The Ultimate Guide to Conversational Sales & Selling

conversational sales and conversational selling

The sales landscape has shifted.

We no longer live in a world where companies are the gatekeepers of product information, or where sales teams get to decide how (or when) potential customers get to talk to reps.

With the rise of real-time messaging, and the on-demand economy, buyers have come to expect a new type of sales experience — one where their voices are heard and where conversations happen on their terms.

But here’s the thing:

Most sales & marketing teams still haven’t adapted to this new reality.

Over the past decade, we’ve become so obsessed with driving traffic and generating top-of-the-funnel leads — via content marketing — that we’ve simply doubled down on what we know instead of addressing this fundamental shift in how people research and buy products.

To make up for dwindling conversion rates (according to Salesforce, the average B2B lead-to-opportunity conversion rate is now 13%, while the average opportunity-to-deal conversion rate is 6%) we’ve hired more BDRs, sent out more email blasts, and made more cold calls…

But it just isn’t sustainable.

And if your sales team is starting to feel the strain of constantly having to sort through a sea of bad leads, we feel your pain. The good news is that there’s a new approach that’s perfectly suited to the real-time, on-demand world that we live in now.

It’s called conversational marketing. And the same conversation-driven principles can be applied to sales.

Keep reading for a full breakdown of why conversational sales is the future (and how you can apply it at your sales organization).

Table of Contents

  1. Why Sales Needs to Adopt a Conversational Approach
  2. Conversational Inbound Sales
  3. Conversational Outbound and Account-Based Sales
  4. CQLs & Other Conversational Sales Performance Metrics
  5. Final Thought: Adopting a Conversational Sales Motion


1. Why Sales Needs to Adopt a Conversational Approach

For years, sales and marketing teams have been focused on using the “form and follow-up” approach to capturing and qualifying leads.

We’re all familiar with how this works:

  • Step 1: Drive people to your website (e.g. via content, social, paid ads, outbound email, etc.)
  • Step 2: Make those people fill out lead capture forms
  • Step 3: Email them, or call them, or dump them into an automated “nurturing” flow

For more than a decade now, step one has been getting all the attention, as we’ve been innovating new ways to attract website visitors and track down leads.

Step two, meanwhile, has remained unchanged, and that’s a problem. Because today’s buyers are getting fed up with filling out lead capture forms. As RapidMiner CMO Tom Wentworth explained, the people who visit your website are coming there for a reason (so why waste their time by making them fill out a form?).

People who come to our website aren’t coming there because they want to surf our site, they’re coming there because they have a specific problem, whether it’s a question about our product or what it does, whether it’s some technical support they need, or whether it’s they want to talk to someone in sales.

Using the traditional approach, you would make all of those website visitors fill out forms and then you’d sort them all out later — including the folks who were interested in talking to sales.

But as more and more companies (RapidMiner included) have started to see, by adopting a conversational approach, and engaging with website visitors in real-time, sales reps can create a fast lane for their best leads.

Think about it: With the old way, you’re forcing leads to hurry up and wait. You’re investing all of this time and energy getting leads to your site, but as soon as they get there, BAM. You put up a lead capture form — a barrier.

With conversational selling, you pull down these barriers and give your company’s best leads a direct, real-time line to your sales team. You give leads the power to reach out when it’s convenient for them, and — with the help of intelligent chatbots — you can answer their questions and schedule demos 24/7, 365.

As a result, your sales cycle becomes shorter (example: ThriveHive has seen their sales cycle shrink by 63% after adopting a conversational approach), and you add to your sales pipeline (example: conversations have influenced 25% of RapidMiner’s open sales pipeline, worth more than $1 million).

Ready to see how Tom and thousands of other companies have been using conversational selling to supercharge sales? Keep reading below.

2. Conversational Inbound Sales

With the rise of search engines and social media came inbound sales, a strategy that’s focused on attracting potential customers to your website and guiding them along a buyer’s journey. On this journey, a potential customer typically goes through an awareness stage (I have a problem), a consideration stage (this looks like a promising solution), and finally, a decision stage (this is the solution I want to use).

As an inbound sales team, your job is to educate these potential leads and make sure they have all the information they need to make an informed decision. “Helping is the new selling” is the motto that many of today’s inbound sales reps live by.

But unfortunately, 86% of the 433 sales teams we looked at in our Lead Response Survey lock up resources behind lead capture forms, which means that instead of engaging with inbound leads and helping them in real-time, most sales teams are demanding contact info and then promising to follow-up later. But that follow-up isn’t guaranteed.

In our survey, we found that more than half (55%) of sales teams took 5+ days to respond to new leads, or they never responded at all. Just 7% responded within five minutes, which is what all sales teams should be striving for. Because research shows if you wait ten minutes, your odds of qualifying a lead drop by 400%.

lead response survey data shows a need for conversational selling

These days, more and more buyers (9 out 10, according to Twilio) want to learn about your product by having real-time conversations on your website. And thanks to the rise of messaging and intelligent chatbots, inbound sales team can now deliver that conversational experience at scale.

Here’s how it works:

Step 1: Replace lead forms with conversations

Know that “Contact Sales” link on your website that directs people to a lead capture form? That’s the perfect place to start.

Think about it: There are people coming to your website who are ready to talk to sales and ask questions about your product and how it can help them. By directing those potential customers to lead capture forms, you’re basically tell them, “Meh, you’re not that important to us. We’ll decide later if we want to talk to you.”

Now, imagine if a brick-and-mortar store operated the same way, and the store’s salespeople refused to help shoppers or answer their questions in real-time, while they were right there, in the store …

That’s exactly the type of terrible buying experience we’ve been providing.

The solution: Replace your site’s lead capture forms with conversations.

replace lead capture forms with conversational sales

Instead of having that “Contact Sales” link on your site send people to a lead form, have it open a messaging window so your sales team can start a conversation immediately. Because if you’re not able to answer a buyer’s questions right away, they’ll go looking for those answers somewhere else — like a competitor’s site.

Of course, with so many visitors potentially landing on your website, it’d be impossible to have your sales reps carry out real-time conversations with every new lead. Even sales reps need to sleep, after all. Plus, not everyone who clicks that “Contact Sales” link is actually a good fit for your product.

But don’t worry: Chatbots have got your back.

Step 2: Target your website’s high-intent pages with chatbots.

Chabots can help make your sales funnel more efficient in several different ways.

With intelligent routing, for example, bots ensure that leads automatically get routed to the right reps based on sales territory/Salesforce ownership.

And with intelligent responses, bots can answer the basic questions you’ve already written help docs for — that way reps can focus on answering the more complex questions, which require a human touch.

But for a sales team, the biggest breakthrough chatbots offer is their ability to qualify inbound leads, 24/7.

In just a few minutes, a single rep, or BDR, or marketer can set up a chatbot that asks the same qualifying questions your sales team asks (e.g. “What brought you here? What are you thinking about using our product for?”)

Pro tip for getting started: Target your high-intent pages first, like your pricing page.

You can even configure it so the chatbot only appears to visitors who have visited your pricing page a certain number of times, or who have been looking at it for a certain number of seconds.

Unlike a lead form, a chatbot can capture and qualify a lead in a single step, during a single conversation. It’s a fastlane for your best leads.

The next step? Connect those qualified leads with your sales team.

Step 3: Schedule demos ‘round the clock (even when reps aren’t online).

Using the traditional approach to inbound sales, scheduling demos with leads often required playing phone tag and/or going back and forth in email chains. It was a huge drain on sales productivity.

Thanks to chatbots, reps no longer have to deal with tedious tasks, like trying to coordinate and schedule meetings with dozens of leads. And on the other side of the equation, inbound leads no longer have to deal with all those emails and phone calls — they can book demos instantly.

With just a few clicks, a lead can find an open time on a rep’s calendar, and then a chatbot can take care of sending meeting invites to both sides. And all of this can happen from within the same messaging window a lead began the conversation in.

chatbots enable 24/7 conversational sales

And while chatbots can schedule demos and meetings for reps while they’re offline, when those reps are available, they can easily share their calendars during a conversation.

Reps can also set up and share their profile pages, where leads can drop by and schedule meetings and/or start new conversations.

Wondering how this new, conversational approach to inbound sales has been working? Just ask Scott and Kevin from TrainedUp, who were able to book 80 sales demos in a single month.

3. Conversational Outbound and Account-Based Sales

At Drift, we’ve spent the past year helping salespeople have more conversations with qualified leads on their websites. But we’ve also recognized that websites aren’t the only place where sales conversations happen.

Ultimately, using an outbound sales playbook — in addition your inbound sales playbook — is the best way to ensure your sales team is having all of the conversations that are worth having.

Recently, account-based marketing and account-based sales have been surging in popularity. The approach flips the inbound sales funnel on its head, and puts an emphasis on identifying and reaching out to specific accounts that you already know will be a good fit.

integrating account-based marketing with conversational sales

It’s outbound, but it isn’t “spray and pray” — it’s personalized (e.g. sending a target account cupcakes with their company’s logo on them).

One issue that arises with this approach, however, is that when someone from a target account lands on your website, they get the same experience as every other visitor — and that’s not good.

Remember: These are accounts that you hand-picked. They’re the best of the best. So when they come to your site to look around, you should be rolling out the red carpet for them.

Here’s how to do it:

Step 1. Set up personalized welcome messages for target accounts.

Imagine if every time someone from one of your target accounts visited your website, they saw a personalized welcome message.

Thanks to data enrichment solutions (e.g. Clearbit), that’s now possible. Even if it’s an anonymous visitor, someone you’ve never had a conversation with before, you can see which company that person works at, and then use that company name in your welcome message.

advanced visitor targeting enables ABM in conversational selling

Of course, if calling out the name of the company an anonymous visitors works at seems a little too…well, creepy, you can use that info in other ways.

For example, if Nike was one of your target accounts, and a visitor from Nike landed on your site, your welcome message could say something like, “Sports apparel brands like Reebok and Adidas are using our product. See the results you’re missing out on…”

Instead of delivering the same-old, on-site experience for target accounts, you can use messaging to roll out the red carpet and prompt people to engage in a personalized way.

Step 2. Connect outbound email to real-time messaging.

Of course, the staple channel of outbound prospecting is email. But as we’ve already established, today’s buyers don’t respond to email like they used to.

And that’s mostly because A) too many companies have abused it, and B) more and more people are turning to real-time messaging instead.

That being said, email isn’t dead. (You checked yours this morning, right?)

So instead of giving up on outbound email, we need to bring it into the modern era. And that means connecting email with the rest of the conversations happening on your site.

At Drift, our sales reps always include links in their emails that triggers real-time messaging — so if a prospect opens an email and wants to immediately have a conversation, that conversation is one click away.

And to make the transition from email to real-time messaging as seamless as possible, we make sure the rep who sent the email is the same rep who appears in the messaging widget.

conversational selling across email and messaging

And if the rep who sent the email isn’t available, no big deal: we use our virtual assistant to keep the conversation going.

conversational selling across email and chatbots

No, email isn’t a real-time channel. But by connecting it to one, you can make sure sales conversations with your target accounts don’t get buried in your inbox.

Step 3. Get alerts whenever a target account visits your site or opens an email.

No more missing out on conversations when your prospects are ready to have them.

With the help of a browser extension, you can now get updates as soon as a prospect opens one of your emails or sends you a real-time message.

browser extension enables conversational sales

When sales reps see these notifications, they’ll have the opportunity to reach out and engage prospects in real-time, even if it’s a simple: “Hi there, need any help?”

From a buyer’s perspective, it’s like having a personal shopper at their beck and call. If a question arises, they know there’s someone around to help them.

That’s the type of experience sales should be delivering to their target accounts.

4. CQLs & Other Conversational Sales Performance Metrics

conversational sales metrics

Now that you have a basic understanding of how conversational sales works, it’s time to explore how to measure conversational sales performance.

Ultimately, sales teams end up using a lot of the same metrics they’ve always used, with a few notable exceptions (we introduced CQLs to offer a new perspective on qualified leads).

But let’s start with the most fundamental metric of all when it comes to conversational sales: conversations.


How many sales conversations has your team had?

At Drift, we look at this on a weekly and monthly basis. We see conversations as the fuel that drives the entire business.

Emails Captured

Anytime someone enters an email address during a conversation, a conversational sales platform can capture it automatically.

That’s how lead generation works when you don’t use lead forms: It all happens through conversations.

But to be honest, “emails captured” isn’t as important of a metric to us as this next one…


When we first adopted our conversational approach to sales, we realized that metrics like marketing-qualified leads (MQLs), sales-qualified leads (SQLs), and product-qualified leads (PQLs) didn’t accurately describe what we were seeing.

So we decided to create a new metric: the conversation-qualified lead, or CQL.

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In short, a CQL is someone who has expressed intent to buy during a one-to-one conversation with either A) an employee, or B) a chatbot.

As a sales rep, you can mark someone as a CQL manually, or you can have bots qualify visitors and then mark them as CQLs automatically (assuming they fit the qualifying criteria you set).

Meetings Booked

How many conversations resulted in leads scheduling demos with sales reps?

That’s another important metric for us here at Drift, as well as for thousands of other teams (including TrainedUp).


Now we’re getting back into familiar sales performance metric territory.

Opportunities are potential future sales. It’s not simply about finding someone who’s a good fit for your product, it’s identifying a real revenue opportunity.

When it comes to measuring conversational sales, we look at the opportunities that were sourced from our conversational sales platform.

Pipeline Created

Pipeline created refers to the total dollar amount associated with the opportunities that were sourced from conversations.

(FYI: At TreeRing, their sales team saw a 10% increase in sales pipeline value after two months of using a conversational approach).

Closed Won

How many of your opportunities turned into actual deals? That’s the question “closed won” answers.

It refers to the total dollar amount associated with opportunities (sourced from conversations) that closed into customers.

5. Final Thought: Adopting a Conversational Approach to Sales

The sales landscape is shifting, but we’re here to help you adapt.

And truth be told: making the switch to a conversational approach isn’t all that difficult.

For starters, you can integrate a conversational sales platform with all of the tools you’re already using (Salesforce, Marketo, etc.).

In addition, you don’t have to dismantle your old lead forms and automation sequences: You can leave your old system in place and simply add real-time conversations as a “second net” — a new channel for sourcing net new leads.

Finally, if you’re just getting started with conservation-driven sales, start small. Remember: a single BDR can schedule meetings for dozens of reps. So before trying to make everyone at your company adopt this new approach, prove the value of it first.

And if you have any questions along the way, feel free to reach out.

See why thousands of businesses are using Drift to generate leads and close deals faster.