Episode 608 Holiday Marketing Preparation and Strategy With Bridget Willard
Show Highlights
The SDM Show, hosted by Rob Cairns, which focuses on various business and marketing topics. In this segment, Cairns and guest Bridget Willard discuss the critical importance of holiday marketing preparation, specifically addressing the year-end buying season that includes Black Friday and Cyber Monday. They debate whether it is already “too late” to plan for holiday sales and analyze the logistical and strategic pitfalls of offering deep discounts, especially for small businesses and the WordPress industry. The conversation also touches on the need for technical readiness for increased web traffic and the fundamental necessity of tracking marketing analytics for effective business growth.
Show Notes
Episode Highlights: Time to Plan is Over
- Urgency of Preparation: Rob and Bridget dive into the crucial timing for holiday marketing planning. Bridget argues that if planning hasn’t started by late October, it’s almost too late, likening the rush to an “avalanche” of holiday events.
- The Church Analogy: Bridget draws on her experience in church ministry, noting that dates and venues for major holiday events (like pageants and breakfasts) needed to be secured as early as July to avoid scheduling conflicts later in the year. This same urgency applies to business marketing.
- The Early Start: Rob notes that the retail landscape, driven by companies like Amazon, has pushed the Christmas buying season earlier, with stores displaying Christmas items as early as the first week of October. Amazon’s creation of Prime Days (recorded as being in early August) has fragmented the traditional holiday shopping timeline.
Black Friday, Cyber Monday, and SaaS Strategy
- Black Friday’s Origin: Bridget explains that “Black Friday” originates from the day retailers historically moved “into the black” (profitable) after selling off their physical inventory. She strongly advises against e-commerce and SaaS companies using it, calling it a tradition for retail.
- The Supply Chain Factor: Retailers plan up to a year in advance due to the global supply network (e.g., months for goods to ship from China to a US port like Long Beach). This is another reason SaaS companies should avoid competing in the same window.
- SaaS Sales Strategy:
- The License Problem: Rob brings up the issue of WordPress product companies putting everything on sale for Black Friday. He references a post by Katie Keith where she cancels and re-buys all her licenses annually for the discount. Bridget agrees this trains customers to see the Black Friday price as the true price.
- Avoid Support Burden: Both agree that major holiday sales spike support requests. Bridget learned from Matt Cromwell that it’s better to have license renewals spread throughout the year for stable revenue and to absorb the support load slowly.
- The “Cheapo” Customer: Bridget contends that Black Friday/Cyber Monday buyers are often “cheapo posts” who are the hardest support cases and may not even know what they want.
- Alternative Strategy: Instead of steep discounts, Bridget suggests offering a free gift of some kind or having a sale on a different, less competitive day.
Technical and Operational Readiness
- Website Must-Haves: Rob emphasizes critical website preparation for e-commerce:
- Security: Ensure security and software are fully up-to-date.
- WordPress Updates: Rob advises holding back major non-critical WordPress updates (like the scheduled 6.9 update in December) until the week between Christmas and New Year’s, or later, as the fourth quarter is a key money-making period.
- Scalable Hosting: Websites, especially e-commerce, must have scalable hosting that can instantly provide more resources to handle traffic spikes.
- Service and Lead Times: Rob shares an example of a custom jewelry client whose Christmas season ends by the end of November/early December due to the necessary lead time for custom work. Businesses must be aware of their fulfillment deadlines.
- Single Point of Failure: Bridget recalls how the charitable platform Classy went down on Giving Tuesday, affecting all users. This highlights the risk of relying on a single platform and the advantage of WordPress’s distributed infrastructure.
Marketing Strategy vs. Tax Strategy
- The Dark Side of Ads: Bridget explains that large companies (backed by venture capital) often invest heavily in holiday advertising as a tax strategy, aiming to show growth to investors and reduce tax liability, rather than a pure marketing strategy focused on sustainable profit for a small team.
- Don’t Follow the Big Guys: Small businesses should not try to emulate the holiday spending of massive corporations like Amazon, as their goals are fundamentally different.
- Measuring Results (The Dart Board Blindfolded Trick): Both express frustration with small business owners who lack basic tracking. They note that many don’t track where customers heard about them (analytics, referral sources, etc.), making it impossible to justify marketing spend.
- Sales, Marketing, and IT Alignment: All three departments must communicate. Sales often makes promises that IT can’t deliver or Marketing hasn’t fully scoped out (e.g., “just add a button”).
The Cyber Monday Revenue Nugget
- Adobe’s 2024 Report: Bridget shares a key statistic for listeners: During the peak hours of 6:00 p.m. to 8:00 p.m. on Cyber Monday, consumers spent $12.5 million every single minute. This illustrates the immense competition a small company faces on this day.
- Personal Goals: The final takeaway is for entrepreneurs to choose wisely: deal with annoying customers and support issues, or enjoy family time and personal goals.
Find More:
- Bridget Willard: bridgetwillard.com
- Free Business Tool: Bridget has a 40-day preparation tool for Giving Tuesday and Cyber Monday on her website under “free business tools.”
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