clear role assignments are critical during high-traffic events like Black Friday and Small Business Saturday. Designate greeters, checkout support, stock runners, and customer service reps so everyone knows their responsibilities. For service-based businesses, plan for increased call volume, appointment requests, and order fulfillment. Make sure you have backup coverage in place for staff absences. A well-trained, adequately staffed team not only delivers smoother operations but also ensures that every customer enjoys a positive, stress-free shopping experience.
Holiday Staffing Checklist
Holiday Staffing Checklist- Hiring & Onboarding
- Post job listings early (September/October).
- Target reliable sources: referrals, local colleges, job boards.
- Screen for customer service skills and flexibility.
- Complete onboarding paperwork and schedule orientations.
- Training & Preparation
- Train new hires 3–4 weeks before peak season.
- Cover customer service, product knowledge, and point-of-sale systems.
- Role-play busy scenarios (returns, complaints, upselling).
- Walk through emergency and safety protocols.
- Scheduling & Coverage
- Build schedules with extra coverage on Black Friday, Small Business Saturday, and holiday weekends.
- Assign clear roles: greeters, checkout staff, stock runners, online order packers, service reps.
- Ensure service-based businesses have phone/email support coverage.
- Rotate breaks fairly to maintain energy and morale.
- Backup & Contingencies
- Have standby staff on call for last-minute absences.
- Crosstrain employees to handle multiple roles.
- Prepare a “floater” to cover unexpected rushes.
- Team Motivation
- Offer shift perks (snacks, meals, gift cards).
- Communicate daily goals before shifts.
- Celebrate wins and keep morale high with recognition.
Shipping and Inventory Planning
If your business ships products, your holiday logistics plan can truly make or break the season. Shoppers have high expectations around delivery speed, packaging, and communication, especially in the run-up to Christmas. Start by ordering packaging supplies, boxes, tape, labels, and protective materials, well in advance to avoid shortages and price hikes. Build relationships with multiple carriers (UPS, FedEx, USPS, or regional services) to compare rates and create backup options in case of delays. Just as importantly, set clear holiday shipping deadlines for guaranteed delivery by Christmas or other key dates. Post these cutoff dates everywhere: on your website, in confirmation emails, across social media, and even on in-store signage. Clear communication not only builds trust but also reduces customer service headaches.
For brick-and-mortar or hybrid businesses, inventory management requires the same level of foresight. Stock up early on proven bestsellers and seasonal items. Track sales trends from last year and lean into products that historically sell out. Use inventory software, or even a detailed spreadsheet, to monitor stock levels in real time and set automatic alerts or reminders to reorder before shelves are bare. Don’t overlook supporting products or accessories that may sell alongside your main items; bundling them together can increase sales while also ensuring inventory turns over more efficiently.
Ultimately, the holiday season is too critical to leave shipping and inventory to chance. A thoughtful plan ensures you maximize revenue, reduce stress, and deliver an exceptional customer experience that keeps shoppers coming back long after the holidays are over.
Engage Customers Beyond the Sale
Holiday shopping isn’t just about making a transaction—it’s about building memorable experiences that strengthen the connection between your brand and your customers. When shoppers feel valued and appreciated, they are far more likely to return after the holidays and become loyal, repeat buyers. That’s why it’s essential to think beyond the sale and add thoughtful touches that foster long-term relationships.
One powerful way to stand out is by including handwritten thank-you notes with purchases. In a digital-first world, a personal note feels meaningful and memorable, showing your customers that you genuinely care about their business. You can also create delight by offering branded freebies for orders over a certain amount. Whether it’s tote bags, holiday ornaments, or cozy seasonal giveaways, these small surprises leave a lasting impression and keep your brand top of mind long after the holidays.
Don’t forget to engage customers publicly, too. Social media shoutouts for loyal customers, photo reposts, or giveaways tied to user-generated content make shoppers feel part of your brand’s community. Beyond boosting engagement, this strategy encourages word-of-mouth promotion that money can’t buy. Ultimately, by going the extra mile, you transform holiday buyers into year-round ambassadors for your business.
Post-Holiday Follow-up
Post-Holiday Follow-upDon’t let the relationship end on December 25. January is when you can turn seasonal shoppers into year-round customers. Follow up with thank-you emails, surveys, and invitations to join your loyalty program.
Offer “New Year, New Savings” promotions to keep momentum going. This is especially important for people who discovered your business for the first time on Small Business Saturday, nurture them into long-term supporters.
The holiday season is your chance to finish the year strong and set the tone for the next one. By preparing early, anchoring promotions around Black Friday, Small Business Saturday, and Cyber Monday, and leaning into both digital and local community strategies, you’ll not only increase sales but also build relationships that last well beyond the holiday season.
Plan smart, execute with heart, and your business can go from simply surviving the holidays to thriving long after the decorations come down. For more tips on how to sell online head over to www.smallbizladyuniversity.com
Leave a Reply