Preparing your small business for the holidays

‘Tis the season, or is it? It’s no secret, year after year the holidays appear to start earlier and earlier. But, when does the holiday season start? For businesses in the United States, the holiday season is a critical and often lucrative period typically spanning from late November through early January.

The seasonal holidays encompass Thanksgiving, Black Friday, Small Business Saturday, Hanukkah, Christmas, Kwanzaa, and wrap-up on New Year’s Eve and Day. There is such an incredible opportunity during this most wonderful time of year – roughly a six-week period – for small businesses to increase their profits before the books close.  

How do you take advantage of any and all opportunities for your business? Start planning your holiday marketing strategy well in advance to ensure you have enough time to execute all your incredible ideas effectively. This includes deciding on promotions, campaigns, and the type of content you want to create. 

During this time, businesses across various industries can experience increased consumer spending and heightened demand for products and services. But as a small business owner, you may be feeling overwhelmed just thinking about the holiday season. If you’re just starting to make a small business checklist and not sure where to begin, keep reading to learn how to:

• Build a holiday marketing plan and budget for promotions
• Use email, social media, and content to reach more customers
• Optimize your website and instore experience for seasonal traffic
• Motivate and protect your staff during the busy season
• Make sure your small business insurance is ready for holiday risks

Create a marketing plan

The best place to get started is by creating a marketing plan. Let’s face it, without marketing, your business may not stand a chance of sticking out among big box stores when it comes to finding the perfect gift for Grandma. However, if you take the time now to find ways to get your products or services in front of the eyes of your target audience, chances are you’re on the road to seasonal success. Take time to map out all you would like to include in your small business holiday season plans to ensure you have enough time to bring all your ideas to life.

Remember that the key to successful holiday marketing is to create a positive and memorable experience for your customers. Be creative, authentic, and customer-focused in your approach.

When building your holiday marketing plan, consider:

• Key dates and themes: Plan around major days like Black Friday, Small Business Saturday, Cyber Monday, Hanukkah, Christmas, Kwanzaa, and New Year’s.
• Core offers: Decide whether you’ll use percentage discounts, bundles, free gifts with purchase, or loyalty rewards.
• Primary channels: Identify where your audience is most active: email, Instagram, TikTok, Facebook, Pinterest, local events, etc.
• Content calendar: Map out your messages and promotions week by week so you’re not scrambling at the last minute.

Related: How to Maximize your Small Business Profitability During the Holidays

Holiday season budget

Look at your records from past holiday sales and trends. This will let you establish what to repeat, things you want to change, and based on current trends, things you would like to add.

Go into the holiday season knowing where your business stands, financially. If you’ve not budgeted for extra holiday sales, discounts, and advertising, you’ll want to ensure your business can safely offer deals without seeing red (unless it’s festive decoration).

A simple way to approach your holiday marketing budget is to:

• Review last year’s holiday revenue and set a revenue target for this year.
• Decide what percentage of projected holiday revenue you’re comfortable reinvesting in ads, promotions, and creative.
• Allocate budget by channel (email, social ads, search ads, instore events, local sponsorships, etc.).
• Leave a small “opportunity fund” for lastminute opportunities like an unexpected holiday market, popup, or collaboration.

Seasonal holiday emails

Email is a tremendous asset to lean on during the holidays. All those email addresses you’ve been collecting during the year – it’s time to put them to use! Consider offering a special deal to your email subscribers. This can have multiple benefits. First, you have a method to increase your subscriber list by offering savings to your subscribers. Second, email marketing campaigns are the vehicle that can fuel your entire holiday season.

Whether doing flash sale email blasts weekly, or choosing to have one long seasonal campaign, there is a great deal of potential that comes with being in communication with the folks who have already expressed interest in your products or services, your business, and all that you can offer to them. Don’t discount the ability to retarget your email subscribers either. Many email service providers offer retargeting methodology in their platforms. You can see when your users are most actively opening and reading your messages. Use this insight to schedule your campaign sending. 

Also, reward the most active openers and clickers, and for those who may not be opening, test out different subject lines. Remember, this is the holiday season, emotions are already gearing up, lean into that in your subject lines. Offer your subscribers a reason to open, click, and purchase whatever you’re offering.  

Last note on email, be sure you send out a non-sales holiday greeting to your subscribers. Show them how much you appreciate them and their loyalty to your small business and how you look forward to serving them in the year to come. This is such a simple gesture that can have an incredibly lasting impact. Make it interactive, engaging, comical, whatever matches your brand. And don’t forget to add a social share button. Holiday email campaigns have a decent chance of going viral, so it’s worth it to do this small thing that could get your business noticed by a larger audience.

Holiday email campaign ideas for small businesses

A few highimpact holiday email ideas include:

• VIP early access sales for your best customers
• Gift guides by price point (e.g., “Gifts under $25”)
• Lastminute gift ideas with guaranteed delivery dates
• “Best of the year” roundups featuring your most-loved products or services
• Thankyou emails that highlight customer milestones or impact (e.g., how many orders you fulfilled, causes you supported)

Holiday email subject line tips

To stand out in a crowded inbox:

• Use clear value: “Holiday sale: 20% off gifts for…”
• Lean into urgency (without being spammy): “Last day for guaranteed delivery”
• Personalize where you can: add first names or locationspecific hooks
• Test emojis, humor, or holiday puns if they fit your brand voice

Let’s get social this holiday season

Leverage all of your social media accounts to promote your holiday deals and engage with your audience. Use festive hashtags, run contests, and encourage user-generated content related to your products or services. 

Create holiday-themed blog posts, videos, or infographics. Share content that offers value, such as gift guides, decorating tips, or holiday recipes. This can help position your business as an authority in your niche. These assets can and should be easy for your audience to share with their followers, broadening the reach of your small business.

Holiday social media ideas for small businesses

Consider:

• 12 days of deals: Share a small daily promotion or highlight a different product each day.
• Behindthescenes content: Show how you’re preparing for the holidays, packaging orders, or setting up the store.
• Customer spotlights: Feature customers using your products as gifts or in their celebrations.
• Polls and questions: Ask followers about their favorite holiday traditions or products to drive engagement.
• Hashtag campaigns: Create a branded holiday hashtag and encourage customers to use it for a chance to be featured.  

It’s a season of coming together

Seek out opportunities to partner with complementary businesses for joint promotions. For example, if you're a small bakery, you could collaborate with a local coffee shop to offer a "holiday treats bundle."

Along similar lines, look for low-cost ways to reward loyal customers with exclusive discounts or gifts. This can help strengthen customer loyalty and encourage repeat business.

Related: 8 Easy ways to gear up for holiday shopping season  

Paid media can be the gift that keeps on giving

If it’s in your marketing budget, your small business could benefit from using online advertising channels like Google Ads, Facebook Ads, or Instagram Ads to reach a broader audience. These platforms allow you to use targeting options to reach people who are more likely to be interested in your products and services. One paid click could lead to an even more successful holiday season for your small business. 

“Do You Hear What I Hear?” and user-generated content

Yes, of course it’s a catchy lyric from a well-known holiday song, but we’re talking about user-generated content here. It’s wise to encourage your customers to share their holiday purchases and experiences on social media. It is incredible if they tag you and your small business boasting how amazing you are. Be sure to repost these posts to help build trust and highlight your products in action. 

Get your website in the holiday spirit

Take a deep look at your website, especially if your business is primarily conducted via the web. Look into ways to optimize the performance of your site. You can speed up your website by optimizing images, reducing unnecessary scripts, and enabling browser caching. A fast-loading site is crucial, especially during the holiday season when many people are browsing and shopping online.

Not only are people shopping online in droves, but they are doing it primarily via their mobile devices. You want to make sure your website is mobile-friendly. Many shoppers use smartphones and tablets to make purchases, so a responsive design is essential. Also, a good mobile design makes your site even easier to share socially, so it’s definitely worth spending a bit of time and resources in this area.

Review your website's user experience. Simplify navigation, improve the checkout process, and ensure that pages are easy to read and navigate. 

Update your content
Holiday-themed content gives a special touch to your website. Consider adding holiday banners, graphics, and images and allow these elements to elevate your online presence by creating a memorable and festive atmosphere.

It's also especially important to update product descriptions to highlight their suitability as gifts. Be sure to include details like shipping times and return policies. In addition, make sure you keep your site updated with product availability. With this festive time of year comes increased demand. Clearly indicate which products are in stock and available for holiday delivery. Set up automated alerts for low-stock items to prevent overselling. Set the expectations of your holiday shoppers – avoid potential customer services issues by having a plan in place to monitor inventory.

Holiday-specific landing pages are also a great idea. Consider building ones that feature your bestselling or giftworthy products in one place, highlight holiday promotions and shipping deadlines, and innclude clear calls to action like “Shop gifts,” “Book your holiday service,” or “Buy gift cards.” These pages can be linked from your homepage, emails, and social posts, and can help customers quickly find what they need while improving your holiday search visibility.

Check systems and security
Before the holiday rush, ensure that your payment processing system is secure and ready to handle an increase in transactions. Use SSL certificates and other security measures to protect the information of your customers. It almost goes without saying, check your insurance policies to make sure you have cyber insurance and the plan is active – you never know when a cybercrime may occur, so it’s best to be protected.

It’s crucial to keep your contact information and customer support hours updated throughout the holiday season. Clearly communicate how customers can reach you with questions or concerns. If you don’t already have one, consider adding an FAQ page to address common inquiries, such as shipping times, returns, and gift-wrapping options and add information about this page to your emails and social media posts. Details about shipping and delivery should be included on this page, too. Information about shipping options, deadlines, and costs should be clearly visible. Include estimated delivery times for different shipping methods. Depending on your budget, think about offering free shipping or flat-rate shipping during the holiday season to attract more customers.

Test, and test again
Thoroughly test your website's functionality, including the shopping cart and checkout process. Ensure that your website works across different browsers and devices to provide a seamless experience. Set up analytics tools to monitor your traffic and sales. And pay attention to user behavior, conversion rates, and popular products – this information will be valuable come next year when you’re gearing your small business up for the holiday season once again. 

Create a backup
Regularly back up your system to prevent data loss. Ensure that your site's security is up to date to protect against cyber threats. And finally, have a plan in place to address any technical issues promptly, such as site outages or payment processing problems.

A well-optimized and festive website will attract and retain customers during this busy shopping period.

Everyone loves a festive shop during the holiday season

Preparing your brick-and-mortar store for the holidays is essential to create a festive and welcoming atmosphere, attract customers, and optimize sales during this time of year. Think about decorating your store with holiday-themed decorations, including lights, wreaths, menorahs, ornaments, and maybe even a beautifully decorated holiday tree. With holiday tunes playing, create a warm and inviting atmosphere that evokes the spirit of the season. 

Depending on your retail space, you may want to reconfigure the layout to accommodate increased foot traffic and create easy navigation for your shoppers. Highlight holiday displays and feature popular or gift-worthy items prominently. You can use holiday signage, both outside and inside your store, to inform customers of special promotions, extended hours, and holiday-themed events. Attract attention with eye-catching colors, designs, and window displays. 

Stock up on holiday-specific products or merchandise that makes for great gifts. Consider offering special holiday packaging or bundling options. And if staffing and time permits, gift-wrapping services for customers make their shopping experience more convenient.  

Holiday promotions, sales, and discounts are always a welcomed touch to holiday shoppers. Clearly communicate these deals to customers and try to keep the details simple – no one enjoys over-complicated offers! During the holiday season, consider extending your store's operating hours to accommodate busy shoppers. Definitely advertise your extended hours on your storefront, social media, your website – wherever your customers are apt to find you.

Keep close tabs on your inventory to ensure you have enough stock to meet demand. Restock popular items promptly and manage your inventory effectively to prevent overstocking or understocking. Along those lines, also pay attention to safety and security. With increased foot traffic, ensure that safety protocols are followed, and consider hiring extra security during busy periods to prevent theft or disturbances.

One last note: if you have an online store or website, integrate your online and offline operations. Make sure that product availability and pricing are consistent between your physical and digital stores and if they’re not, be sure to make that clear in both places. Consistency is highly valued by holiday shoppers. 

Related: 10 Ways Small Businesses Can Maximize on Last Minute Holiday Traffic

Keep the elves happy with holiday employee incentives

Motivate your staff with holiday incentives, such as bonuses, prizes, or recognition for exceptional customer service. These little gestures show your employees how much you value them and can really improve employee retention and boost overall morale.

Leave your Grinch behind

We all have personal lives and know just how stressful the holiday season can be. As a small business owner, you have the potential to increase your customer base by providing exceptional customer service, both in-store and online. Be responsive to inquiries and concerns and make returns or exchanges hassle-free. 

Related: Small business customer service: why it’s essential for survival

Make sure your business is covered for the holidays

We’ve given you the gift of a holiday checklist for your small business. But one thing we cannot stress enough is insurance – after all, it’s what we’re known for. With that in mind, don’t leave your small business vulnerable during the holiday season. From right about now until the end of the year, week over week you’ll notice traffic, both in-store and online, will be increasing. With more customers, higher inventory levels, seasonal staff, and special events, your risk profile changes during the holidays. Common holiday-related risks include:

• Slip and fall injuries in busy stores or at holiday markets
• Property damage from decorations, displays, or increased foot traffic
• Theft or vandalism with extended hours and crowded locations
• Cyber attacks or payment fraud as online sales spike

The right combination of general liability, professional liability, cyber insurance, and workers compensation coverage can help protect your business if something goes wrong at the worst possible time.  

An important note for artisans and crafters – this is a prime time for holiday markets and shows. Some crafting venues require a certificate of insurance, and Hiscox can help you with this. Don’t miss out on a fabulous festival because you’re uninsured.  

Bottom line: protect your business with the appropriate policies for your line of work. Whether it be general liability, professional liability,  cyber security, or workers comp insurance, drop by our site or contact us today for a custom quote to safeguard your small business during the holidays, and all year through.

Taking important steps such as any and all of the above can help you create a positive and memorable holiday shopping experience both online and in your brick-and-mortar store. This not only boosts sales but also helps build customer loyalty and goodwill, which can benefit your business throughout the year. 

Frequently asked questions

When should a small business start planning for the holidays?

Ideally, you should start planning your holiday marketing, inventory, and staffing 3–4 months before the season, especially if you rely on ecommerce and shipping.

How can small businesses increase holiday sales?

Focus on a strong holiday marketing plan, clear promotions, a smooth website and checkout experience, extended store hours if applicable, and excellent customer service. Email, social media, and local partnerships can all help you reach more customers.

What should be on a small business holiday checklist?

Key holiday tasks include setting a budget, planning promotions, updating your website and instore displays, confirming shipping and return policies, scheduling staff, and reviewing your insurance coverage.

Do I need special insurance for the holiday season?

You may not need a separate seasonal policy, but it’s important to make sure your existing general liability, property, cyber, and workers compensation coverage is sufficient for higher volumes of customers, sales, and events.