Conversational Text Messages: Talking Your Way to More Sales

October 11, 2022 Julio Romero

Reading time about 14min


Conversational Text Messages: Talking Your Way to More Sales

Jairene Cruz-Eusebio on Aug 24, 2021 7:05:10 AM

Text messages are among the most effective ways to communicate with your customer. They’re fast, easily accessible, and have a high open and response rate. However, before you can roll out an SMS marketing strategy, you will need to decide how you want to use this technology to communicate with your customers.

Do you want to use SMS to simply inform your customers, or do you want to use it as a way for customers to talk to you, too? If you want to establish a deeper relationship with your customers, then the latter is your best bet.

Table of Contents

What is Conversational Texting?

Advantages of Conversational Texting

Types of SMS Messaging

How to Utilize Conversational Text Messages

Conversational Texting versus Live Chat

How to Improve Your Conversational Texting Strategy

You can keep your messages only one way – from you to the customer – or opt for two-way messaging, where customers can reply to your messages and engage in one-on-one communication with a customer service representative.

This option is known as conversational texting. Properly used, it can be an amazingly effective way with which to communicate with your consumer base.



What is Conversational Texting?

Text messaging has become a big part of our daily life. We use it to chat with friends, get in touch with clients, and even order pizza! But conversational texting is not the same as regular text messaging.

Conversational texting is a way to take your SMS marketing strategy to the next level. By opting for this method of communication, you will no longer be simply sending out bulk, automated text messages that your customers may choose to ignore.

Instead, you allow customers a space in which they can communicate with your team and your brand, allowing you to create rapport and build lasting connections. Additionally, because all conversational texting is a phone with SMS capability, it is far more accessible to customers than other real-time communication methods you may employ, like chatbots and live chat options on your website.

Unlike regular text messages, conversational texts can be long and conversational in nature. You may want to ask for someone’s opinion on your latest product launch or remind them about an upcoming event they might have forgotten about previously.

This way of communicating gives you the opportunity to help your customer solve any problems they may be having, offer them extra information about something they are interested in purchasing from you, or simply ask them how their day is going. In short, it gives the impression that a real person is behind the business, making your brand relatable and approachable.



Advantages of Conversational Texting


Some of the advantages of opting for conversational texting include:

  • Customers can respond at any time and are not forced to decide whether or not they engage.
  • Research indicates that conversational texting offers 20% higher customer satisfaction (CSAT) than voice channels.
  • There is 95% channel retention and a 50% decrease in associate attrition.
  • Messaging is fast, offers personal communication opportunities, and is easy to use.
  • One-way messaging has a 1-2% conversion rate, while conversational texting offers an eye-popping conversion rate of more than 10%. This makes it one of the best-performing marketing strategies available to you.
  • Conversational texting drives deeper relationships between customers and brands and allows you to build long-term relationships. Additionally, research found that communicating with customers over messaging apps helps businesses offer promotions and products that customers are genuinely interested in. This, in turn, makes it more likely that customers will build a personal connection to your brand and have brand loyalty.
  • Messages are more likely to get responses, as the interaction seems natural and value-oriented. This is true even when chatbots are used. With conversational texting, the customer’s needs are addressed directly, which results in them being more engaged in the conversation.
  • As conversational texting results in customer response, you have the chance to collect data directly from them. They let you know what they need in their words, which can be a unique source of essential customer data.



Types of SMS Messaging


There are two main types of SMS messaging: one-way text messaging and two-way text messaging.

One-Way Text Messaging

One way messaging allows you to send out a message and then move on, never expecting or waiting for a response. This is the type of text marketing most often used by companies who want to broadcast information in short form without having to interact with anyone when they reply back.

One-way texting is an excellent option if you’re looking to provide a customer with information but do not anticipate a need for them to respond to the same. Some examples include sending a shipping update and notifying them of an upcoming sale.

This form of communication has its place in certain marketing situations, like sending out marketing materials or reminders about upcoming events. Businesses are able to make better use of one-way text messaging when using personalized SMS messages.

This type of messaging typically shows “Sender does not support replies” to indicate that the user cannot respond to the message. Furthermore, the reply option is usually disabled.

Two-Way Texts Messaging

While one-way text messaging prevents users from responding to messages, two-way text messaging actually encourages them. Another name for two-way messaging is Conversational Text Messaging.

This type of messaging is similar to conversing with someone in person; you’re able to establish more of a personal connection and have an ongoing, two-way conversation.

This makes it easier to reach out to previous customers who might not be following you on social media or reading the email newsletters sent by your company via email. It likewise encourages open communication between businesses and their clients without having to wait until someone replies back after receiving automated texts from your company.


Two-Way Text Messaging Options

Now, let’s diver deeper into two-way communication. Currently, there are two main kinds available for businesses, and this includes:

1. Automated Response (SMS Chatbot)

SMS Chatbot is a practical choice if customers are unlikely to need detailed help. Some uses of this option include confirming appointments, joining or unsubscribing from waiting lists and messaging databases, and responding to special offers.

With automated responses or bot messaging, a customer’s responses are limited. Hence, it should not be used in situations where you anticipate a customer will need detailed assistance.

Conversational texting chatbots are specifically designed and coded to offer value by engaging in two-way communication with your customers. Where SMS chatbots are essentially blunt tools that send out message and notification blasts, conversational texting chatbots are more sophisticated.

However, like all chatbots, these can only shoulder a limited section of what your entire marketing strategy should be. At some point, there is a good chance that the conversation will become too sophisticated and complex for the chatbot. This may be from either the customer’s side or yours. No matter which it is, this is when one-to-one conversations come in.


2. One-on-One Messaging

This is the more complex of the two. It allows you to have long conversations with your customers over text messages, regardless of whether your brand uses human customer service representatives, chatbots, or a mix of both. If and when chatbots are used, the interactions are thoroughly scripted to ensure the conversation sounds natural, and the customer doesn’t realize that they aren’t speaking to another human.

Some examples of situations in which conversational texting can be effective include troubleshooting requests from the customer to your business, review requests from your business to the customer, and issues requiring technical help.

It can also be effective if your product requires you to help customers choose a personalized result. For example, if you run a travel agency, conversational texting allows you to help customers make a decision on where they want to travel, what hotels they want to book, and what their travel itinerary should be.

One-to-one conversations are headed by real humans, usually customer service executives. They take the time to have a detailed discussion with the customer on the other end of the text message thread, understand the situation, and offer thorough, personalized advice and recommendations that a chatbot may not have been able to. They also add human warmth and connection to the conversation and play a major role in building a long-term relationship with customers.


How to Utilize Conversational Text Messages

Now that you’ve seen the potential of using conversational text messaging, let’s discuss how you can actually use it in your business.

Step 1: Sign up for an SMS Marketing app

How can you expect to start your conversational text messaging marketing strategies if you don’t have a business app that supports SMS marketing? There are several of these types of apps available in Shopify, but the best one we recommend is WinBack.

WinBack is a simple yet powerful SMS marketing app that allows you to create automated SMS marketing campaigns within your Shopify dashboard. It will enable you to personalize messages, follow up customers post-purchase, and, most importantly, create custom replies, which is what you would need for two-way text messaging.

Installing this app in your Shopify store is a breeze. All you have to do is visit the WinBack app page, then click on the “Add App” button. Accept the access requirements, and that’s it! You’re ready to use the app.

Step 2: Create your Automated SMS Marketing Campaigns

The SMS Marketing campaigns you should create using your app of choice strongly depend on what you want to achieve.

If you are going for a campaign with automated responses, you first need to create an SMS flow. You must first start with simple SMS flows so as not to confuse your customers and yourself. You can create more complex flows once you gain experience.

To make it easier to demonstrate, let us work on a 3-choice SMS flow.

Let’s say you have an online gift store and you want to help your new SMS subscribers narrow down to specific collections (parent, child, and partner).

SMS Autoreply Flow

Your automated reply must follow a simple flow of if-then-else configuration. Let’s say you want to set up a conversational campaign for three main collections in your store.

You have new subscribers whose interests you don’t know yet, but you want to encourage them to buy from your store with a tailored message.

Here is a simple flow you can create.

First Message: Welcome message with choices

Hi {first name}! As a thank you for signing up at {store}, we’re giving a $10 on your first purchase. Reply with PARENT, CHILD, or PARTNER for a list of gift products. Text STOP to unsubscribe.


The words PARENT, CHILD, or PARTNER (and even STOP) are trigger keywords. Each keyword prompts a different response from the chatbot.

Second Message: Reply based on keyword

Great choice! Here are some of the most popular gift choices from the {KEYWORD} collection. Click on this link to view the collection {link}. Text STOP to unsubscribe.

If your SMS marketing app will allow you, include images in your response to further entice users to visit your website.

A good example of this is the keyword campaign templates we discussed in our Father’s Day Templates, where users are given the option to choose a specific line of products.

Aside from being able to personalize offers, you can also use this conversational text campaign to segment new subscribers based on their interests.

Use Two-Way Automated Messaging for Customer Service

Another way you can use conversational text messaging is to encourage users to send you a message in case they encounter any concerns with the product you are selling.

Example text template:

Thank you for your purchase from {store}! We hope you enjoy using the product as much as we enjoyed creating it for you. If you need any help, just send HELP to 29741. Text STOP to opt-out.



Step 3. Set-up One-on-One Messaging

Aside from automated text messaging, you can of course use person-to-person messaging to interact with your customers. You can use it for promotion, though one of its biggest benefits is improved customer service, which leads to better customer satisfaction.

For instance, instead of automating the response to a HELP reply, you can respond directly to your customer.

WinBack SMS Messaging has this direct-response feature in its arsenal. If a customer responds to one of your messages, you will receive the reply and you can continue the conversation using your email or the Shopify app.

Not only will you be able to provide assistance to your customers quickly, but you can also encourage them to be loyal customers of your brand. With this, you can even increase your Customer Lifetime Value.


Conversational Texting versus Live Chat


If you have a live chat option on your website, you may feel that conversational texting is a different route to the same goal – long-form written communication with your customers that happens in real-time.

However, this can’t be further from the truth. Here’s why:

  • Availability

As covered above, the advantage of text messaging is its convenience for your customers. Live chat features usually require your customer to access your website.

This means that if you want to reach customers via live chat instead of conversational texting, your website must be optimized for mobile usage. Additionally, your customer must have uninterrupted access to the internet.

  • Who Initiates the Conversation

A live chat conversation must be instigated by the customer. With text messages, on the other hand, your business can initiate the dialogue just as quickly as the customer can.

For example, you can send a message asking for feedback on a product that the customer bought from your store. This allows them to continue the conversation and gives them space to ask any questions they may have but wouldn’t have used your website’s live chat to speak to you about.

  • At the customer’s own time and pace

When receiving a text message, the customer can decide whether or not to respond to you. They can take as much as they want—even hours—before they send a reply.

With live chat, the customer is required to respond in a timely manner, or else the live chat may close on its own or may automatically disconnect from the conversation after some time. There is a sense of urgency that sometimes customers don’t care for when seeking assistance.

  • Business representative’s tone of voice

Another difference between live chat and conversational messaging is the tone used during the conversation. Live chats are usually more rigid and depend on easily identified chatbots at the beginning of a session.

Conversational texts, on the other hand, are more authentic and more personal. Consumers believe that there’s a human on the other end of the texts they receive, which allows them to be more genuine in their messages.

  • No data lost

With live chats, if your customer accidentally closes the chat window, the session is ended, and all information exchanged is lost. Conversational texting doesn’t have this drawback, and customers can stop and restart sessions at their convenience.

While live chats undoubtedly play an essential part in any website’s marketing strategy, they are not replacements for conversational texting. Though both conversational texting and live chats require two-way interactions, they are definitely not the same feature.


How to Improve Your Conversational Texting Strategy

While conversational texting can be effective, you will see the most significant benefits if you optimize your strategy as much as possible. Some considerations to keep in mind include:


1. Don’t Forget about Consent

Consent is an integral part of any SMS marketing strategy. Unlike live chat and even email marketing, text message marketing involves the use of a customer’s private data in the form of their mobile phone number.

In order for customers to be confident in trusting your business with this data, they will also need to trust that, should they request it, you will delete their information from your databases.

Additionally, numerous laws around the world require companies to ask customers for consent before texting them. In the EU, this law takes the form of the General Data Protection Regulation (GDPR).

Per the GDPR, not only will you need to ask a customer for consent before targeting them via SMS marketing, but your business will also need to:

  • Provide an opt-out option that allows customers to withdraw consent at any time
  • Anonymize all the data collected via SMS marketing efforts so customers cannot be identified
  • Send customers automatic notifications in the case of a data breach.

Depending on the type of business you run, you may also want to consider including other disclaimers that may be necessary. For example, if you run a business adjacent to the legal profession, you must add a disclaimer stating that you do not provide legal assistance.

On the other hand, if you sell hockey equipment, you likely won’t need to include any disclaimers in your message scripts.

Before embarking on any SMS Marketing campaign, make sure you read our article on SMS Marketing Compliance to make sure you are following all legalities.


2. Add Value

Like any other marketing strategy, conversational marketing should be able to add value to your customers’ interactions with your business.

This means you should contact them only when you think a two-way conversation with them can be meaningful to their needs.

Also, you should tailor your strategy depending on customer segments as much as possible.

For example, if a customer has ordered something from your shop, you should wait until the following happens before requesting a product review:

  • The product has been delivered;
  • The customer has had a chance to use it (thus, a few days post-delivery).

Contacting them immediately after the order was placed will almost always be an ineffective use of conversational messaging and will likely only annoy the customer.

You can also use segmentation to ensure that your choice of conversational messaging is as effective as possible. For example, you may choose to segment customers based on time zones. This will allow you to contact customers at the optimum time of day, rather than at times where they will be unavailable, such as in the middle of the night.

Plus, sending them a message in the middle of the night can cause them to be irritated at the sound of a text message that is not even an emergency.


3. Address Customers by Their Name

As mentioned above, one of the main reasons that conversational texting is an effective marketing strategy is that it allows customers to connect with your brand at a personal, human level.

To ensure that your strategy offers this type of one-to-one connection, it’s essential that you converse with each customer like a unique person rather than a faceless entity.

One easy way to do so is to address them by their first name, especially at the start of a conversational texting session. While including their name in each message will make the conversation seem stilted and forced, peppering it in throughout the conversation can be effective.

The added benefit of this type of personalization is that it is not limited to human-to-human conversational texting. Even if your conversational texting strategy involves the use of chatbots, you can build the personalized address into the script that you teach the bots.


4. Keep the Conversation Flowing

Conversational texting is meant to be a two-way exchange, which means the conversation between both parties should flow naturally.

Following the creation of a text thread, you can then take your cues from your customer, changing your questions and tone to match theirs.

If you’re using a chatbot, make sure you have an alert that lets an employee take over the conversation if questions become too complex for your script to answer. This reduces the likelihood that the customer will realize they weren’t talking to a real person and help keep the conversation flowing.

Additionally, make sure to ask questions that are personalized to your customer and that you can offer tailored responses to.

For example, if you run a high-end jewelry business, you may ask customers what segment of jewelry they are most interested in, which metal the pieces should be in, and which precious stones they prefer. Based on those answers, you can then direct them to tailored recommendations or offer them unique deals that add value to their experience shopping with your brand.


5. Be Approachable but Maintain Professionalism

While conversational texting has its benefits, it also has its own unique drawbacks. One of the biggest challenges with text marketing is texting trends – as trends change, you will need to be careful about your language.

Keeping language on-trend may help attract a younger generation of customers, but it may turn away an older audience at the same time.

One solution to this challenge is using segmentation effectively. Additionally, you will need to be careful about the type of language you use in your texts.

It’s also important not to be too informal with those on the receiving end of conversational text messaging. After all, this form of communication still requires some level of professionalism for it to work well. Therefore, stick with formal language when necessary and avoid using abbreviations like “lol” or typing in ALL CAPS if possible.


6. Keep it Short and Simple

This is age-old advice that is still very much useful in this scenario. Even in an extended marketing option like conversational texting, it’s recommended to keep messages as short as possible without interrupting the natural flow of conversation.

Remember, your audience’s attention span is limited, and you need to make sure you get the most out of the time you do have with them.

Furthermore, if you’re adding links to your message, keep the actual URL as short as possible, and make it clickable.

There are many link shortening applications you can use, and shorter links mean that more of the customer’s attention will be directed to the actual text of the message.

To learn more about this, visit our post on Shortening Links in SMS Messages.

Finally, try not to send too many messages at once. Keep your messages short, and give the customer the opportunity to reply. Once they reply, you can then continue your conversation.

Unless your customer is actively engaging in a conversation with you, keep the text messages to a minimum.

Ideally, you should send only one or two “message starters” a week, though this frequency may differ depending on your specific business and audience.


7. Have a Call-to-Action (CTA)

Remember, conversational texting is not the only way to connect with your customers; it is also a marketing strategy.

Make sure to include a strong CTA at the end of every message thread so that your customers will know what to do next. In short, lead them into your expected action.

In general, you shouldn’t include more than one CTA per thread, however, as this may annoy the customer. However, this will differ depending on your business and marketing strategy.

A strong CTA:

  • Creates a sense of urgency
  • Is clear and compelling
  • Is concise
  • Provides value and pushes the customer to action

CTAs can be:

  • Promotional, like links to offers, discount codes, coupons, loyalty points, etc.
  • Cross–platform-based CTAs that ask customers to follow you on other platforms like Facebook, signup for a newsletter, etc.
  • Keyword triggers, which encourage users to respond to the actual text message.

Start Connecting with Your Customers with Conversational Text Messaging

Conversational texting is undoubtedly one of the strongest marketing tools available to businesses today. Brands should ensure that if their current SMS marketing strategy does not include a section on conversational text messages, it is added the soonest possible time.

However, like all other marketing strategies, it’s essential to remember that testing is key. If you’re building a chatbot, it will need to be tested via focus groups to ensure your customers will react the way you want.

Even if you’re using human customer service executives to handle your conversational texting strategy, they will need to be trained on best practices to help them build relationships with customers faster and easier.

But if you’re looking for something you can handle on your own, especially if you’re a one-man band when it comes to your business, then I strongly suggest signing up for WinBack. Get the 14-day trial while it still lasts!

Topics: SMS Marketing, SMS Messaging Templates, Best Practices