The 2025 holiday season is unusually short, with just 27 days between Thanksgiving and Christmas. That’s 32 days down from 2024. That compressed window, combined with record-breaking consumer spending and early promotions, is great news for small businesses. But if you’re not ready to capture leads, answer inquiries, and deliver standout service around the clock, you’re leaving a lot of money on the table.
In 2026, this trend toward tighter timelines, earlier shopping behavior, and customer expectations for 24/7 service will most likely continue. That’s why this guide is packed with data-backed strategies for the holiday shopping season and examples of how Ruby makes it all a breeze.
1. Make your move: capture pre-season demand.
Why it matters:
Shoppers are starting earlier than ever. In a 2025 shopping report, 64% of consumers said they planned to start holiday shopping before Halloween, and 49% would begin in October or November. That means the “holiday rush” now starts before Black Friday weekend. For small businesses, this shift opens a golden window to build connections, nurture leads, and get ahead of the big-box competition.
Tip: Begin updating your customer service experience as early as possible so your receptionists and support teams are ready to:
- Promote early-access holiday offers
- Inform customers of seasonal hours or closures
- Answer product or gift-related questions
How Ruby can help:
Custom script updates:
Add early bird promotions and limited-time deals directly into Ruby’s phone and chat scripts.
Live chat lead capture:
Ruby’s chat specialists can collect emails from site visitors and flag high-intent leads before peak season hits.
Lead qualification workflows:
Set custom tags or questions that help Ruby identify high-value leads early, so your sales or service team can prioritize them before the season peaks.
2. Extend your hours (without burning out).
Why it matters:
Today’s customers shop whenever inspiration strikes. Late at night, during lunch breaks, or on weekends, they expect fast answers and seamless service. If your phones or chats go unanswered after 5pm, you’re likely missing out on valuable sales and lasting relationships.
Tip: Add after-hours and weekend coverage through the New Year to meet demand during non-traditional shopping times.
How Ruby can help:
24/7 coverage:
Ruby’s virtual receptionists can pick up after hours, on weekends, or during holidays.
No burnout:
Let Ruby handle late-night queries while your internal team stays rested and focused on core tasks.
Live updates and notifications:
Stay informed in real time with message alerts and summaries through Ruby’s mobile app.
3. Spruce up your scripts for the holiday season.
Why it matters:
During the holidays, customers are more likely to call with questions about promotions, return policies, or availability. If your answering service uses outdated information, it can lead to confusion, frustration, or lost sales. Or if AI answers the call, they might go to the competition for a human response. With the right scripts and friendly, live receptionists, you’ll be unstoppable.
Tip: Audit and update scripts to include:
- Current sales and promotions
- Shipping deadlines and return windows
- Holiday hours and closures
How Ruby can help:
Holiday-ready FAQs:
Ruby’s team can answer seasonal questions like “Do you offer gift wrap?” or “Is it too late to ship by Christmas?”
On-demand script updates:
Easily update scripts through Ruby’s dashboard or with the help of your account manager.
Human-first interactions:
Ruby’s receptionists deliver the warm, personal touch shoppers need during a stressful season.
4. Build your overflow plan before the rush hits.
Why it matters:
The holidays bring a surge in customer activity—from last-minute gift questions to appointment requests and shipping updates. Even the most organized small business can struggle to keep up. And a single missed call can mean a lost sale or a frustrated customer who won’t try again. Having overflow support makes sure you catch every lead, no matter how busy your day gets.
Tip: Add overflow support for peak days, like Black Friday or Cyber Monday.
How Ruby can help:
Smart overflow routing:
When your internal team is busy, Ruby steps in and answers on your behalf with friendly virtual receptions.
Lead capture:
Every call is logged, key info is collected, and hot leads are escalated, making growth easy.
Scalable service:
Add or remove coverage as needed, no hiring headaches or rigid contracts.
5. Share your holiday deals using live chats.
Why it matters:
Live chat is a direct channel to boost holiday sales. When customers see offers in real time while browsing, they’re more likely to act immediately. And the numbers back it up: live chat can lead to a 48% increase in revenue per chat hour and a 40% increase in conversion rate.
Tip: Add a live chat option to your website to:
- Promote gift bundles and exclusive offers
- Answer common gift-related or shipping questions
- Reduce cart abandonment
How Ruby can help:
24/7 chat coverage:
Ruby’s agents can handle inquiries while you sleep, keeping you rested and on top of your game.
Chat-to-call escalation:
If a question gets complex, Ruby can initiate a call or schedule a follow-up with ease.
Brand alignment:
Ruby receptionists interact with customers on live chats to reflect your brand’s tone and act as a seamless extension of your team.
6. Protect your work–life balance.
Why it matters:
The holidays can stretch small teams thin, especially with extended hours, increased foot traffic, and online orders. Trying to answer every call or chat in real-time can quickly lead to burnout, slower response times, and inconsistent service, all of which can impact your brand and bottom line during the busiest time of year.
Tip: Outsource routine call handling, FAQs, scheduling, and payment info, so you and your team can maintain that work/life balance.
How Ruby can help:
Overflow management:
When your in-house lines are busy, Ruby instantly answers overflow calls. This means less stress for your team and happier customers.
With Ruby + Zapier you can set up your trigger, like a call answered by Ruby, and have it automatically update your CRM, email platform, or project management tool.
Ruby guides callers to your secure payment portals or tools, helping ensure smooth and timely transactions.
7. Learn, grow, and glow every holiday season.
Why it matters:
Too many small businesses fly blind when it comes to customer service performance. Without clear data, it’s nearly impossible to know what’s working, what’s falling short, or where you should invest more effort. During the high-stakes holiday season, skipping this step means you risk repeating the same mistakes year after year. Stay ahead of your competitors by measuring and optimizing.
Tip: Set clear KPIs and measure:
- Live call answer rate
- Lead conversions from calls/chats
- Post-holiday returns or satisfaction rates
How Ruby can help:
Robust reporting dashboard:
Track metrics, like call volume, outcomes, and FAQs handled.
Actionable insight:
Adjust promotions or staffing on the fly using real-time data.
Long-term planning:
Use Ruby’s 2026 holiday insights to prep smarter in 2027.
What resources are available for small businesses?
In the US, small businesses have tons of great resources to tap into. The U.S. Small Business Administration (SBA) offers free support, SCORE connects you with experienced mentors, and local chambers of commerce and online training programs are there to help you grow.
These days, staying competitive often means going digital. From marketing to scheduling to customer service, the right tools can make all the difference. And when it comes to talking with customers, live answering services like Ruby are total game-changers. We answer calls, capture leads, and keep your customer service running smoothly—so you can spend less time worrying about missed calls and more time growing your business.
Ruby: the holiday answering service for small businesses
In a compressed and competitive holiday shopping window, small businesses can’t afford to miss a call. Ruby’s human-first answering service, available 24/7/365 and tailored to your brand, helps you scale customer service, capture more leads, and reduce stress, without hiring seasonal staff or sacrificing quality.
With Ruby, you get:
- Early shopper readiness
- After-hours and weekend coverage
- Holiday script customization
- Overflow and chat support
- Real-time data tracking
Make this your best holiday season yet. Let Ruby help you deliver the kind of service that turns seasonal shoppers into lifelong customers.
