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Get Started with Conversational Marketing: A Summary of Connor Cirillo’s Experience Inbound Session

Author: Stephanie Santoro

Connor Cirillo HubspotAnother Experience Inbound has come and gone! With so much information packed into one event, it can be tricky to see everything you wanted to see.

We’d hate for you to feel like you missed out, so we’ve put together a session summary of Connor Cirillo’s How to Actually Get Started with Conversational Marketing.

Connor Cirillo is a Conversational Marketing Manager at HubSpot, which means he works in all things conversational marketing including helping marketers actually get started with implementing these tactics in their strategy. So let’s dive in!

Why Implement Conversational Marketing?

A great question! And one Cirillo addressed right away in his presentation.

“Most businesses make it hard to do business. They make prospects jump through hoops and processes like never before. All these little things slow down the customer journey. At HubSpot, we call anything that slows down the customer journey "friction". It’s the opposite of anything that makes it easier to do business, or “force”. Today is a bad time for businesses to have friction, because prospects don't tolerate it like they used to.” - Connor Cirillo

Consumers have more options than ever in pretty much every industry, and thanks to technology we’re evolving to favor the most convenient of the options presented to us.

Consider This…

Back in the 90s if you wanted to watch a movie you didn’t own, you took the family down to good ol’ Blockbuster video. If they happened to have the video you wanted in stock, great! If not, you found something else to bring home and that was that.

Blockbuster_netflixToday we have Netflix. You don’t have to worry about leaving the house, bringing a movie back on time, or any of the other minor inconveniences of physical movie rental. To bring it even further, Netflix used AI to make suggestions for you based on your watch history.
Almost like you’re having a conversation . . .

Basically, expectations have changed. Consumers demand that processes become easier. Conversational marketing is the key to reducing friction in the buying experience.

This is especially important in a B2B setting, where we have been conditioned to expect friction. Many assume it’s just the cost of doing business. But friction is a silent killer, and all you B2B marketers out there may be losing more business than you think because of it.

Let’s Look at Friction in Marketing and Sales

Let’s look at how well-intending marketing teams can get it wrong.

  • Content - Many sources of friction with content happens when we assume people can digest everything we’ve written.
  • Website - Can your website answer every question a potential customer may have? If not they may give up on your product or service.
  • Email - Many marketers make the mistake of treating email as an end to the conversation, instead of continuing it.

This friction doesn’t stop at the marketing process, it continues into the sales process as well. One of the most common mistakes in sales is that they get the "when" wrong.

When throwing a surprise party, you don’t yell “SURPRISE!” before the guest of honor even gets home, and you don’t yell it a day later after the party has ended. There is a time and place for you to jump out behind the couch, noisemakers in hand.

“Prospects aren’t looking to be told to and sold to, they’re looking for help making sure this is right for their business.” - Connor Cirillo

sales and marketing conference

So what does a convenient customer journey look like?

  • Marketing - Get to know prospects and build the relationship that they want. Answer their questions and find out how you can help them right away. Use communication to find out where they are today, where they want to be tomorrow, and how you can help them get there.
  • Sales - The customer decides the right time to talk to sales. Once they do, both sides hit the ground running to find a solution that makes everyone better off.
  • Service - Once someone becomes a customer, your brand should act as a trusted guide every step of the way.

Conversational Marketing Removes Friction, Allowing You To Do More Business!

“Conversational means meeting people where and when they are in a natural way. You may have heard this in the context of marketing, but conversational is more than one department. It’s a shift in thinking to value the relationship and overall customer experience. Someone’s entire customer journey should be easy.” - Connor Cirillo

Conversational marketing sounds great, right?! So why are so few businesses doing it?

Realistically, it’s because they got a lot of other stuff going on. Most marketers are worried they don’t have the time, or the technical and design know-how to manage it and they won’t be able to fit it in their schedule to learn. And if they did, where would they start anyway?

All valid concerns, but conversational marketing is actually a lot simpler than it seems!

So what is the best way to actually get started with conversational marketing? Simply, adapt what you’re already doing.

You know your customers, and what roadblocks they face throughout the buyer’s journey. As an inbound marketer, it’s your job to educate them and find solutions to their problems and reservations. Now you need a way to modify the process so that it becomes an easy conversation about finding the best solution.

Connor’s inspiration for getting started with conversational marketing? Clippy, Microsoft Office’s talking paperclip.

Clippy Microsoft Office

multiple choice optionsClippy helped you navigate tools, troubleshoot and gave you recommendations depending on your project. Sounds helpful right? From here, you’ll combine the spirit of Clippy with a Pick-Your-Own-Adventure book. Anticipate the problems people will have throughout the buyer’s journey, and create multiple choice options to solve those problems.

Simple as that! You’ve started with conversational marketing.

The North Star Metric: Your Guiding Light In Building Helpful Conversations

“While you think about getting started, stay focused on how you can get people to where they want to be in a more efficient way. Make that your north star. Building out chatbots and live chat is only as helpful as the problem you’re solving. The metrics that signal success might change with each program, but the mindset should stay the same.” Connor Cirillo

Your goal with conversational marketing should be to get people where they want to be in a more efficient way.

Consider a pricing page on a website.

Your prospect is there because they want to know about pricing, but they also have questions related to pricing. Challenge yourself to solve for the three most common related questions and it will go a long way in easing the buying process. Always keep this in mind when working through conversational marketing.

conversational marketing

Combining The Human Touch with Automation

Humans are wonderful complex creatures, capable of solving lots of different complex problems. The issue is sometimes they have too much on their plate and can’t solve the problems prospects are coming to them with.

When considering where to add automation and conversational marketing think about your humans. What’s the most mind-numbing part of their day? Think how much better their day would be if they spent it helping people, instead of collecting and logging email addresses. But knowing how much automation is too much, especially when getting started, can be tough. It’s important to find the perfect balance between human and automation.

"Often, the answer of “humans or chatbots” is “yes”. - Connor Cirillo

humans or chatbots

This brings us to Cirillo’s Theorem of How Much To Automate. The more delicate a part of a conversation is, the less of that part you should try to automate. Finding the right balance will tricky, but you'll find the sweet spot with practice.

Theorem of How Much To Automate

Once you find that balance between automation and human assistance, life will become easier for both your prospects and your team. Win win!

How to Get Started with Conversational Marketing in Five Easy Steps!

Need the Cliff Notes version? Here you go!

  1. Start with simple technology and build over time.
  2. Anticipate what people need and make it more efficient to get there.
  3. Focus on automating common problems with standard outcomes.
  4. Free up your humans to focus on complex human-stuff they’re great at.
  5. Use context at every step to make the whole experience more natural.

“Be the one to remove friction from marketing, sales, and service processes. Make it easier for your business to do business. Go actually get started with conversational.” - Connor Cirillo


We were so grateful Connor was able to join us for Experience Inbound 2019 to share his expertise! If you're looking for more conversational marketing resources we recommend: 

Chatbot Scripts: A Step By Step Guide


About the Author:

Stephanie Santoro is a Marketing Coordinator at Stream Creative.

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