Why Read This?

This guide is used to deploy conversational sales to your sales development team.

It will answer the following questions:

  • How to introduce live chat to your sales team
  • How to analyze good and bad conversations
  • How to coach your team to have better conversations
  • How to align a sales development representative (SDR) team with account executives and a marketing team

This guide uses the Conversational Framework to inform how to engage with, understand, and recommend the right thing to the right buyers at the right time.

Conversational sales will help your team:

  • Engage with buyers on their terms when their attention and intent is at its highest. Simply put, when buyers are on your website. It will help you grow pipeline by talking to potential buyers earlier in the sales cycle.
  • Understand buyers by asking questions, using signals, and other sources of data to know what they care about and why they should purchase your product. The data will give you insight into how to have contextual conversations with buyers.
  • Recommend what’s best for the buyer. Recommendations are a great way to educate the buyer, build trust, and help them buy the right thing. A recommendation could be a tip, an idea, a next step, a piece of content, or someone to connect with.

Conversational sales empowers you to chat with your buyers anywhere at any time. No matter if you’re at work, at the beach, or at the game. You’ll have better conversations and get more qualified meetings delivered directly to your calendar.

Philosophy of Conversational Selling

Today the buyer has reviewed a lot of information before they ever even talk to you. They have so many more options and their expectations have never been higher. So what does this mean for you? Your number one job is to be friendly and ask questions about what they’re looking to do.

You can no longer expect to move buyers through your own self-serving internal sales process. In fact, the only way to execute an effective sales process today is if it fits neatly into the buyer’s own discovery and information collection process.

Executing a sales process is what your job used to be. Now your job is to help people buy. You are their tour guide, recommender, and trusted advisor throughout the buying process.

You can craft even more personal conversations with buyers when you use firmographic, demographic, technographic, and behavioral data to understand buyer intent.

Buyers don’t care about your sales process. They care about how you can fulfill their needs and desires.

Before we dive in, let’s level-set to understand the principles of Conversational Marketing & Sales. It’s useful for us to think about this in terms of a framework: The old (or business-centric) approach vs. new (or customer-centric) approach.

Conversational marketing & sales always puts the buyer and customer first.

Principles of Conversational Marketing & Sales

Being more helpful and buyer-centric will pay you back over the long run. You’ll have a much higher chance that a buyer will become a customer if everyone at your business follows these principles.

In the past, live chat was typically only a tool for support teams. If you used live chat in sales you had to dedicate people to use it, it was filled with noise, and you likely didn’t have enough people to triage all the conversations. Salespeople hated it because they ended up fielding a lot of support type questions.

Now with conversational marketing and sales, chatbots start conversations and qualify buyers so your team can have the right conversation at the right time with the right buyer.

SDRs can continue their normal prospecting activities, but now they’ll get notified when a buyer wants to engage. This can happen when the buyer is on your website, when they open an email, when they click on a sales email sequence, or when they watch a video.

They might already be using real-time intent signals and with conversational sales they’ll get even more of these signals. For example, you probably get excited when you see a buyer forwarding that email you sent to a lot of people.

Or you’ve been chasing someone for a long time and they finally reply or finally pick up because the timing is right. This is what you’re going to experience every day with conversational sales.

You’ll be able to engage with a buyer on their terms because marketing has designed it so only the buyers that are ready and want to have a conversation will be able to connect with you.

Here are 7 ways to have buyer-centric sales conversations.

  1. Always understand what the buyer is trying to achieve (and why) before offering a solution. Do so by asking the buyer to clarify and elaborate.
  1. Be present and use active listening. You’re trying to understand where they are in their process. Use authentic stories to convey why they should care and take the next step.
  1. Show passion with your buyers. If you’re not fired up, they won’t be either.
  1. Confirm your buyer’s questions.
  1. Be transparent with your buyers on what you’re doing and any next steps.
  1. Share examples. A quick, “Hey would you like to see how (blank) is working for a business like yours?” goes a long way.
  1. Help the buyer buy. Keep them in mind and consider their position.

It’s easy to fall into the trap of thinking that buyers have a very structured and rational buying process, but any buying process is messy. The buyer wants what they want, when they want it. Never trash your competitors. Doing so makes you look insecure and doesn’t help your buyer make a decision. Help your buyer make a decision by clearly communicating your positioning and strengths/weaknesses compared to the competition.

The profile and skill set of a great salesperson continues to evolve. They must be empathetic, patient, and creative with have strong critical thinking abilities. In the next chapter we’ll discuss how the role of the sales development representative has changed and how to find hire great SDRs for your own team.

Hiring Sales Development Representatives

The success of your sales team starts with who you hire. The profile of what makes a great sales development representative (SDR) has evolved.

SDRs have to balance email, the phone, and LinkedIn to book meetings. And with the rise of  conversational marketing and sales, SDRs need to adopt best practices for using live chat to engage with buyers.

There’s good news though. Live chat will become your SDRs new favorite way to booking meetings. Many of the SDRs you’ll hire will already be using messaging tools.

Typically SDRs are hungry to learn how to be a great salespeople. They have intrinsic motivation and have been using messaging-based tools for many years. Things like WhatsApp, Facebook Messenger, and iMessage.

Many SDRs have ambitions to become account executives or manage a team of SDRs in the future. You should always be sharing why it’s so important to excel at  the job they’re responsible for today. The skills they’re learning will pay them back over the course of their entire sales careers.

If you’re selling an enterprise-grade product to very sophisticated buyers, you might consider hiring more experienced SDRs as opposed to those right out of college with limited to no prior experience.

Some pitfalls you should watch for are an SDR trying to get to the next step in their career too quickly, losing interest in what they’re doing, and / or not showing urgency. Try to hire SDRs who are passionate about sales and want to get really good at it by developing their own craft.

Good SDRs should be hungry to learn about your product, industry and business. Context switching is another important skill since SDRs switch between many different activities often.

Most importantly, you need to clearly set goals and share context behind why those goals are important.

Here are some traits you should check for in the interview process:

  • Patience
  • Outgoing nature
  • High standards
  • Highly organized
  • Strong writing ability
  • Ability to deal with obscurity
  • Self starter, intrinsically motivated
  • Good active listening skills
  • Desire to be the best
  • Ability to adjust to and learn new technology quickly

Focus on a candidate’s confidence before experience.

The most successful SDRs do three things:

  1. Focus on answering questions quickly and accurately
  2. Are great listeners and respond with good follow-up questions
  3. Have mastered the art of recommending the best next step for the buyer

As a hiring manager, make sure you’re also outlining the career progression steps for SDRs so candidates know there’s a path for them if they succeed.

How To Start Using Live Chat

Your team is most likely prospecting through a combination of emails, phone calls, and LinkedIn outreach. All three motions require you to wait for someone to respond. They’re passive activities that work (sometimes) but require patience and timing.

That’s where live chat comes in. It gives your team a real-time means of interacting and engaging with prospective buyers.

Introduce live chat to your team by having your best SDRs try it first. This isn’t about changing what they’re doing now. It’s about making what they’re already doing more effective and giving your team more at bats.

Ease your team into the transition. Emphasize that this is another tool in their arsenal, one purpose-built to help them reach their goal – booking more meetings for their account executives.

With live chat, you’re meeting the buyer where they are.

Now that you’ve introduced live chat to your SDR team, we’ll use the Conversational Framework  to explain how these SDRs can have productive live chat conversations


  • Introduce yourself or welcome site visitors back. Pay attention to your response time. How fast do you respond to the conversation? Best practice is to respond right away with a simple, “Hey, how are you?”
  • How quickly are your SDRs jumping in to the conversation? This should be less than 60 seconds.
  • How responsive are SDRs once they’re in the conversation? This is a live conversation so it should feel like one. Respond back within 30 seconds or less.
  • Pay close attention to how SDRs use information from past conversations to welcome visitors back or to ask more detailed follow-up questions.


  • The most important thing to do when jumping on a live chat is to answer the visitor’s questions directly. Don’t try to schedule a meeting or jump on a call. Answer their questions first. Then ask a follow-up question to see where they are in their buying process.
  • Pay close attention to the number of back and forth messages your SDRs have with buyers. A good conversation should feel like a friendly game of catch. Back and forth.
  • Train your SDRs on what qualifying questions they should ask. And the appropriate number of qualifying questions to ask in order to move the buyer to the next step.
  • Ensure your SDRs are aiming to uncover the deeper “why”.
  • SDRs should be trained to look for mentions of early stage words and questions. Questions like, “What is Drift?” for instance would show that that prospect is in the early stages of their buying journey.
  • SDRs should also be on the lookout for mentions that indicate the buyer is in the evaluation phase. Think of things like a competitor’s name or pricing questions.
  • Pro Tip: Track how many stages of the sales process an SDR gets through during a live chat conversation.


Make sure to always share some type of recommendation during any conversation with a site visitor. Most conversations will include multiple recommendations. The two most common types are sharing some type of content, ideas, or suggestions. And scheduling time to have a call with either the SDR or account executive.

Key things to look out for:

  • Did the person say they agree with your recommendation?
  • Did the person click on the link that was recommended?
  • Pieces of lead information collected (email, phone, name, company)

The conversations your team has with buyers should be useful. Recommendations are a simple and effective way to build trust and add value to a conversation. Make it easy for your SDRs to make recommendations by sharing a one pager of all the things they could recommend based on what the buyer is asking.

It’s obvious that your team can’t always be online to have live conversations. Don’t worry though. Even if your team is offline, you can still use a tool like Drift to book meetings:

  • When someone comes to your site
  • When target personas are live and showing intent

When buyers are on your site, you should always be there to help them have a conversation. Either right now or within the next day.

Here are the tools we recommend you use:

  • Drift Meetings: With Drift Meetings, you can target your best visitors and ABM accounts, welcome them with a personalized message from the right rep, and let them instantly schedule a meeting right from your website.
  • Drift Notifications: Answer site visitor questions in real-time, convert more leads, and start closing more deals.
  • Drift Video: Drift Video is built to make buying easy, allowing you to create and share videos that start conversations.

Analyzing Good and Bad Conversations

It’s important to consistently analyze the conversations your sales team is having with buyers. At the highest level you should look at what meetings and pipeline result from quality chats. The goal of analyzing conversations is to help each SDR get really good at helping people buy.

So what are some good conversational cues to look out for and bad ones to avoid?


  • Responded in under 5 minutes.
  • Had a back and forth cadence. If you listened to a rep’s call and they were talking the whole time you’d be worried right? Same goes for chat conversations. It should be a back and forth.
  • They personalize the experience for the visitor. If the SDR knows who the visitor is, or at the least, what company they’re with, the SDR  can make them feel more comfortable. This also applies to referencing recent chat history. For example, if the SDR  can see on their record that they had a few chats recently and the says, “Hey welcome back. Did you still have questions about that feature you were asking about before?” That’s an amazing experience.
  • How far and how quickly the SDR is able to move the buyer forward in the qualification process. If they are a good fit, but not ready for a call that’s okay, but the SDR should have content to direct the visitor  to so they can learn more. Bonus here, make sure there’s a sequence established for follow up later on.


  • The SDR took forever to respond or asked to get on the phone before the visitor even responded. They should be engaging the visitor and understanding where they are in the buyer journey before they recommend what to do next.
  • The SDR is treating sales chat like support. If SDRs just answer questions and don’t ask for qualifying information nor ask to take the next step, they won’t hit their numbers. Managers can spot this when SDRs respond to a question and don’t ask any kind of follow up questions about pain points or use case.
  • Not being real. This happens when someone asks a technical question or a pricing question and the rep just tries to force the person to get on the phone. It’s absolutely okay if the SDR doesn’t know an answer. But they should admit that up front and then say, “Hey the best person to answer that for you is X. Can I connect you with them?”

Bad behavior frequently pops up around the end of the month when reps are either already at their quota and coasting or are so far away from their goal they just don’t care. Remember it’s all about building around your buyer’s experience. If the SDR delivers a great experience, sales results will follow. Don’t let your reps’ own incentives get in the way.

Pro Tip

  • Share great conversations in Slack to praise your team, especially when one of your top reps really handles a tough objection or helps win a meeting / deal against a competitor. It will fire up your team and show everyone what good looks like. Have a regular check in with your reps and marketing to keep feedback flowing. Almost all of the issues you might hear from reps about notifications or quality of chats are often easily solved with a quick update of your chatbot logic and targeting. Keeping that feedback flowing makes everyone’s lives easier and little quick wins compound over time.

Sales Manager Best Practices

It’s important to coach your SDRs on how to better use and balance live chat during their day. We strongly recommend that you coach your sales team so they’re playing the long game vs. the short game with a buyer. Make sure they’re not over indexing on just hitting demo and meetings numbers. SDRs should focus on helping the buyer get to the next step.

Pro Tip: SDRs using live chat should mirror what a great face-to-face sales conversation feels like.

Make sure SDRs understand and get better at using the engage, understand, and recommend framework. Make sure they’re introducing some type of small talk into each conversation. Even just a couple of lines go a long way.

Your SDRs now have multiple tools at their disposal to have conversations and book meetings. Make sure they’re clear on how they should prioritize their activities.

  1. Always prioritize real-time conversations however and wherever they happen
  2. Start a conversation with the help of marketing materials

As the SDR manager, you must be closely aligned to your demand gen marketer. You should participate in quarterly and monthly planning and strategize together regularly so your SDRs are in the best position to start conversations.

How Should SDRs and AEs Work Together

There’s no good in just booking meetings if they don’t turn into real customers. Pay attention to how your SDRs introduce buyers to account executives. Consider breaking up AE vs. SDR targeting by company size, industry, and / or revenue. Both parties should end the week with a review. Review why an AE or SDR did / did not book the agreed upon number of meetings. Focus on what worked and what didn’t.

SDRs should help build rapport for the AE by connecting the dots – the relationship should be obvious on the first call.

SDRs should stay curious about deal progress and make sure they know who the key stakeholders are in the unfortunate case that a champion leaves.

SDRs should nurture the account throughout the first call until the SDR and AE agree how to move the deal forward. It’s all about turning the pipeline into revenue.

Here are the steps that work best to align SDRs and AEs. The following should serve as a guide to help you create strong relationships between SDRs and AEs:

  • Meet on a weekly basis
  • Identify target accounts (account-based selling)
  • Work together to identify the accounts to focus on for the coming week
  • Work on crafting messaging together using marketing activities and assets like events, new content, webinars and product announcements. This is your fuel.
  • Agree at what point an opportunity gets created
  • Agree to who is responsible for logging what in Salesforce or your system of record
  • Determine how much qualification should or needs to happen
  • Consider bringing SDRs to onsites

Ideally the SDR and AE use the same qualification steps / methodology. The only difference is the level of detail. The AE should guide the SDR to uncover 1 to 3 key qualification steps. For instance, and this is simplified, but they might include:

  1. Does the customer have a pain?
  2. Is a solution worth exploring?
  3. Will the customer agree to taking steps to exploring your solution?

Here’s why having your SDRs and AEs work together is so important. Drift’s Director of Account Management, Sam Jones, has recently focused on “no show rates.” It’s soul destroying for both the SDR and AE when an account agrees to a meeting but never shows. The more steps, gates and complexity you add to aligning calendars once the customer agrees to a meeting the greater the risk of a NO SHOW.

Never forget that your team’s job is to help people buy. Conversational sales empowers your team to chat with buyers anywhere at any time.

Want to learn more about how Drift can help your team schedule more meetings? Book a time to chat with one of our conversational sales experts here.

10X Your Sales Team's Productivity Now

The ultimate guide to help you engage more buyers and book more meetings with conversational sales.