Holiday Ideas & Strategies

Boost Holiday Sales (and Customer Satisfaction) by Integrating Customer Service and Conversational Commerce Strategies

David Feng / 9 min read


Get ready to conquer retail’s busiest time of year. Download the complete guide to selling during the holidays online.


Time flies when you’re having fun. 2019 has been a great year for ecommerce so far. Online sales are still expected to soar to $764.8 billion this year. That’s roughly a 12% increase from 2018. And yet, all of this is still just a small part of what’s projected for 2021 across the world: over 2.14 billion online shoppers generating $4.8 trillion in sales. 

Leading the trend and adding momentum to an already fast-moving train are technologies like chatbots, machine-assisted shopping, conversational commerce, and increased freedom for brands to pick top technology apps to boost customer engagement and conversions.

For 2019, we thought we would take a deeper dive with a playbook-style guide covering how to operationalize most of what we talked about last time, with new ideas on how to use customer service automation to boost customer satisfaction and sales.

Months before each year’s holiday season is always a wake-up call for many merchants. To prepare for the rush, new tools are purchased, new staff members are hired and new processes are put into place. It’s an awesome time for growth and an even better time to establish your brand.

To capitalize on the holiday rush this year, while preparing your business for a more optimized customer experience next year, here’s what I recommend:

  1. Actively discuss your customer service operations in a way that is revenue-focused, rather than support-focused.
  2. Consider how customer service fits into your conversational commerce strategy as a means to increase average order value (AOV).
  3. If you use a variety of tools, you need to immediately evaluate how well-integrated they are with your customer service operations.

Focus on Revenue-Based Customer Service

I’ve attended plenty of ecommerce growth conferences and local community events where merchants, platforms, and app developers discuss a wide variety of topics ranging from marketing to inventory optimization, and from 3PL (third-party logistics) to custom photography.

One topic that is crucial to revenue, but often not actively talked about, is how integral a part customer service plays in the revenue equation.

Customer service is a revenue center. Period. Businesses need to start paying attention to how they can increase conversations with customers through thoughtfully integrated experiences as a means to boost conversions and extend customer loyalty.

When you think about ecommerce as a dependent ecosystem of interactions and experiences, the true advantage of a pure DNVB (digitally native vertical brand) or DTC brand compared to retailers is service. And “service,” in the most traditional sense of the word, means conversations, support, feedback and relationship building.

The more conversations you have, regardless of topic and timing, and the more positive experiences you can offer, the more likely you are to make all customer experiences and transactions smoother.

1. Implement and learn Google Analytics now.

Before you can start to measure your business success, you need a tool designed to keep track of important metrics. Google Analytics is a free, powerful and absolutely essential tool to learn for any business owner. Getting this implemented before the holiday rush is a good idea.

2. Find a customer service tool with Google Analytics integration.

Most modern third-party tools nowadays should integrate with Google Analytics natively. Especially for tools designed to increase or optimize engagement and conversions, this is almost a requirement.

Even if the tool you’re using has its own reporting mechanism, it’s important that it offers a Google Analytics integration so you can tie metrics back to other performance metrics that live outside of the tool.

Here’s an example from a live chat solution’s native and automatic integration with Google Analytics. All chat-related activities are reported to your Google Analytics account, so you can see exactly how much customers are engaging with your live chat support process, FAQ articles, and even individual message replies.

pasted image 0 7

3. Identify revenue opportunities.

Months before the holidays, you’ve spent countless hours optimizing your storefront for SEO, load speed and general prettiness.

And you’ve spent even more hours and money on:

  • conversion rate optimization,
  • Facebook ads,
  • Instagram ads,
  • Google CPC,
  • and retargeting.

But did you know that all that time and money you’ve spent might end up going down a drain? That’s a sad story.

To prevent this from happening, you need to invest some time in identifying revenue opportunities for each individual marketing channel. Some questions you should be asking yourself:

  1. Where are our marketing activities happening right now?
  2. What types of messaging are we using to attract customers?
  3. What happens (or should happen) when customers arrive on our storefront as a result of one of our marketing activities?
  4. What is the customer experience like from there on out?
  5. What do we know about the customer that we can use to our advantage?

Revenue opportunities can be difficult to define sometimes, because everything looks like an opportunity. Sooner or later, the line starts to blur. Around the holidays, however, revenue opportunities are more distinct and can be easily targeted.

Most holiday campaigns are geared toward promotions and discounts. This means your marketing activities will revolve around messages like:

  • free shipping,
  • BOGO,
  • bulk discounts,
  • new customer promotions,
  • repeat customer promotions,
  • VIP specials,
  • free gifts with purchase,
  • and urgency-related checkout incentives.

Each campaign should be tied into your holiday promotions and communications calendar, email segmentation and frequency strategies, custom holiday landing pages, and top-selling product notifications using referral links, UTM tags (the method Google Analytics uses to track unique URLs) and other identifiers.

In addition, you need to think about how every campaign and related communications activities impact your customer service.

For example, when you run a specific holiday marketing campaign like a Facebook ad to announce “Black Friday Free Gift With Purchase,” the goal is to incentivize new and returning customers to purchase.

When customers click on your ad and arrive on your storefront, try to formulate a firm and clear understanding of what you expect them to do and what you think they might be expecting. Those are two very different mentalities.

But even when customers click on your ad, indicating intent, it’s difficult to nudge them into a conversion funnel due to differing expectations. This is where customer service comes in.

4. Start conversing.

Because you know where customers are coming from and what they’re showing interest and intent for, starting a conversation with them is the best way to address differing expectations.

Conversations allow you to reset expectations while simultaneously offering a personalized and welcoming shopping experience.

The best conversational tool in modern commerce is live chat. Chat is a great way to build relationships with new customers, especially during the holiday season, because it effectively reduces uncertainty.

According to Forrester, “Site visitors who use web chat are 2.8x more likely to convert than those that don’t. And according to a benchmark study by Bold360 (a LogMeIn company), a buyer who chats will spend 60% more.” These numbers are what you should be striving for this holiday season.

Live chat has evolved beyond a simple widget that customers can use to contact you. Modern live chat solutions like those provided by Drift, Intercom and Re:amaze augment real-time conversations with in-depth customer insights that are powerful enough to move customers from a simple message to a conversion.

The core mentality is that you want to leverage conversational solutions like chat to power commerce.

Plenty of modern customer service tools today will also give you the ability to trigger automated conversations based on where customers are coming from, who they are, and even based on proprietary customer data. These automated conversations give you the ability to offer personalized customer service at scale.

Engaging customers automatically should be the first step you take to increase the ROI of your holiday marketing campaigns, because they prevent revenue opportunities from getting lost in the weeds. Take this opportunity to introduce customers to your brand’s ability to maintain continuity of service wherever they are in their shopping lifecycle.

In the image below, we’re reusing our Facebook example from earlier to show what a customer’s experience might look like if you’ve implemented this properly. In this image, we’re

  1. Showing gratitude for their engagement on Facebook (reminding them of how they got here and adding personalization).
  2. Telling them again about the free gift with purchase  (reinforcing the incentive).
  3. Informing them that this deal is only available for Black Friday and they should take action today (resetting and shaping expectations while adding urgency).
  4. Introducing them to the fact that a team is available to help through live chat (service extension and indicating willingness to help).

An automated message as simple as this one is extremely powerful, easy to set up, and can be your first step into conversational commerce.

Winston and Abby example

Use Customer Service Tools to Increase Your Holiday AOV

Boosting your average order value (AOV) is the single most effective way to increase revenue.

According to Statista, during 2018’s holiday season, U.S. ecommerce merchants saw an average order value of roughly $130.

During Black Friday and Cyber Monday, AOVs rose to nearly $140.

statista study on cyber monday and holiday

5. Use chat automation to offer personalized AOV boosters.

The key to increasing AOV is understanding the customer’s lifecycle as they evolve through every interaction.

Traditional methods for increasing AOV include simple header banners informing customers that they’ll get free shipping if they purchase at least $50. Or, you can manually display messages that they’ll qualify for a free gift if they add more to the cart.

While these methods have been proven to work, they’re easily missed, lack personalization, and cannot be easily measured for effectiveness. During holiday shopping, customers are easily incentivized to increase their order size and become more receptive to being marketed to. You can improve your AOV processes by leveraging automated customer service tools:

  • When customers are looking at product A, tell them that lots of customers also purchase product B.
  • When customers have $30 worth of items in their shopping cart, inform them that they’re just $20 away from qualifying for free shipping or free gifts.
  • When customers attempt to abandon site or cart, alert them that they’re just $10 away from qualifying for other benefits.

In addition to introducing all customers to bundled offers during the holidays, brands should also focus on delivering on-site chat automation to increase new customer acquisition and return customer reacquisition.

6. Make chatbots the cornerstone of your holiday customer service strategy.

Now that you have some chat automation set up for your store, engaging holiday shoppers should be much more scalable.

But what should you do when customers want to engage you?

Our proprietary data suggests that customer service volume starts to increase well before the holiday festivities actually begin, with over 20% of shoppers starting to window-shop and buy before November 1.

If you haven’t had time to ramp up resources to help customers answer common questions yet, employing the help of chatbots will help increase customer satisfaction, reduce response times, and boost AOV all at the same time.

winston and abby example 2

In a recent study by Statista, over 60% of users between the ages of 25–40 prefer interfacing with a chatbot to find answers to their questions compared to traditional methods like email or phone calls.

And when our team dug deeper within our own database, we found that in the world of ecommerce, over 35% of customer questions can be answered automatically, simply using a business’s FAQ and help center content.

When you implement a chatbot to assist customers 24/7 during the holiday rush, this can potentially mean a 35% reduction in customer service volume. And if your target market is a younger demographic, it’ll mean they’re having a great experience as well.

Chatbots that leverage machine learning, NLU (Natural Language Understanding), and decision trees are here to stay — and to help you create a more engaging customer experience.

Evaluate Your Tools to Enhance Customer Data Connectivity Throughout the Holidays

Data connectivity and continuity is a major problem for a lot of merchants in general and even more so during the holidays. With hundreds of apps for any given purpose to pick from, business owners can get a headache before even thinking about how their decisions may impact customer service down the road.

While you should be focused on building out conversion funnels from your holiday marketing channels, you also need to pay attention to how an influx of new relationships can be nurtured to become repeat buyers.

For example, when a customer finds you on Facebook in November, you want to make sure you can remarket to them later in February.

Having adequate data enables you to do this in a more streamlined way.

7. Plan ahead.

If you sell on a platform like BigCommerce, you already have a great selection of apps available to help you succeed as a merchant.

Apps like MailChimp, Smile, SMSBump and Re:amaze are all great tools to have in your tool belt. Not only do they integrate with BigCommerce, they also integrate with each other.

When you plan ahead so all your tools can speak the same language, you can effectively reduce repetitive tasks — such as searching for order data, checking newsletter subscriptions and verifying loyalty points — by more than 80%.

That leaves you more time to help customers check out and build valuable relationships.

When the holidays roll around, you’ll have something to be thankful for when customer data is easily accessible and updatable in one place. Here are some great examples of what you can do when all your data speaks the same language:

  • When customers chat with you, instantly add them to a MailChimp list without leaving the conversation.
  • When customers email you, verify and update their loyalty points for Smile without leaving the conversation.
  • When customers text you via SMSBump, automatically add a data point that this customer prefers SMS.
  • When customers chat with your chatbot, they automatically receive order status updates.

8. Tie everything back to revenue.

We’re now ready to see if everything I’ve talked about from steps 1–7 actually leads to more revenue.

For this, we need to go back to step 1, Google Analytics. Because we need to understand how each customer service driven engagement impacts revenue, the first action item is to create goals.

Goals are defined differently for each business, but the most common one is probably when someone places an order.

acme company google analytics example

With your goals in place, you’ll need to learn how to create segments to filter out customers that have performed specific event actions such as clicking on an automated chat message, chatting with an agent or interacting with a chatbot.

Combined with goals, segments will be able to show you a subset of customers that have completed goals.

acme google analytics example 2

Google Analytics is powerful because it allows you to map conditions to goals as well. You should be able to look for specific customer service event actions and filter them out based on the goal you’ve defined.

acme google analytics example 3

If this is a little bit too much to absorb with just a few screenshots, just remember that you want to measure how well each customer service-driven interaction leads to more revenue.

Beyond that, it’s all about experimentation and staying diligent about how you’re mapping out your customer journey. If certain messages don’t work well, get rid of them and try something else.

Have a Great Time

If you’ve read this far, it means you’re serious about preparing for the holiday rush.

More importantly, it indicates a potential shift in perspective about how much value your customer service operations can bring to the table.

While this writeup is mostly about gearing up for the holidays, the bigger picture is ultimately about delivering awesome customer experiences through personalizing your customer service-level engagements.

At the end of the day, you can’t limit great customer service to just the holidays. It needs to be something you progressively improve upon. And while I’m more than happy to update this series each year to add new insights into how you can improve the customer experience through customer service, you need to start somewhere and simply get better over time.

Customer service during the holidays doesn’t have to be scary. Commit to focusing more of your attention on building out the right engagement points, the right experiences, and the right revenue opportunities. Remember, time flies when you’re having fun!

Want more insights like this?

We’re on a mission to provide businesses like yours marketing and sales tips, tricks and industry leading knowledge to build the next house-hold name brand. Don’t miss a post. Sign up for our weekly newsletter.


David Feng

David Feng

David is the Co-Founder of, an Ecommerce customer service helpdesk with chat automation and chatbots built in. He is a serial entrepreneur with 3 startup exit experiences and regularly contributes to the Re:amaze Medium publication at BetterThanSure. You can follow Re:amaze on Twitter, Facebook, and Instagram.

View all posts by David Feng

Less Development. More Marketing.

Let us future-proof your backend. You focus on building your brand.

Get ready to conquer retail’s busiest time of year

Unlock proven tips, tactics and expert advice for a successful holiday season.