How to make the most of chatbots for enterprise selling

See how chatbots can fit into your enterprise workflow with this guide. They personalize content, filter out traffic, and can alert you when top accounts hit your site.

Shelly Weaver
Shelly Weaver
December 8, 2022
min read
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Commercial reps can dial all day and if they upset a prospect, it’s unfortunate but unimportant. We are not so lucky. With just a handful of accounts and a more complex cycle, we can’t afford to pester. 

Enterprise reps tend to care more about quality than quantity, and the buyer’s experience above all else. That’s why it’s so important that you and your ADRs are on top of things, so when prospects visit your website, you’re ready. And if none of you are available to chat, the chatbot has your back.

In this guide, we won’t say that chatbots and conversational marketing are everything. But if you want to be an insight seller with an edge over the competition, they can be close to indispensable.  

What is an enterprise chatbot?

Plain and simple, enterprise chatbots are any conversational interface that allows website visitors to interact with a corporate website, tweaked to work with the organizational flow of an enterprise business. 

These can be chatbots that answer FAQs, ask qualifying questions, or route visitors to the appropriate team to answer questions. But most importantly, these chatbots can help ensure that VIP buyers get to a real human as quickly as possible, filtering out irrelevant traffic and removing any friction from the buying process.

Where do chatbots fit into my enterprise sales flow? 

For a long time, buyers' journeys have been expanding. Three-stage funnels have lengthened to a sprawling six. Forms have grown longer. Every business appears to be its own print shop and media company. If you think your buyer doesn’t notice this increased complexity, think again. 

The average buying committee has 6-10 individuals, each relying on 4-5 sources of information, trying to make sense of a world where every vendor is trying to creatively position itself. Each vendor’s increased internal sophistication has led to increased external complications. For as Conway’s Law reminds us, your external communications reflect your internal ones. If it’s complex for your team, imagine your buyer.

These dynamics make it increasingly difficult for customers to make purchases. In fact, more than three-quarters of the customers surveyed described their purchase as very complex or difficult.”


Gartner recommends looking at that challenge in terms of the “jobs” those buyers have to do, and finding ways to simplify them. For example:

  • How can you help them identify their problem faster? 
  • How can you help them understand the solutions available? 
  • How can you help them build requirements? 
  • How can you help them select you?
  • How can you help them create an internal consensus that you are the one?

The answer to most of these questions isn’t to do more. It’s to do less and create less. And that’s one area where enterprise chatbots for sales can help. 

Benefits of an Enterprise Chatbot

  • Personalize content to visitors: Your marketing team can program the chatbot to surface specific content to each target account. And rather than relying on prospects to scour your resources section, that chatbot persists across every relevant page, offering that uniquely relevant resource. 
  • Filter out irrelevant traffic: If you’re using a conversational telling tool, it can use the visitor’s behavior, IP, and other data to identify their account, and decide to present a chatbot or route them to the salesperson. This means you’ll only get alerts for accounts on your target list. All others will interact with the chatbot. 
  • Give top accounts a VIP experience: If the enterprise chatbot captures information that reveals a visitor to be a target account, it can notify you and your ADRs, and one of you can join the chat. That instant connection helps you answer questions right when prospects want to speak, rather than playing phone tag. If it’s easier, you can also initiate a video chat from the browser and talk then and there. The result: A VIP experience for your very important buyers.
  • Connect the dots across multiple researchers: If people across multiple of the account’s divisions are conducting research, a conversational tool with a chatbot will notice. Chatbots don’t sleep. They’re functionally around-the-sun support. And a conversational selling tool can aggregate that data into account scores that tell you when key accounts are surging. You can view a dashboard showing the relative “hotness” and research history for all accounts, which tells your ADRs which to focus on.
  • Upsell existing accounts: Because enterprise chatbots are ever-present and ever-qualifying, they can help you source extra upsell and cross-sell deals across divisions. Wherever someone from that account engages, no matter where in the world, either that chatbot or your ADRs can respond. 
  • Tackle key objections, even during buying committee meetings: If someone has a question about price, and visits that page during a meeting, you and your ADRs can be on that pricing page to answer their questions. That goes a long way to helping your buyers overcome internal objections and build consensus. 

And perhaps more than anything, chatbots for sales help you dig in for a long, drawn-out evaluation. Wherever your enterprise accounts appear, you’ll either be offering personalized responses via a chatbot, or hopping into the chat—even from mobile

How to launch and begin selling with an enterprise chatbot

If you’re using a conversational sales platform that includes a chatbot feature, there’s probably less to set up than you think. The actual installation of the chat tool is fairly low lift—just a piece of javascript that engineers can add to the site, no different than Google Analytics.

The next piece—the Salseforce integration—will vary depending on the provider. But most should have native integrations, especially if they’re built on the Force.com platform. (The stronger that Salesforce integration, the better it’ll be able to match your custom routing rules. It’s an argument for more expensive solutions, because it means you’re more likely to get every meeting with a matching account.) Very likely, that integration is something your CRM, business systems, or RevOps team can accomplish with Salesforce credentials alone.

Real-time lead routing is vital

Conversational platforms integrate with Salesforce using API calls, and not all API-based systems are coded the same. If the one you’ve selected one that sends updates in batches, you probably won’t get notified your buyer is chatting until the session is over. When evaluating solutions, be sure to ask about this—and test the vendor’s chat yourself.

Writing an enterprise chatbot script

Don’t surrender full control of the script writing to your marketing team. While they’ll probably do a serviceable first pass, they’re often further away from the buyer than you are, especially if you’re working just a handful of named accounts. Ask to review the scripts and consider writing your own.

When writing a chatbot script, write it with the intent to engage and qualify. If the visitor never clicks to chat, nothing else that follows matters, so pour most of your time into that opening question. (It’s a lot like an email subject line in that way.) Bonus points if you can automatically insert the name of the account, or some piece of information that conveys that you know who they are. (Without using personally identifiable information.)

Examples of good questions:

  • Hey [Company]. Can I ask you about [feature or pain point]?
  • Hi [Company]. Can I ask a question?
  • Hi [Company]. Let’s talk [feature or pain point]?

Examples of bad questions: 

  • Hi there partner. Can I tell you a secret? 
  • Can I tell you about our business solutions? 
  • Hi [First name]. Care to chat? 

From there, think about qualifying. Capture names, email addresses, business units, geographies, or whatever else is important for you to understand whether this person is worth engaging with. These questions should be binary and err on the side of sending them to a chatbot. For example, unless someone only qualifies on two out of three pieces of necessary information, they don’t meet the threshold, and the chatbot will send them a white paper.

If the chatbot offers up content, be sure that it’s relevant to that account. This is one big advantage of chatbots: Unlike website personalization, it’s a simple matter to surface up your top 1-3 assets for each account to see, in one place, which follows them around pages you’ve selected it to appear. Like an ad, it may take them multiple views or engagements to click and read, but the chatbot will helpfully persist.

Here are a few additional tips for writing chatbot scripts:

  1. Omit needless words.
  2. Explain things as you would to a friend.
  3. Don’t use phrases you wouldn’t use in-person
  4. Limit your punctuation—if in doubt, delete those exclamation points.
  5. Aim to be helpful above all else.

Measuring enterprise chatbot success

How will you know if your chatbot is contributing to this year’s pipeline? Measure it the same way you would any meeting-driving member of your team: By how many meetings it helps drive. Capture data from a “control period” before you had the chatbot, possibly with help from your RevOps or marketing operations team, then compare:

  • How many more meetings did you book compared to the control period? (E.g. Compared to this quarter last year)
  • How many additional assets did individuals at target accounts download versus the control period?
  • How many total requests to chat plus form fills compared to just form fills from the control period?

Other brand-building benefits to enterprise chatbots

The more qualified the buyer, the more likely they are to want to talk to a human. That’s according to research by Gartner, which found that by segmenting whether a deal was ultimately a high-quality one or not, they were able to tease out varying behaviors between the serious and the not-so-serious. So-called “high quality deals” are also more interested in detailed product content. 

Despite this, the marketing and sales automation trend over the last decade has been to remove the direct line between buyers and salespeople. It’s been about more AI-driven recommendations, more automated email flows, and of course, more conversational chatbots. But this is where your chatbot can be a differentiator. 

Most chatbots can only escalate conversations to whatever human is currently monitoring the chat tool. That means if an enterprise buyer who’d rather get detailed product information from a human arrives on the site, they’re probably going to talk to a somewhat junior SDR who’s mostly interested in booking a meeting. But with a conversational sales tool like Qualified? That conversation goes straight to you or one of your ADRs.

Gartner: High-quality deals prefer to talk to people. 

Only Qualified has the depth of Salesforce-native integration to query your CRM routing rules in real time and alert you before the chat bubble loads. Qualified will even tell you when that prospect is on the site, even if they tap the chat. 

And when you and your team are consistently the easiest salespeople to reach—whether that’s with someone you’ve spoken to before or an influencer in an entirely different business unit—that’s a big advantage. It builds your brand. 

In that way, the most human way to interface with clients is, counterintuitively, a chatbot. 

Enterprise sales chatbots for the win

Commercial sales reps can get away with lots of things enterprise reps and their ADRs can’t. If your prospects want to talk to a smart human quickly, and you can’t waste any interactions, chatbots are a great way to go. They filter out irrelevant traffic, give those target accounts a VIP experience, and help you connect the dots.

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