Conversational Sales Development Using LiveChat + Chatbots

Tom has been in the sales and marketing world for a decade and offers a track record of delivering results for commercial, social, and non-profit organisations. As the VP of Marketing at CloudTask, he’s helped lead a team that’s generated 450% growth over the past 2.5 years.

Chatbots and live chat are part of the newest wave of sales automation – and for good reason. They are proven to help convert the traffic on your website into tangible leads and opportunities.

It’s a new, low risk/high reward way to create inbound leads and capture information without having to execute cold outreach or put any leads through a call cadence. 

Live chat software is a huge upgrade over the old method of driving your website traffic to a form fill out because it presents your visitors with more open-ended options. 

Instead of filling out a drawn-out form for a single piece of content, they can now do everything from ask a question, to book a meeting, while also deciding whether they want to converse with a live person or a chatbot.

Near limitless possibilities means there are near limitless ways to customize your chat function to suit your organization. But this also means you’re going to have a lot of questions while getting everything set up. 

What’s the best chatbot? How does chatbot marketing work? When should a live person take over for the chatbot? That’s just a few of the many conversational marketing questions that are dominating the conversation.

Before You Start

Before you dive headfirst into conversational marketing, there are several things you need to know to be successful. It won’t be as simple as purchasing a chatbot and turning it on. 

Buyers Have Changed

Modern buyers spend significantly more time researching a product independently before connecting directly with the seller. 

When they finally do connect, they want to be contacted on the channels they prefer and can quickly and seamlessly learn more about potential vendors.

This shift in buying philosophy means that conversational marketing and chatbots are becoming a major asset for sales teams. They help improve efficiency when connecting with buyers and represent a channel most people are comfortable using.

Speed to Conversation

When a buyer is in-market, the speed at which companies can contact those leads has a huge impact on their overall engagement and the ability for them to win that sale.

With Chatbots, SDRs can instantly connect in a conversation and generate immediate meetings and qualified appointments with prospects live on your site.

That instant connectivity wasn’t there in the past and represents a huge shift in the SDR role and how it can be leveraged.

Simplicity for Buyers & SDRs

Not only has this initial conversation increased speed, but it’s also increased efficiency. Prospects no longer have to fill out a form and wait for a call, and SDRs no longer have to wait around for a prospect to respond to their outreach or accept a meeting invite.

The more seamless and simple you can make it for the buyer to connect about your solution, the better your conversion rates will be and the faster you’ll be able to close deals.

The Skills Behind Conversational Development

The good news for any SDR who has recently been given responsibilities around conversational marketing is that they likely already have many of the requisite skills to succeed. 

However, that doesn’t mean they’re all set. 

Every channel requires slightly different skills, and chat is no different. Being able to utilize the right skillset effectively will take some work, but it’s worth the time.

A New Role: The Conversational Development Representative

Chatbots are giving rise to the creation of new roles at larger companies that specialize in real-time chat conversations. 

This Conversational Development Representative (CDR) is solely focused on chat follow up and qualification. They can be seen as a type of channel-specific SDR. 

The basics of the CDR role compared to the SDR role are the same. They still have to be engaging, educational, and valuable to the prospect. They still have to be able to build rapport and carry a qualification conversation on their own. 

However, there are a few key skills that CDRs can gain to ensure success when they’re generating conversations and meetings that come through the chat channel.

Response Time is Key

For starters, being able to respond quickly is vital. Prospects today don’t have the patience to sit around on a webpage and wait for a response. 

Even if your CDR doesn’t know the answer to a specific opening question, the ability to quickly and professionally explain that they don’t have the answer but will find it as quickly as possible is required. 

This ensures the chat will stay open at least a little longer and the prospect is kept engaged while your CDR finds the answer.

Messaging on Live Chat is Brief

Another important thing for CDRs to keep in mind is the size of the box in which their chats are appearing on the prospect’s screen. 

Unlike email, the chatbox is narrow and short. You don’t want your prospect to have to scroll to read an individual response. Sending chats that are too large can be an obstacle to moving conversations forward.

While your CDRs messages should be brief, that shouldn’t be confused with making them as short as possible. You still need to keep it professional. That means it should be clear, easy to read, and grammatically correct.

Mirror How Your Prospect Wants to Have the Conversation

An A+ CDR should still be able to put some personality behind their chats. 

Just as an SDR should match and mirror their prospect’s tone over the phone, CDRs can do the same thing in their chats. 

If the prospect chats in a very direct manner, be direct with them. If the prospect chats in a more ‘chit-chatty’ way, your CDRs should follow suit. 

A CDR who shows good capabilities when it comes to active reading and clear messaging in their emails and chats understands this concept well.

Keep The Conversations Focused

The fast-paced nature of chat tends to influence reps to let their guard down while communicating with prospects, but it’s still important to remain wary of a few things.

For example, while you can typically get more questions answered via chat than you can via email, there is still a point at which the prospect will feel overwhelmed and leave the conversation.

Sharing too much information can scare away a prospect as well. Sending a paragraph of product information is for white papers and data sheets, not chat boxes. 

Knowing what information is concise and relevant goes a long way in keeping the prospect engaged in the conversation and interested in your product.

An easy way to stay on track is to keep the goal of your conversation in mind and guide the conversation in that direction. Extraneous details can be useful when used sparingly, but too much focus off-topic can derail what could have been a successful conversation.

SDR Best Practices for Conversational Marketing

In addition to having the right skillset, there are several best practices SDRs should be following to make the most of your chat function. 

Due to the nature of chat, many of these best practices revolve around concise messaging and quick response times. 

An SDR in charge of chat needs to be on top of their responsibilities more than a traditional SDR, otherwise, the results won’t show.

Defining Productivity in Conversational Marketing

For teams with a traditional SDR handling your chat function, managers need to know where it fits in their day-to-day process. It’s usually a new tool, even for seasoned SDRs, and they have to be able to adapt their process accordingly.

Like all new channels you add, managers need to make sure that they’re spending time on this channel efficiently and aren’t wasting too much time on unqualified conversations.

SDRs handling chat need to be able to balance the fact that they always have to be prepared to receive a chat with their ability to do the rest of their outreach.

Your SDRs shouldn’t be twiddling their thumbs waiting for a chat to come in. They need to be productive while simultaneously keeping an eye out for chat notifications because once one does come in they have to be ready to respond ASAP.

Inversely, they also shouldn’t waste time chatting with a poorly qualified prospect when they could be using that time more productively.

If there is a qualification criterion that can quickly disqualify a prospect before the conversation continues, your SDR can avoid wasting time on a long chat conversation that ultimately equates to nothing.

Automation Doesn’t Compensate for Slow Connect Times

The biggest mistake companies make when they take on Conversational marketing is relying too much on bots to engage with prospects in real-time while being slow with their human response.

It’s okay to use a bot to engage and qualify incoming chat leads. It’s acceptable (and often preferred) to have a bot begin your conversation with a prospect. You can always rely on them to respond quickly and concisely because that’s what they’re programmed to do.

The mistakes come from not following up just as quickly with a real person. Chatbots can only take a conversation so far before it needs to loop in a real person, and that person has to be ready.

If it takes too long to answer their questions, most prospects will just close the tab and go to competitors with their inquiry.

Understanding your prospect’s time constraints and having a human counteract accordingly is essential to making chat work for your business.

Chatbots Need Dedicated Support

Chatbots are great for what they are meant to do, but without proper human support behind them, nearly every conversation they have will flame out. 

Dedicated support is vital, whether it comes from an SDR, a dedicated CDR, or another employee. Your chat should never be unmanned during business hours.

As long as whoever you put behind the bot has proper training and treats it as a priority when chats come through, you should have a successful chat function.

If handing this responsibility off to one individual isn’t working or no individual has the capacity, try using routing rules to direct different conversations to different SDRs so that they share the responsibility evenly. 

Every company has people with higher priorities responding to sales chats. None of those people should ever be responsible for the chat. It needs to be someone like an SDR who can adjust their priorities accordingly every time a chat comes in.

As long as you have your team set up in a way that enables them to respond quickly, efficiently, and professionally you will see success.

Chatbot Automation for SDRs

One of the biggest draws to having a chatbot is its ability to automate certain actions that would otherwise consume an SDRs time. 

Increasing sales automation has been a driving force in sales innovation for a while now, but today even the best chatbot will struggle with certain tasks that would be simple for an SDR to accomplish.

Human Conversations Still Rule

AI has cemented its place in our tech stack because it has many uses. It’s already more consistent than humans at initial engagement because you can automate that message and response. Modern bots are also capable of completing the same simple tasks (like high-level qualification and piquing initial interest) as humans without a noticeable dip in quality.

But a bot is never going to be able to understand everything about a prospect’s company, situation, or the real nature of the questions they bring.

Our ability to take in this kind of specific information and process it to determine the best next step is a uniquely human trait. AI is still not able to fully replicate this type of human-to-human interaction.

Personalize the Automated Experience

Because chat functions involve people and AI working hand-in-hand, one key to success is finding where that balance lies. 

Some people like talking to humans, while others would prefer to chat with a bot. If you balance out the two you’ll increase your odds of aligning with any specific prospect’s preference.

However, in this age of personalization and mass outreach, a lot of people tend to dissociate with bots or automated conversations.

To effectively have any kind of conversational marketing, automation still needs to be personalized to the prospect and well-represent your brand.

Instead of having impersonal messaging and making it obvious a prospect is talking to a bot, personalize the experience and make it feel like an authentic conversation.

By having the bot feel personalized you’ll increase the odds of a decent response. For most prospects your chatbot is the first “person” they are introduced to, so ensuring they reflect your brand and your company is a massive part of your first impression.

Supporting SDR Success on Live Chat

For any manager who’s never manned a live chat, adjusting your usual role to aid SDRs with chat can be difficult because you don’t have the experience. 

No need to worry, the experience you have with other channels will still prove beneficial as you work to enable your SDRs to be as successful with live chat as possible.

Conversational SDRs Need Enablement

The good news for managers is that chat is pretty similar to the more established channels, so it’s not a revolution, just an evolution. 

Chat is just one more channel to add to the SDR’s arsenal.

As long as your SDRs are responsive, helpful, and generate meetings using other channels, they should make the transition to chat relatively easily. 

These are skills you should already be looking for in your SDRs so there’s no difference in whom you hire and bring on to your team just because you’re using chat.

The changes you need to make to support SDR success come from smaller differences and adjustments that, when added together, can turn a good chat-focused SDR into a great one.

Conversational SDRs Need Product Knowledge

For example, product knowledge is more important for chat than for email. 

There is such a high emphasis on response time that taking the time to shoot a note to the product team and waiting for their response when you can’t answer a question is more detrimental than normal.

While your SDR doesn’t need to know everything about a product, it’s immensely helpful when they know as much as possible to ensure a more concise, focused conversation.

Training your SDRs on the product or service that they’ll be selling, both on the front and back-end, allows them to prepare for any difficult questions that come in.

Calendar Scheduling Solution

It’s also important to equip your SDRs with other tools that help convert the prospect from a chat to an opportunity. 

Some type of calendar scheduling tool that integrates with your chat allows prospects to choose the time of your meeting. It will automatically show your available time slots in the chat, allowing the prospect to pick whichever one works best for them.

It saves both your SDR and the prospect time that used to be spent sending multiple messages back and forth to find a time that works for everyone’s schedule. 

Use Personalizable Templates

As useful as personalization is, once you have enough traffic it can become a hindrance to an overwhelmed SDR. This is when you can take a page out of email’s playbook and utilize templates to maximize the efficiency of chat without losing too much personalization. 

If any common questions come through chat, those should be the first responses that are templatized. 

Know that there will never be a template for every response, but by making templates for the most common conversations you have you make the entire process more efficient.

Keep in mind, even these templates should leave some room for customization and should always be double-checked before being sent out. As long as you keep the message specific, the template should work for you.

Conversational Marketing Within the SDR Career Path

It’s becoming increasingly common for SDRs to follow career paths that don’t lead to becoming an AE or VP of Sales. 

As the myriad of potential SDR career paths become more prevalent, conversational marketing is beginning to create its own path as a viable ladder to climb from the SDR position.

Conversational Marketing Opens Opportunities for SDRs

Most organizations use the SDR role as their entry-level sales position, from which someone can move up to be an Account Executive, Sales Director, VP of Sales, etc. 

This makes total sense from a high-level perspective. As you move up the corporate ladder you get to move down the sales funnel to closing and then post-closing roles. 

Recently, the fields that a former SDR can thrive in has been growing. Handling the chat function is one of the many skills that translate well into non-sales development roles. 

Customer success, for example, has been adopting chat longer than sales development has. Being able to quickly communicate with customers when they face any challenges with your product is vital to maintaining them as a customer. The skills required to qualify a prospect over chat translate easily over to this type of customer success role.

Live Chat is Great for New SDRs

Chat is also a great way for a brand new rep to begin learning the SDR process. 

It’s less stressful than having a live phone conversation and much easier for a manager or peer to give them advice in real-time regarding the conversation.

Some organizations are using this to their advantage and implementing chat responsibilities into their training and using it as the first channel a brand new SDR learns. 

Chat can be viewed as a hybrid between the quick back-and-forth of a phone call with the technology-enabled email exchange, so a good number of companies see it as an excellent stepping stone for a new hire to get their feet wet and build the foundation of their product and sales knowledge.

Live Chat Expertise Goes Beyond Sales

Sales and sales development aren’t the only areas of a business that can take advantage of chat. As customer retention and happiness has become an increased focus for businesses, smart organizations are increasingly leveraging chat for customer success.

This makes it easy for an SDR to transition to an existing customer-facing role while staying within an organization, allowing the company to retain their talent.

For larger organizations, conversational marketing is getting to the point that there is room for growth into a new role entirely focused on leading a corporation’s conversational marketing and chat-based efforts.

Advice for SDR Managers Implementing Chat

There are plenty of questions running through the mind of a manager who’s implementing chatbots for the first time. While it would be impossible to answer all of them at once, these are some of the most important things to remember as you begin your chat journey.

Ensure Live Chat Has On-Site Technical Support

Make sure someone in the company is there to handle any issues that arise. 

Nothing is perfect, and when your chat starts acting up it shouldn’t fall on the SDR having the problem to fix it. Someone else needs to step in so that the SDR can get back to their day-to-day. 

Use the Data From Live Chat

While a generic chatbot can be set up in a matter of minutes, setting it up for success takes more time. 

You should be using any existing website traffic data you have to customize the chatbot on each page of your site. If you don’t have that data make sure you start collecting it so that you will be able to make those informed decisions as soon as possible.

The good news is that most chat tools, like Drift and Intercom, provide you with metrics on the number of conversations per page, most engaging messages, and other useful data points. These metrics will help determine how you should be customizing your chats. 

By optimizing your bot’s conversation map using the data provided, you can tailor these AI-driven tools to appear more personal and engaging with each specific prospect that chats your website. 

Keep in mind that these are adjustments that should remain ongoing. The most difficult customizations will likely occur during set up, but you need to keep an eye on metric trends over time to make sure nothing is going stale or losing its ability to engage a prospect.


Keeping up with the modern buyer is a necessity for all SDR teams out there, and this evolution in buyer behavior is reflected almost perfectly in how teams utilize chat.

Rather than looking at chat as a revolutionary tool, however, it’s best to look at it as an evolution and adaptation of familiar processes and responsibilities.

This additional tool can help your team capture more leads, more effectively ramp and scale your SDR program, and provide you with another channel to test your messaging.

In the end, the best way to take advantage of chat is to just do it. It’s a simple enough process to set-up and get running, and you’ll never know if it’s for you until you give it a shot.

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