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The Guide to Conversational Email

Are your marketing and sales teams struggling to make an impact with your current email marketing program?

This guide provides the ‘why’ and ‘how’ for using conversational email marketing to modernize your communications strategy.

The Guide to Conversational Email


Chapter 1


Chapter 2

What Is Conversational Email?

Chapter 3

What Conversational Email Looks Like

Chapter 4

Conversational Email Capabilities & Use Cases

Chapter 5

5 Biggest Challenges Conversational Email Tools Can Solve

Chapter 6

Conversational Email Improves B2B Sales Rates

Chapter 6

Conversational Email Improves B2B Sales Rates

Chapter 8

3 Ways Sales Reps Can Use Conversational AI to Generate More Authentic Emails

Chapter 9


Table of Contents

Chapter 1


How hard is it to stand out in email marketing?

  • In 2020, 306.4 billion emails were sent and received each day
  • Most office workers probably receive more than 130 emails a day
  • Generally, about one in five of those emails are opened … and of those emails, less than 3% actually generate a click-through

Where have marketers gone wrong?

Too many marketers forget to put the customer at the heart of their marketing. They forget that leads are actual human beings. Humans with problems, humans searching for a solution, humans trying to get things done.

It’s time to build stronger trust and relationships with people.

It’s time for conversational marketing — and especially for conversational email.

Chapter 2

What Is Conversational Email?

Conversational marketing is a customer-oriented marketing approach that engages customers in highly scalable, “dialogue-driven, personalized experiences at a one-to-one level,” writes IBM, that enable “brands to listen and gain unique customer insights while also providing value to the user.”

Sounds great, right? But who has the time to start a conversation with every single lead in real-time?

You do — using conversational email. Conversational email is initiated by artificial intelligence assistants, customized by your team for your prospects. With this breakthrough application of AI, your revenue team can now:

  • Use AI to generate personalized email content at scale
  • Utilize AI to automate the process of sending emails
  • Allow AI to work as a virtual assistant, aka an AI assistant

What are AI Assistants?

AI assistants are automation tools that help marketing and sales teams automate tasks, including:

  • Qualifying leads and following up
  • Routing hot leads to the right sales reps
  • Scheduling meetings
  • Collecting data
  • Piping data between applications

Handing these rote tasks to AI frees your revenue team to focus on complex, engaging parts of the process, like closing deals.

Chapter 3

What Conversational Email Looks Like

You’ll get a lot of info and best practices about conversational email in this document. But before we plunge into that stuff, it helps to understand the concepts behind building and implementing conversational email programs.

Conversational email marketing is easy to implement. It fits right into your tech stack and integrates seamlessly with your favorite marketing tools.

Below is an illustration that presents how conversation flows can be crafted and customized within a conversational email platform. The story flows clockwise, with the platform’s configurable AI assistant acting on your behalf to automatically:

  • Email prospects
  • Receive, analyze, and classify replies from leads
  • Activate next steps such as sending a meeting invite, sending relevant content, and more

You can also easily add scenarios to specific conversation flows. This means you can add new email actions activated by criteria you define. In the illustration below, the platform’s AI is configured to identify when prospects request additional information and automatically reply with the most relevant asset:

From an under-the-hood tech stack perspective, the illustration below shows how conversational email solutions can work with existing marketing automation systems to engage accelerate MQLs, continually re-engage accounts, and automatically pass interested buyers to human sales reps:

Humans Matter, More Than Ever

These robust AI decision-making capabilities eliminate tons of manual effort for marketers and sales teams.

But it’s important to know that AI assistants are not a replacement for human SDRs and sales reps. They’re not intended to replace any of your existing ops people, processes, or marketing automation tools (like HubSpot, Marketo, Pardot, etc.), either.

Conversational email systems exist to work alongside your human and technology resources, and radically enhance their productivity and impact on pipeline.

What Needs AI Automation?

Here are ways to identify which tasks can and should be automated:

  • It’s a repetitive or frequent task your team does
  • It involves moving data from one application to another (CRM to Marketing Automation to Sales Reps Emails)
  • It’s a boring task that requires little thinking, or takes away from higher value tasks.

Chapter 4

Conversational Email Capabilities & Use Cases

Your hottest leads need the direct attention of your sales team. But that leaves a lot of unattended potential, such as:

  • Prospects that might fit into your Ideal Customer Profile but haven’t shown interest
  • Companies that tentatively raised a hand but might not be ready to buy, or
  • Folks who were previously engaged but dropped off along the way

All of those leads represent potential pipeline, but who has the time — or the headcount — to reach out to all of them personally?

The need to connect with lukewarm and cold leads is the perfect place to pull out your conversational email playbook. Using personalized automated conversations like the kind seen above, you can offer these potential leads:

  • Marketing content that is highly relevant to their interests
  • Invitations to events they’re likely to attend
  • Reminders of your company’s benefits that matter to them

When the prospect is warm and responds for a one-on-one connection with your team, your AI assistant will loop in a human sales rep to take over.

Conversational email marketing’s uses are limitless, but let’s go through several example scenarios that can offer your team big returns.

Conversational Email & ‘Collaborative Intelligence’

Most knowledge workers spend less than 50% of their time doing what they are hired for. Instead, they’re conducting research, collecting data, arranging meetings, and performing repetitive and mundane tasks.

Why not let people focus on higher-value tasks requiring judgment, experience, and human empathy?

Collaborative intelligence means supporting human work with AI tools, using technology to manage and streamline workflows. AI is good at certain things, such as performing repetitive, multithreaded work, analyzing huge bodies of data, and handling routine tasks.

Delegating those duties to an AI tool frees humans to do what they do best: resolving ambiguous information, exercising judgment in complex situations, and building relationships.

Collaborative intelligence combines the best of AI with the best of people — working together to achieve your organization’s goals.

Example Scenario 1: For New Leads

Website Inbounds

AI-powered conversational email can effortlessly respond to every inbound lead from your website — and at a speed that even the most efficient human can’t rival.

An AI assistant can immediately start the conversation and offer content that syncs seamlessly with the prospect’s interests — and when they’re ready for a meeting, the assistant can cc: a sales rep to take over.

All the warming, none of the work.

Why Reaction Time Is So Important 

Consider this recent research regarding speed-to-lead response times:

  • Nearly 8 in 10 customers buy from the company that responds to their inquiry first
  • You’re 7x more likely to qualify a lead when you reach out within an hour as opposed to just one hour later
  • Only 7% of companies respond to leads within five minutes, while 55% respond in five or more days
  • If you make contact within five minutes, you are 100x more likely to connect with a prospect than if one hour has elapsed
  • You’re 21x more likely to convert a lead into an opportunity when responding in five minutes or less

Leads Below the MQL Threshold

Marketers often don’t know what to do with Pre-MQLs (leads which are stuck below the MQL threshold). It’s usually not worth your sales team’s time to engage these leads, but it’s not worth outright abandoning them, either.

Your AI assistant can attempt to dislodge these leads from their pre-MQL status by using a content offer via conversational email to optimize engagement.

Low-Scoring Leads

Low-scoring leads might have recently engaged with your content, but aren’t yet MQL-ready. You can still move those leads through the funnel by having an AI assistant reach out through conversational email.

Content Offers

The warm touch of conversational email is a fantastic opportunity to move prospects and leads through the sales funnel by sharing your marketing content.

Your AI assistant can offer — and deliver — ebooks, white papers, playbooks, guides, or any other great content you’ve got, to increase the prospect’s knowledge. (We’ll talk more about conversational email and content marketing in a few paragraphs.)

Accelerate MQLs Into SQLs

New MQLs can take a a lot of nurturing. You want to prevent genuine MQLs from slipping through the cracks, but don’t want to waste time pursuing unresponsive leads.

Conversational email takes the revenue team out of the equation but still ensures all new MQLs are worked adequately.

Example Scenario 2: For Engaging Existing Leads

Re-engage Dormant MQLs

Your CRM is home to lots of open MQLs that never closed. Why let that previous work go to waste? Conversational emails can revive interest from old leads and convert them to sales opportunities.

For instance, you could re-spark interest by customizing emails for your AI with a new product offering.

Recycled MQLs with No Sales Activity

Also hiding in your CRM are high-scoring inbound leads that have not responded to, or have not yet connected with, your inside sales team. These leads still have potential — especially if you can offload the task of engagement from a rep to an AI assistant.

Conversational email can accelerate an open prospect’s buying timeframe by marketing the benefit of acting sooner rather than later.

Lapsed Leads

Sometimes the revenue team drops the ball, but all is not lost. Let’s say high-intent leads from a webinar were handed over to the sales team, but weren’t touched within 72 hours.

A conversational email designed to engage and convert those leads can “reset” the opportunity by warming people back up before handing them back to your sales team. Just like that, the ball’s back in your court.

Cold Leads

Cold leads in your CRM can be re-touched with a personal approach by AI, gauging their current level of interest. If they are ready for more, AI will loop in a sales rep to take over.

Example Scenario 3: For Events and Webinars

Ninety-eight percent of exhibitors collect sales leads at trade shows. However, less than 70% have any formalized follow-up plan or process in place for those leads.

That’s a massive waste of leads. Following up should be a top priority if you want to close post-event sales. According to Marketo, the first vendor to email leads after events gets a 3x higher click-to-open rate than the third vendor.


You can drive registrations to your webinars or virtual events by issuing personalized invitations via conversational email. This is a low-pressure, high-value way to initiate conversations with unresponsive leads.

Your AI assistant will reach out to your leads (with emails you’ve crafted) and automatically register them for the event when a lead replies, “I’m interested.”


Events and webinars can generate great leads — too many, sometimes. We all know timing in post-event follow-up is key, but sales teams can’t always contact every attendee personally.

And just because someone attended a webinar doesn’t make them an MQL. But given that they’ve raised their hand by attending, the odds of being able to make a big impact with immediate outreach greatly improve.

Conversational email meets the time-sensitive needs of follow-up without unreasonable demands on your sales team. A post-event content offer from your AI assistant supports the event’s goals and is an easy way to increase the knowledge and interest of even low-intent leads.

Example Scenario 4: For Free-Trial Conversions

Many SaaS businesses use free trials to attract leads. But many of those leads remain undecided or give no indication of their interest. Without follow-up, these leads turn cold and end up forgotten in CRMs.

AI assistants can automatically connect with free trial users via conversational email and ask if they are interested in learning more about the product. When a lead is ready, the AI sales assistant will route the lead to the sales team.

If your organization has cold free trial users, your AI assistant can reconnect with them via conversational marketing too, offering news on updates and changes to the product, or value-adds such as custom demos.

Example Scenario 5: For Using Content to Get Qualified Sales Meetings

Content marketing is great for attracting leads, especially when you have a great content offer like a well-researched report or solid case studies. But not every lead who downloads a content offer is a potential customer. Some want the information for their own research purposes, while others are tire-kickers who never buy.

Unfortunately, many B2B tech companies don’t have an effective way of identifying genuine potential buyers that come via content offers.

AI assistants can follow up with anyone who downloads content to start a conversation. They can offer — and deliver — additional complementary resources and answer basic questions to evaluate interest.

By the time the lead is ready to request a meeting, the assistant will already have valuable information to help sales evaluate the lead and offer the right information at the right time.

Chapter 5

5 Biggest Challenges Conversational Email Tools Can Solve

Martech can feel miraculous. It offers revenue teams the ability to deliver effective campaigns at a scale they never would be able to achieve manually.

But it can also come with its own onerous set of management tasks that take time away from other, more valuable work.

Here are five ways AI-powered conversation email tools can boost your revenue teams’ productivity:

1. Dynamic Segmentation & List Management

Segmented email campaigns register 50% higher CTRs than untargeted campaigns. However, manually segmenting your email list and keeping track of customer interactions is a time-consuming and tedious task that can quickly become unmanageable as your list size grows.

AI-powered email marketing automation tools eliminate this challenge by automatically segmenting your list based on customer behavior, interests, and demographics. AI can also help you keep track of customer interactions and automatically update your segments in real time.

Since AI-powered dynamic segmentation leverages customer data, it’s also more accurate than manual segmentation, which often relies on hunches and guesswork.

2. Content Creation & Personalization

Addressing your audience by name, referencing their specific pain points, and tailoring your content to their interests increases open rates and CTRs by up to 35%, resulting in deeper engagement and more sales opportunities.

But content personalization doesn’t mean inserting %FIRST NAME% in an email template. To drive the best results, your emails should be tailored to your prospect’s:

  • Stage in the buying process
  • Recent online research, and
  • Interactions with your website and marketing campaigns

Delivering this kind of personalization at scale is nearly impossible without the help of AI. Your AI assistant can analyze the latest data about each customer and deliver content that is tailored to their specific needs.

3. Email Delivery & Subject Line Optimization

The best email content in the world is meaningless if the recipient never opens the message.

AI can look at the interaction habits of individual contacts and determine when each contact is most likely to open and respond to your email.

And your AI assistant can craft subject lines for each contact, and learn which messages they read. It then tracks engagement to improve and optimize over time.

4. Campaign Monitoring & Insights

AI-powered conversational email platforms can provide valuable analytics to marketing and sales teams, helping you identify trends and patterns in customer behavior.

For marketers, these insights help you quickly A/B test new campaign tactics to drive pipeline growth.

For sales representatives, AI can deliver granular insights into which accounts are becoming more engaged with content, and which topics have their interest. Once an account qualifies for outreach, you’ll be armed with great talking points.

5. Lead Nurturing & Sales Cycle Shortening

B2B sales cycles can be really long. When customers are investing in a complex service or product for their business, they do a lot of research. Your emails should enable as much of this research as possible and make it easy for customers to connect with a sales rep when they are ready.

By providing specific content tailored to individual customers’ needs, AI can help speed up the research process. And better-informed prospects become closed deals much faster.

Chapter 6

Conversational Email Improves B2B Sales Rates

Marketing in the B2B sector often focuses on lead generation. But here’s a challenge most sellers face on the daily:

You must keep your pipeline full of prospects — but in the process, you risk pulling attention away from other critical metrics, like conversion rates.

Without the right tools, those tasks can become a quagmire of manual activities that make it impossible to track every lead and prioritize the ones most likely to convert.

An AI-powered conversational email assistant can help your sales team with a variety of functions designed to save time and improve engagement. Here’s how.

Quickly Respond to B2B Leads

B2B buyers are accustomed to getting what they want when they want it. As we mentioned earlier, when revenue teams take too long to respond to buyer engagement (such as a Contact Us inbound), those buyers bolt in favor of other solutions.

When a potential customer makes contact, your AI assistant can trigger an instant response in the form of a personalized email, informed by captured data. You can also set up priority-based alerts to make further contact with the prospects who’re most likely to purchase.

Prequalify Leads for You

Prequalification is necessary, but it’s often time-consuming and forces salespeople to disrupt their productive workflows. AI-powered email assistants can take manual tasks out of your hands with an automatic reply to potential customers. Your AI email assistant will:

  • Reply to potential customers with a series of predetermined questions
  • Use the customer’s answers to provide additional resources or book a meeting so you can have a conversation
  • Engage and qualify your leads at scale to identify genuine buyers and route them to sales

Write Your Own Emails Faster

Three out of four B2B marketers agree that personalization enhances the engagement rate, but we all know that personalizing content at scale is tricky. Response templates are available for practically every situation, but they usually sound generic … and buyers can easily spot a too-broad “canned” response.

AI assistants can tap into data you’ve already collected about the customer, enabling the software to near-instantly craft emails that speak to the person and their unique concerns, not just the opportunity you’re trying to offer.

AI-powered tools can also use algorithms to:

  • Understand and emulate your writing style
  • Automatically correct unprofessional grammar
  • Improve style

These tools can work with your writing style to speed up repetitive text like greetings and allow you to concentrate on informative, communicative writing.

Proactive Outreach

Even with a robust CRM, it’s easy to let leads fall through the cracks.

A contact in your CRM who only gets one or two touches and fails to respond may never be worked again until they’re moved into a “dead” or “inactive” status. This type of delayed contact could be too late to convert hesitant leads.

The smartest conversational email tools:

  • Tap into your CRM and seek contacts that haven’t received much communication
  • Initiate nurture campaigns to reactivate those opportunities
  • Use machine learning to identify which prospects are most likely to convert based on the customer’s behavior

A similar process enables the AI assistant to engage contacts that failed to respond to earlier contact. This additional engagement can provide additional resources or lead to an appointment for more detailed communication with a sales rep.

When you automate communication processes that take place early in the sales funnel, you can effectively — and practically effortlessly — address your prospects’ pain points and concentrate on buyers ready to convert.

Chapter 7

How Conversational Email Resurrects Neglected Leads

Neglected leads are leads sitting in your database with no sales activity. No matter where the leads come from — webinars, events, free trials, recycled MQLs, ebook downloads, old closed-lost opportunities due to “no decision,” etc. — you did spend time and money acquiring them.

Neglected leads are a silent, massive problem for demand generation and marketing operations teams.

Understanding the Root Cause of Neglected Leads

Most companies have a ton of revenue potential locked up in neglected leads, and here’s why: reps hate working them.

It’s not because salespeople are lazy. It’s because working on low-propensity leads is not a good use of their selling time.

If you want to fix the issue once and for all, you need to ensure that lead measurement starts when a buyer is ready to have a conversation with your sales team. Fortunately, this is another place AI-powered conversational tools can save the day.

Traditional vs. Automated Lead Conversion

Traditional lead conversion systems use lead scoring and manual lead assignment to prompt humans to follow up.

Automated lead conversion systems help marketing teams engage, qualify, and follow up contextually with leads, with the single-minded goal of surfacing those that are ready for a conversation to pass to the sales team. The best AI assistants, which power conversational email systems, can do this work for you.

Some systems also take care of the back end: routing information to the right sales reps, scheduling meetings, collecting conversational data, and piping data between applications.

And here’s the best part — instead of a traditional system where marketers and sales reps are doing that work manually, automated lead conversion systems can make all of those tasks happen automatically in the background.

Why You Should Use Automated Lead Conversion Systems

There are three main reasons every marketing and demand generation team should consider implementing an AI-powered conversational email solution that can automatically convert leads:

  1. ROI on marketing budget
  2. Closing the loop on marketing attribution
  3. Control

Let’s take a closer look at each.

1. ROI on Marketing Budget

Marketing budgets are tight right now. Every single dollar is being scrutinized for ROI.

Automated lead conversion systems ensure you get maximum yield from your marketing programs by allowing you to maintain close to 100% coverage on neglected leads.

2. Closing the Loop on Marketing Attribution

When the coverage of MQLs being worked on by sales is so uneven, how can marketers know which channels definitively have higher ROI than others?

For instance: If a trade-show event fails at generating pipeline and revenue, was it (a) because your marketing team did a bad job, (b) trade shows don’t work for your business, or (c) sales didn’t have time to work the trade-show leads?

This uncertainty skews your data, and makes it hard to understand which channels to focus on and how to optimize your acquisition cost.

3. Control

Automated lead conversion systems put marketing back in control over the leads they generate. With these systems in place, marketing can tell sales, “You can just focus on your sales meetings and having lots of conversations. We’ll do the rest.”

Chapter 8

3 Ways Sales Reps Can Use Conversational AI to Generate More Authentic Emails

B2B email marketing is a delicate balance of effort, time, and results:

  • The best results come from meticulously personalizing each email’s content and arrival time for the greatest potential impact.
  • But the best use of time is “blasting” at scale to reach everyone on your email list. These generic emails ensure that your message gets out to a wide audience, but they often feel more like an “extended auto warranty” robocall than legitimate human outreach.

By smartly leveraging AI to craft your emails, it’s possible to grasp the best-possible benefits of both worlds.

Here are three ways AI-powered conversational email can, paradoxically, help you write less robotic emails.

1. Know Your Leads — Programmatically

Traditional email automation has fairly rudimentary personalization capabilities; it’s often used to insert the name, company, and perhaps role/business function into emails, and little else.

This approach simply isn’t specific or resonant enough. To reach buyers in ways that authentically speak to their concerns, you need tools that can read a CRM and generate a comprehensive understanding of each lead.

AI-enhanced conversational email can recognize a lead’s industry, niche, preferences, and behavior patterns through already archived data and create personalized email campaigns that take all known factors into account, along with a few pre-established strategies created by your revenue team.

This enables your B2B AI to predict the types of content, products, and subject lines that would be the most interesting to each individual lead. Better still, your business can do all this without requiring time-consuming analysis from a human sales rep.

2. Personalized Subject Lines Improve Open Rates

We all know that subject lines inform a buyer’s near-instant decision to read or delete an email. And we also know that most are deleted without a second thought.

But personalized subject lines, which are honed to inspire interest and trust in targeted leads, are far more effective than generic subject lines — even well-written ones.

According to an Oberlo study, personalized email subject lines generate an average of 50% higher open rates. But who has time to personalize every email subject line without starting to feel and sound robotic themselves? AI does.

AI-powered subject line personalization analyzes industry and keyword interests to design engaging subject lines for every lead on the email list. The subject lines won’t be the same and won’t necessarily even follow the same format.

3. Personalized Content Increases Interest and Engagement

The real kicker, however, is personalized content in each outreach email.

Your customers are not cookie-cutter copies of each other. They may work in different industries, vary by size, and have extremely different needs based on their job role. Each member of a buying team has their own concerns and goals.

This means what a buyer might want to see often differs wildly from account to account … and even within each account.

When buyers open your emails, they should find content that:

  • Relates to them
  • Is relevant to their current role
  • Offers solutions to timely challenges

Your conversational email AI assistant can select the right mix of content and topics to keep leads engaged and show that your brand is attentive to their unique business concerns.

Chapter 9


Collaborative intelligence — combining the best of AI with people smarts — can rocket your revenue team upward toward your goals.

It’s really that easy and that good. Conversational email marketing, powered by AI, delivers results:

  • Warming cold leads
  • Nurturing low-scoring leads
  • Accelerating pipeline
  • Rescuing your revenue team from rote tasks
  • Customizing and personalizing messaging at scale
  • Delivering content and value to leads
  • Making marketing efforts pay off in genuine SQLs
  • Coordinating information and data across your martech stack
  • Managing sales hand-off

Fifty-four percent of executives are already experiencing increased productivity, cost reduction, efficiency, and revenue growth using AI. Offering a better customer experience will be crucial to success in the future of email marketing.

It’s time to join them, using AI-powered conversational marketing assistants to move your business forward.

The 6sense Team

The 6sense Team