How This 5X Founder Creates an Internal Culture With a “Crazy Focus” on Storytelling

How This 5X Founder Creates an Internal Culture With a “Crazy Focus” on Storytelling

As David Cancel puts it, they are “obsessed with story internally” at Drift. From the inspiration they’ve taken from the screenplay writing world, to how storytelling training is part of their onboarding, we dig deep into how he created this culture as the CEO.

David Cancel has penned two books, crafts a popular weekly newsletter, contributes to outlets like TechCrunch and Inc, and hosts a great podcast. But he’s not a marketer by training. In fact, he’s held plenty of other titles, from software engineer and CTO, to Chief Product Officer, co-founder, and CEO — perhaps not the resume that comes to mind when you picture a storyteller.

“Even though I always built products for marketers and for salespeople, I wasn’t a marketer or a salesperson. So I had to teach myself marketing,” says Cancel, now the co-founder and CEO of Drift. “I applied an engineering mindset to it and started with how people make decisions, reading all the books you can imagine on human decision-making, cognitive biases and social psychology. Then I started to work upwards to copywriting, understanding what does and doesn’t work. Then, I started focusing on how we think about marketing from a brand standpoint.”

That’s why a good story has played a pivotal role in Drift’s marketing from the outset — as Cancel has previously detailed in his newsletter:

“We didn’t want to talk about software, websites, or widgets. We wanted to tell a story. That’s why we used the analogy of an empty store. We talked about people spending all of this money on advertising trying to get people into the store, and then when the customer gets there and wants to buy something, there’s no one there who will talk to them. It made sense because we weren’t just talking about all of our great features. We were telling a story in a way that showcased the experience and outcome we knew our customers were looking for.”

What we found most interesting in our recent conversation with Cancel was how that storytelling remit has since expanded, shifting from a purely external exercise into a vital internal center of gravity for the company. Here’s how he tells it: “As we were scaling the company, things were getting misinterpreted. We were working on projects that we shouldn’t have been working on, and our customers were struggling to understand how we fit in their world. Inside, we were feeling all this pain as an organization. At first, I didn’t really see the root of it, I saw them as a bunch of different issues,” Cancel says.

“I was running around, obviously trying to fix each and every one of those things along with the team. But when I started to kind of zoom out, I quickly figured out that it all came down to missing the story. While we were obsessed with story from a marketing standpoint, it wasn’t until later that I saw the connection between storytelling and the pain that we were having internally.”

Here on The Review, we’ve previously written about the power of storytelling, sharing real-life inspiration from places like Pixar, IDEO and Netflix. But Cancel’s focus on the internal art of storytelling and how it’s a powerful tool in the CEO’s arsenal stands out. “I’m always trying to figure out what's the next version of myself. And every year that's been pretty different. And now more than ever, it's all about, ‘What are the few things that I can focus on that can help the team?’" he says.

"Now that we have all of these leaders in place, and we're about 400 people on the team, these days I’m trying to spend all my time focused on those zoomed out things: What’s our story? Not just the vision, but what is the story that we're telling for the next year, two years, five years? I really think about building that bigger story first, and how we can do a better job at storytelling — not only the story itself, but the act of storytelling and training on that internally,” says Cancel.

“Then and only then can we start to translate it into how we communicate to our customers, to our prospects on our website and every message that we write. What are the offerings that we bring to market? How are the offerings that we have in place changing? What are the new stories or how are we adapting those stories? And then what does the story tell us that we need to build next?"

This work is the easiest for me and the organization to ignore. But it's the most powerful. Because when we have communication issues within the company or with our customers and prospects, it all comes back to the fact that we didn't spend enough time trying to understand the story.

In this exclusive interview, Cancel gets more granular on how he created this internal culture centered around great storytelling. He shares five lessons on how to weave storytelling into all that your startup does, covering everything from internal training and specific techniques like starting at the end and focusing on the hero’s journey, to why CEOs should be editors and where he sources his inspiration.


Alongside their conversational marketing and sales platform, the Drift team has cultivated a community with Drift Insider, a free, on-demand online forum with classes, videos and exclusive content. “It's basically like Masterclass for marketers and salespeople,” says Cancel. “It’s a bunch of courses and videos that we've created internally and with third parties, but it was first built for internal use, all around this type of training that we put everyone who joins the company through — we try to teach a lot through internal video courses.”

Here’s how it got started: “In the early days of Drift, I was using WhatsApp all the time. It was easy to record and send videos quickly. And so I started to communicate to my senior leadership team mostly asynchronously through video and audio messages. First, I noticed that it allowed me to really think through what I was saying, versus just getting in a room with someone or having a back and forth in text messaging or a phone call,” says Cancel. “But second, when I created this artifact, obviously that could then be shared. And it was the sharing aspect that really made it an effective tool for us — all of a sudden we had old videos on different topics that we could share with people who were starting their journey at Drift in their onboarding process.”

During onboarding, everyone — not just those in marketing — goes through training, not only on what our story is, but on how do you tell a story? How do you give a presentation? How do you write copy? What are cognitive biases? How do people make decisions?

This form of internal storytelling led the Drift team to create a platform and then ultimately offer it as a product because they were using it so often. “If we have a problem, we’d make a quick video on what we sucked at, how we fixed it, the results, and what we learned. We’d share it with the team or make it part of onboarding,” says Cancel.

“Nowadays, the executive team uses it all the time, but one of the teams that probably uses it the most is the product and engineering team. They have videos about everything that they do, from new releases, and problems that they're working on, to all their meetings. And so embracing that asynchronous nature of communicating and having that artifact that we can store and share with other people over time has really helped with onboarding, getting everyone focused, and helping folks understand why we were making decisions, giving us an ability to be transparent in a way that we couldn't before.”

I would say our internal asynchronous communication is 80% video, 20% audio — it’s been massive for us. For me personally, it’s greatly reduced the number of meetings I have and increased the quality of my feedback.

But what does that training focus on? “One place that’s helpful to start is on how people make decisions. Forget about the tools for a minute. Everyone wants to go straight to the channels and get lost in the tactics of marketing. But what we figured out pretty quickly was that most marketers — even though they were super effective on different channels of demand generation or events — didn't really understand why the messages that they were using sometimes worked and sometimes didn't. So we began to internally first train on that,” says Cancel.

Cancel shares a specific example of what he means here. “We have an internal course on the Amazon product detail page. It’s the same template that they use for pretty much every product that they sell. And we break it down and say, ‘Okay, why does this page work from a decision-making standpoint?’ Because if you were to look at it just from a visual or UX standpoint, you would ask your designer to redesign that page. It would appear to be just a bunch of clutter, colors and things competing for attention — but you’d be removing every reason that that page works so well for them,” he says.

“If you start to look at it from how people make decisions, you'll see elements like the reviews and the photo and video uploads that hit you from a social bias standpoint of wanting to belong and be like others. And then there are people who want to make decisions immediately and they want everything right away. Things like, ‘We only have four more of these in stock,’ or, ‘If you buy now, we'll ship it to you by tomorrow at 1 PM’ trigger that. There's all these triggers over and over again for every single type that you see on that page,” says Cancel.

“And of course, most people are a combination of these types, so all these things work together. Charlie Munger once said that if you trigger more than one cognitive bias, then you get into this Lollapalooza effect. When you're triggering someone on multiple biases at the same time, that really changes how they make decisions.”

David Cancel, CEO and Co-Founder of Drift


While these good storytelling habits are well-established, Cancel is quick to admit that the Drift team is still building this muscle. “We continue to live that and try to push it — but that doesn't mean that we're great at it. It means that it's constantly an activity that we have to focus on,” he says.

For Cancel, this consistent focus brings a metaphor to mind. “I compare it to growing an English garden. The garden doesn't get built by just planting the right kind of plants. 99% of the work is pruning. It’s the same with trying to keep storytelling a focus. It never ends. There isn't a shortcut. We just drill it and make it a ritual,” he says.

“Pruning is always the painful part for me. Take this example: We just hired a new VP of product marketing. And so right now, it's been about zooming in and just tearing apart how poorly of a job we've done in specific product marketing work so far. That sounds simple, but it isn't easy because folks on our team have worked on that stuff. And so you're jumping in and trying to be helpful, but it's hard for people not to feel that in their egos, that shock of, 'This is how bad we suck at X, Y, and Z.’”

The only path to growth involves discomfort. It's easy to say, “I want to grow and learn,” but nobody wants to go through the uncomfortable part.

That’s the kind of work that often gets skipped over, particularly when scale sets in. “When we're all unde the stress of trying to build something, or we’re under a deadline, that's the easiest time to give up, take the shortcut, follow conventional wisdom, or just repeat something you did before. There’s a tendency to reduce things to the most scalable approach, which means checklists and best practices — we call them ‘plays’ internally,” says Cancel.

“And I found that we got to a point where no one was questioning any of the plays. No one was thinking about how to reinvent the process. They were just following the plays and completing checklists as quickly as possible. They cared about their work, but it became more about hitting the deadline and not about, ‘How do we make this better?’ Or, ‘Why are we doing this?’ Or ‘There's a message that worked last time, but will it work again?’”

It’s situations like these where leaders need to step in on the storytelling front, Cancel says. “I think a lot of my job has been over the years as an editor. I'm obviously not doing any of the work or a pretty small amount of the work, but I serve more as the editor of the voice — how we can get better on it, where we say it’s not good enough, where we push back and say we can do a better job.”

As CEO, I think of my job as an editor — noticing something, surfacing it and pushing people, trying to hold the team to a higher standard.

“That all sounds nice and easy and obvious. But the real work is actually doing it, not compromising, and doing that over and over again. And that's the part that makes all the difference. Because it's very easy to read something like this and be like, ‘Yep, it's a great idea.’ It's obvious everyone should do that, but no one does it. And that's the point of playing the role of editor and setting standards of excellence.”

But knowing when to swoop in with the editor’s red pen requires a careful balancing. Here’s how he thinks about that more tactically: “Each time that I notice something, I’m thinking, ‘Should have an executive on the team caught this? Should I be doing this? Should I stay out of this?” says Cancel. “Really, it’s about judgment and instincts. You’re trying to help people develop those instincts that in many ways mirrors yours. Here’s what I care about: Has someone actually asked the question? Can someone actually answer, ‘Why are we doing this?’”

Here’s why: “If I see something that doesn’t seem right, but we have a conversation about it and they can give a very thought-out answer, even if I completely disagree with the execution of it, I will defer to them. They probably have a hypothesis that I don't understand yet, but it's very well thought out. But most of the time when you zoom in, it's the opposite of that — typically when you talk to someone about what they’re doing, they find it very hard to answer that ‘why’ question.”


When asked for the storytelling techniques that have most influenced his skills over the years, Cancel offered up two: the practice of inverting, and sticking to the hero’s journey. We delve into each one below.

Start backwards.

“When it comes to being able to tell a story, we practice this technique of inverting everything, which we again learned from Charlie Munger. I love Munger because he simplifies everything. At its simplest, it’s just about starting backwards,” says Cancel.

“For the example he uses, he asks his kids, if someone won the world champion title at the age of 20 and then they won again at the age of 75, what was the activity or sport? And some of the kids couldn't figure it out, but his son started backwards — or inverted — and said, ‘Okay, if they won at 75, it can’t be a physical activity or require a high cognitive ability.’ And then he started to tick through the options. ‘Could it be chess? No, it’d be hard to be a grand champion in chess at age 75. But what’s close to chess? Checkers?’ And that was the answer. Instead of starting forwards with all of the sports and ruling them out, he inverted and focused on what would have to be true for the answer to be correct.”

But how has the Drift team applied this concept in the realm of software? “Our very notion of what we do as a company is that we've inverted,” says Cancel. As he’s previously written, Cancel and his co-founder Elias Torres followed Munger’s advice when starting Drift:

We were faced with the question: How would we stand out as the 6,830th product in the MarTech space? We looked for a common trait among all the products laid out across the MarTech landscape and found they all helped companies sell more. The vast majority were started in a time where the seller (the company) had all the control. They could focus inward on helping their own customers, also companies, sell more. They didn't have to focus on helping would-be buyers. But Drift was built in 2014 — a time when the power was shifting from sellers to buyers.”

Cancel expands: “Everything that we do at Drift, because we believe that's true, starts with the buyer perspective — not the company perspective, not the sales rep perspective. And so it's a fundamentally different way to start to build marketing and sales software, and tell that story."

Plot out the hero’s journey.

Beyond that initial company focus and origin story, Cancel and team have looked to other corners for story structure inspiration. “We started to study the simple things that everyone knows in terms of storytelling, most of which comes from writing screenplays. Take the hero’s journey from Joseph Campbell and its different archetypes. When we started our podcast, I was trying to figure out, ‘What are our characters? Who are we?” he says.

“Not that we are actually characters because it's 100% us, but rather, what do we need to emphasize so people can identify with this character? My co-host Dave was kind of a young marketer and it was more of a mentor-mentee relationship. And so my main character was that of the sage — I'm the old man who's got a bunch of stories and is trying to teach this young hero who's on the beginning path of his journey all of these lessons that I've learned,” says Cancel.

“So those were the two archetypes that we emphasized. It didn't mean that we were acting, but we knew that we had to follow a sort of story pattern for people to develop empathy or connection with us. And it's not just the podcast. We also do that in stories that we tell or in copywriting — we're always trying to figure out the hero’s path.”


But the inspiration for a great story doesn’t just come from the silver screen or pearls of wisdom from Munger — in our conversation, Cancel shared a few tech and business leaders with internal storytelling chops that he admires.

“Salesforce’s Marc Benioff is probably by far the best one that we admire and that we look to. One of the things I learned from Benioff was this idea of annual themes. He and the team worked nonstop on an annual theme, road testing that message in smaller events. And then finally that message would be locked in and ready for the world by the time they unveiled it at their annual Dreamforce conference. There's a series of tests and iteration that are happening along the way in public, getting it to a point that it's refined enough,” says Cancel.

“In his book, 'Behind the Cloud,' he talks about how they would implement that tactically, including things like, ‘How are we going to get that message out to everyone on the team? Are they going to memorize this?’ His book has tons of wisdom on how to operationalize, test and harden a message and then use that in your big reveal.”

Another one Cancel points to is the example of Patagonia. “We’ve long admired Yvon Chouinard. That story of how they founded the company and the ethos behind it had a big impact on us when we were starting Drift. Obviously, it’s a very different form of storytelling in the consumer product world, but it's clear that with that brand, you are buying a story more than anything else.”

Finally, Cancel highlights Frank Slootman, the CEO whose stock has been rising to even greater heights ever since Snowflake’s post-IPO success. “In some ways he is like another version of Munger — they can both break down the most complicated things to the simplest terms. What I get from Slootman is that it all comes down to understanding what the incentives are and how to design the incentives so that humans will act in the best way,” he says. (See this post from Slootman if you haven’t read it.)

Cancel reaches for a recent example of how this has impacted his thinking. “This came up at Drift’s recent quarterly meeting. We’re moving more into the enterprise from a customer base standpoint, and the one thing that we've never fixed is multi-year commissions. So no one had an incentive to actually sell a multi-year deal. That’s a painfully obvious one, but we weren't doing it and we were expecting a different outcome. So that's one that we just fixed recently and we're seeing the results of that almost immediately,” he says.

Cancel reaches further back in his career for a story outside of the sales org, where incentives are not as dominant. “At HubSpot, we had a traditional hierarchy within product, engineering and design, where the head of engineering and the head of product work together to build the product and solve the technical issues. And what we saw was that even though they were communicating incredibly well and had shared goals, things weren't working as well as they could have. Each team started to optimize for the things that they felt were more important,” says Cancel.

“An obvious example would be engineering's focus on refactoring and building internal tools, and the product team wanting to focus more on customer problems. After a closer look, even though the goals were the same, they were naturally incentivized in two different directions. So I unified product to be one organization, getting rid of product and engineering. And everyone moved to work for one single person, and that person set all the goals for the team,” he says.

“That seems simple, but it was a big way to get everyone to focus on one thing. We started to measure everyone on customer metrics, including engineers. So every engineer had to spend a certain amount of time talking to customers. Older engineering metrics based on building and shipping weren’t tied to those customer guardrail metrics that you had to move as a team.”


“Another important move we’ve made is embracing the idea of rituals — it’s one of the best things that we've done within Drift. They give people comfort that there’s a place where things are going to be discussed, that there is a format to something that they can count on. Rituals ensure that we stay true to our vision and culture, and have a place to tell these stories internally,” says Cancel. As he notes, it also offers up a venue to tell and reinforce that story of why the company is doing what it’s doing.

Here are two of the rituals Drift has come to rely on:

  • Monday Metrics. This 20-30 minute meeting starts the week. The team reviews the metrics from last week and outlines what they need to focus on from each functional area for the coming week. It’s also where “Drift Love” gets shared, including customer praise from social media or emails.
  • Show and Tell. This weekly capstone started out during Cancel’s days at Hubspot, where the product and engineering teams could “show their work” to the rest of the organization. It’s a tradition he’s continued at Drift, expanding it so that every function presents. “Every week at 3PM, a different person is chosen from each team to present. There’s competition and awards. It’s our most effective communication channel and none of the executives speak at it. We have a Q&A at the end of it, but it’s self-organized — the team is running and evolving this meeting.”

As Cancel writes, bookending the week with these two meetings allows the team to answer two questions: How did we do? What did we actually make?

This article is a lightly-edited summary of the key takeaways from David Cancel’s appearance on our new podcast, “In Depth.” If you haven’t listened to our show yet, be sure to check it out here.

Cover photo by iStock / Getty Images Plus / francescoch.