
This week’s Weekly Briefing was all about Storytelling. Jim Benton was joined by Doug Landis, Growth Partner at Emergence Capital, and a special guest: Chorus’s very own Devin Liu.
Setting the stage with data, Jim shared that top performers tell 20% more stories than the average performer. It’s clear that storytelling has an impact on getting deals across the line. But they’re used far less often than they should be. So, today, Jim, Doug, and Devin uncover the power of storytelling in sales, and how to use them to win.
“In the spirit of storytelling,” said Jim, “We’re going to try to tell stories the entire time.”
And they did indeed start with a story.
Jim asked Doug: “How does somebody get to be known as the ‘Chief Storyteller’?”
Doug said it all started at a former company, Box.
“We hired a new CRO,” he said. “He walked around the sales floor and asked how they position or articulate the value of Box. And what he heard was 20 or 30 different stories. Three things came to mind.”
1. Have a point to your story.
“It’s not bad to hear 20 to 30 variations of your own story,” Doug said. “The challenge was that there wasn’t a clear point to these stories. They were all over the place.”
2. Tell your own story or a story you really connect with.
“Everyone was trying to tell somebody else’s story. In this case, Aaron’s version of the Box story [the CEO],” he said. “And you have to be really careful when you’re telling someone else’s story and to make it sound sincere and authentic. Which is critical to telling stories.”
3. Your story should be about them.
“I realized that all these stories were super self-serving. It was all ‘us, us, us.’”
After this exercise, Doug went and pitched this idea to Aaron to change the way that Box talked about themselves, who they were, and what they did.

Top Performers Use More Social Proof.
It helped prospects connect with who we were and the value we bring to our customers.
Stories Win Deals #
“When we really infused the voice of the customer; and when we got really clear on the point of the story; and we taught everyone how to make the story their own,” said Doug, “it made it easier for the reps to own and articulate in a more authentic way. And it helped prospects connect with who we were and the value we bring to our customers.”
As an example, Doug shared the story he referenced during his days at Box.
“I tried to simplify things,” he said, “We were in the business of trying to make information available at any point in time. And that matters.
I remember Sue who was a mid-level marketing manager at Coca-Cola. She was divorced with two kids. And anytime her child was sick, she had to call in and take the day off of work because she couldn’t get her work done at home. But when she started working with a product like Box, she was able to get what she needed to do while still taking care of her family without taking days off of work. And that literally changed her life.”

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The best salespeople are more consciously aware of the stories they tell, when they tell those stories, and how to tell those stories. And how to tell them throughout the process.
Top Performers Use More Social Proof in Sales Calls #
The stories that sales professionals tell have to be told the right way to drive impact. We see that top performers include social proof in their stories 68% of the time. The average performer by contrast only uses social proof in 29% of the stories they tell.
Doug wasn’t surprised that the top reps use more proof in their stories. But, like stories, social proof has to be thoughtfully told to the right person.
“I define social proof as customer stories,” said Doug. “You identify customers that are similar to them. They use our platform and find a similar value that your prospect will find. The construct of social proof is that you need to highlight the contrast.”
The contrast in a story with social proof is honing on the point of your story. To help them see what is now versus what could be. “It’s crucial in helping people understand that there was a journey,” said Doug, “But it’s hard to do if you’re not consciously mindful of it.”
And that’s the ultimate point to storytelling: “The best salespeople are more consciously aware of the stories they tell, when they tell those stories, and how to tell those stories. And how to tell them throughout the process.”
Jim agreed. “From my early days in selling,” Jim said, “a customer had come back and said ‘this is like crack for salespeople.’. And the key was the story. It was who had said it and why they said it. Having that authenticity matters.”
“You can craft 200 stories off of that hook,” said Doug. “But what we’re getting at here is that Important tool is telling analogies and metaphors. We tend to drink too much of our own champagne and use our own words. And guess what? 90% of your prospects have no idea what you’re saying.”
“Using analogies and metaphors takes complex ideas and make them more easily understood,” Doug shared.
If you’re about to connect with someone, understand them #
Jim shared that he was asked to join a call recently with another CRO. “I wanted to be ready for it,” he said. He listened to all of the calls with this CRO so he could better understand what brought them to now.
“When we talk about storytelling, I always thought you had to be in it or see it in 3D. So I’m watching all of these recordings, and because of that I was really able to bring this deep understanding into this 15-minute dialogue.”
Jim asked Doug: “How do we get sales professionals to build a library of stories to tell them faster?”
It turns out that doing your research is important here as well. Salespeople need to know what stories they’re going to tell at each stage of the sales process and for each buyer.
“You need to be more thoughtful about what you’re going to tell to whom,” said Doug. “Because that story has to be relevant to them. That’s what makes platforms like Chorus so powerful. I could listen to stories from across the organization and put other people’s stories into this matrix. I would know what story to say when and in which situation.”
Telling stories is hard if you’re not thinking ahead of time.
“It’s hard to come up with one on the spot,” said Doug. “We don’t know what the point is so we ramble.”

When Should We Use Social Proof in the Sales Cycle?
Executives want to hear about their peers and their competitors, and how they are winning in this environment.
Telling Stories to the Buying Executive #
We know from previous Weekly Briefings that executives are showing up to more sales calls. And it seems that they want to hear stories.
When an executive buyer is on the line, social proof is used 16% more often than when they’re not in the meeting.
“We better be ready to go tell stories,” said Jim. He asked Doug what stories executives want to hear.
“Executives want to hear about their peers and their competitors, and how they are winning in this environment. Or how you may be helping your peers or competitors,” said Doug.
We had one shot with their executive team to get into this evaluation. Instead of leading with our differentiators, I shared customer stories.
How Telling Stories Wins the Deal #
Jim then welcomed one of Chorus’s top performers and Sales Manager, Devin Liu to share his experience leveraging stories to win deals.
“Let me give you a story about storytelling,” said Devin. “It’s a big piece of my sales process. It’s not about helping them understand all of the features you have. It’s how and why they use it and the impact. There’s no better way to do that but to give them an example of someone like them who found value.”
He shared an example from a deal he worked earlier in the year, in which storytelling to some executives got a deal over the line.
“We were deep into the evaluation process,” said Devin, “And we had one shot with their executive team to get into this evaluation. Instead of leading with our differentiators, we had a chance to shape the evaluation criteria. It was their first time leveraging tech like this. So I shared customer stories. I really focused on their key parts and key problems.”
He said that this wasn’t the only time he used stories either. He wove them in throughout the demo and each step of the process.
“I gave them relevant examples on how other people just like them have used it and the impact it drove,” he said.
The story he used? Well, without giving too much away, he drove home the real impact of Chorus playlists in onboarding to a Head of Sales Enablement by sharing a similar experience with a similar Head of Sales Enablement.
He didn’t name the customer specifically because he used them as a customer reference. “When the deal was done,” said Devin, “they reached out to me and said that ‘For the record, it was your reference that really pushed this over the line.’”
“Ultimately I was able to connect the vision to the reality for them, and for the impact on new hire onboarding,” he said. “Customer stories work.”
Doug highlighted a few things that Devin anchored his story around. “His story created contrast,” said Doug. “Here’s your world before Chorus. Here’s your world after Chorus. Contrast is a really powerful tool in the world of stories.”
It was the absolute highlight of my six months at Chorus. Just being with an iconic team, coming together. This is why we do this. It’s the journey of building these companies, and solving these problems.
Storytelling Lightning Round #
In a surprise exercise, Jim asked everyone to share a story on the spot. And they delivered. In any case, putting salespeople on the spot is just another day on the job.
Not only were they compelling, but they were effective.
They all carried three components of a narrative framework:
- Setting. A time and a place.
- Character(s).
- An outcome.
Doug started us off with his story about dinner in LA and learning the restaurant scene there in the midst of a pandemic.
“I felt like I was in Africa and we had just gone out hunting - they’re known for their gamey meats. It was awesome and amazing, and something I never thought I’d experience in LA over my first three months.”
Jim shared his journey with the Chorus leadership team after joining at the start of COVID-19 and universal remote work.
“On the last day of the quarter, I invited a leader over so that we can talk about messaging,” he said. “And the next thing you know there’s five of us sitting outside in Adirondack chairs with a nice bottle of wine, with heat lamps and globe lights. It was the absolute highlight of my six months at Chorus. Just being with an iconic team, coming together. This is why we do this. It’s the journey of building these companies, and solving these problems.”
Devin shared a story about his professional progression from an individual contributor role to a leadership role here at Chorus.
“I have one rep on my team who’s a superstar, Kora Graham. She was carrying the weight in terms of pipeline for the team. So I helped her get rid of those monotonous tasks and focus on the things that were really going to get her deals. It was a really fun experience working with her over the last few weeks of the quarter to really focus on the True North.
And she had her biggest quarter ever. It was the most rewarding part of my job moving from an Individual Contributor to Leadership. To see yourself be successful, but to also see someone else be really successful.”
After their lightning round, Doug suggested that sales orgs start team meetings by telling personal or professional stories. This will help train your team on the skills of powerful storytelling.
Tell Stories in Your Discovery and Demo Calls #
The first call in a deal is by far and away the call with the most stories told. And it starts to taper off as you continue down the cycle.
But if you are looking to tell stories throughout your engagement with a prospect, it’s important to know which stories to tell at which stage.
“At the end of the day,” said Doug, “we need to have a business conversation. In that conversation, I’m going to use examples of companies that are in a similar situation to show what their journey was all about and what the outcome was.”

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