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Conversational Selling and Conversational Marketing

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By Dani Apgar and Tony Medrano

Conversational Selling and Conversational Marketing are the latest and greatest tools for connecting with and having conversations with customers. If they’re not in your tool shed, they should be. We’re going to start by reviewing what makes each strategy unique. We’ll then describe successful implementations of each strategy to help you leverage them for your business.

Conversational selling often occurs in a B2C context and means replacing the traditional e-commerce experience with a one-on-one conversation that is as casual and intimate as an interaction with a friend. Embedded in channels that utilize short-form communication — web chat, a messenger app, SMS or social media — conversational selling is even more effective. 

Conversational marketing replaces the lead capture, qualification and contact process that is integral to sales with a conversation between the marketer and the prospective customer. The one-on-one approach usually plays out like this: Jordan just landed on your site. Let’s recap the steps it took Jordan to get there. First, she opened her device, navigated to your webpage through a browser and waited for the page to load. With thousands of digital avenues vying for consumers’ attention, it’s important to acknowledge that in seeking out your company, Jordan has already made a big effort. 

So how are you going to repay that effort? Through positive reinforcement, of course. A chat or messenger window pops up on your homepage, congratulating Jordan for making it this far. Then it asks Jordan what brought her to your company’s website. After her prompt response, Jordan is asked to share the role she plays at her company. 

The entire interaction clocks in at under 30 seconds, and guess what? You’ve just captured and qualified your lead. That’s conversational marketing, in a nutshell: enhancing the tried and true process of lead generation through automation and augmentation which increase engagement.

The principles of conversational marketing can be applied to both B2C and B2B contexts. Companies such as National Geographic, Starbucks and Whole Foods have embedded bots into messenger apps that serve a dual function; to convert customers through one-to-one interaction while providing them a utility. In the case of National Geographic, this utility was to answer questions about the universe through an Einstein bot that also promoted a new series. The Starbucks bot lets users make complex coffee orders while offering incentives and discounts. Whole Foods leverages messenger in a similar way by providing users with tasty ideas for dinner while leading them to the closest store to pick up ingredients.

B2B companies often use conversational marketing tactics to help them convert, qualify and set appointments for leads more efficiently. A process that used to involve upwards of ten steps; land on website, fill out form, become a lead in a CRM like Salesforce, receive several emails, eventually qualify and receive a call – now occurs in a short, three-step conversation. Drift is trailblazing the B2B conversational marketing arena with Driftbot, which connects leads with sales agents in order to book meetings instantly.

Conversational selling is the cousin of conversational marketing. But conversational selling does not simply want to make friends. It wants to close a sale, nurture customer relationships and increase lifetime customer value, all while customizing and up-selling products for the perfect ordering experience. If you’re thinking conversational selling is a perfectionist, you’re correct.

Conversational selling most often leverages chat, SMS and voice. Chances are you’ve encountered and engaged with conversational selling, especially if you’re under 40. Conversational selling can be a bot embedded in a messenger program, an automated menu delivered via SMS or interacting with an intelligent agent or live sales agent over the phone. Most often, conversational selling uses some form of Augmented Intelligence to optimize the conversation for the best possible outcome. Consumers’ preferences continue to trend toward messaging, making conversational selling via chat a winning combination. 

Brands that use conversational selling include Sephora, 1-800 Flowers, Jenny Craig USA and Hyatt. While the optimal outcome of a B2B sales interaction is often scheduling a call or demo, the optimal outcome of a B2C outcome can be completing a sale. B2C sales tend to be driven by emotion. That makes a one-on-one conversation a great way to connect and communicate with the customer on a human level. 

Conversational selling – whether implemented by a bot or live chat agents – can be optimized through data and conversational analytics generated by any company’s prior sales interactions. Intercom’s live chat for sales solution generates high quality leads by proactively reaching out to a customer that’s likely to convert. A/B testing, auto messages and tailor made ad campaigns make each conversation yield the best result. Language has never been more powerful.

Here are some takeaways to help you optimize your one-to-one sales efforts now:

  • Use automated menus and canned responses to get the conversation going. Your sales and marketing efforts have generated a lot of language so far. Trust us, we know. From countless email campaigns to A/B tested banner ads, every bit of language you’ve generated so far has created a corpus of data that can be analyzed to generate the best possible canned kick-off messages for any conversation.
  • Pay attention to platforms. What’s best for your B2C now, such as Facebook messenger, may be upstaged in the near future by WhatsApp or Kik. New APIs are emerging such as Google’s RCS Messaging and Apple Business Chat. Know where your customers are, where they’re going and follow them there.
  • Try humor, wit and emotional appeal. Crunch your chat logs for positive instances of these classic conversational devices, and add them to your live chat sales agent’s resources and bot scripts. A turn of phrase that elicits a smile or even a laugh can make a one-stop shopper into a lifelong customer.

About Co-Author Tony Medrano:

Tony Medrano is CEO and Co-Founder of RapportBoost, the leader in applying artificial intelligence to optimize live chat conversations in order to drive dramatic and sustained improvements in conversion rate, order size, customer satisfaction, renewal rate, average handle time, first contact resolution rate, agent retention and happiness and other critical contact center metrics. He can be reached at tony (at)

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Dani Apgar

About Dani Apgar

Danielle is a Co-Founder of RapportBoost.AI, and one of the world’s most successful enterprise artificial intelligence sales professionals. She led the sales, customer success, account management, and sales engineering teams for more than 3 years at Persado, a CNBC Disruptor Top 50 Artificial Intelligence company funded by Goldman Sachs and Bain Capital. She has personally closed six and seven-figure artificial intelligence/SaaS/ARR deals and has worked with companies like Microsoft, Travelocity, Caesars Entertainment, Pottery Barn, Expedia, and Zulily. Her clients had the highest rate of customer retention and satisfaction in the 200+ person company. Dani first worked with Tony in a Silicon Valley tech company in 1999. Dani was a founding Executive Director for Humans for AI, which aims to build the diverse workforce of the future leveraging the existing AI technologies. Dani volunteers and has traveled to Africa with Just Like My Child Foundation. Their mission is to empower vulnerable adolescent girls by enabling them to create healthy, self-sustaining families who prosper without further aid.

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