David Cancel: Hypergrowth Entrepreneur

Listen to this article

By Evan J. Cutts

In the age of smart technology serial entrepreneur and hypergrowth expert, David Cancel recognized an opportunity to recenter the customer in B2B sales and marketing. As co-founder and CEO of Drift, the first conversational marketing platform, David believes A.I. and bots are the keys to creating a more personalized experience in the internet age.

A businessman of many talents, David Cancel is also an influential podcast host (Seeking Wisdom), blogger, and the best-selling author of Conversational Marketing. David was named the top-ranked CEO by USA Today and has been featured by media outlets such as The New York Times, Forbes, Fortune, Wired, and Fast Company, and has guest lectured on entrepreneurship at Harvard, Harvard Business School, MIT, MIT’s Sloan School of Management, Bentley, and other universities. In the following Q&A, David offers his exclusive insights into Drift, entrepreneurial leadership, and more. 

EJC: Can you tell me more about your role as Co-founder and CEO at Drift?

DC: As CEO of Drift—as with any hypergrowth company—my role evolves every two or three months. And one thing in particular that has changed has been getting out of the “weeds” a bit.

For example, my natural tendency is to want to get deep into the details of the product, marketing or other areas. But at our current size, about 300 people, I recently realized I needed to change this pattern—and spend less time at my desk and more time externally and also internally working “on” the business instead of “in.” Because I recognized that those are the areas where I can really contribute and have a larger impact on Drift. 

What inspired Drift?

My co-founder, Elias Torres, and I started Drift because we realized that there had been a fundamental shift in the world. We realized that we used to live in a world where a company could dictate the buying process, and get back to you whenever they wanted. They had all the control. And all of a sudden, we were in a world where there were seemingly infinite options available and access to more information than ever before. So, companies needed to focus on the buyer. And whoever made it easier to buy, would win. That’s why companies like Amazon, Netflix, and Uber have been so successful and beat out companies like Blockbuster, Borders, and taxis; they recognized that if a buyer didn’t like an experience—they could just move on to one of the thousands of other options available. 

But there was one industry that wasn’t changing to meet their customers where they were and that was B2B sales and marketing. So with Drift, we set out to change that and create a better buying experience. 

US society today seems to be equally excited and anxious about Smart Technology (AI, Machine Learning, Bots, etc.), how does Drift succeed in connecting people as opposed to alienating them?  

One thing we realized when we started Drift is that people had become so obsessed with metrics and analytics that they’d forgotten about the actual people they were serving. And we wanted to return to the core of what the buying process has always been—a conversation between the buyer and the seller.  

So one of the first things we did at Drift was removing all forms because we thought those alienated customers—and didn’t make the process customer-centric. Now, people can engage with our bots—or speak with a human. And even when a chatbot is doing the talking, you end up learning more about potential customers than you would have otherwise. 

Ultimately, we believe the most successful AI is when humans and AI can work together to maximize the performance of every team and provide the most value to the customer.  

What is the biggest misconception about what you do?

I’d say this goes back to your previous question—that because we have bots and AI it’s not a personalized, human experience. But that’s actually not the case at all. We believe in making the internet a conversation—and in making something that was a more anonymous experience before, something more like what you would experience face-to-face.  

Looking ahead, how can organizations and entrepreneurs use technology to ensure they remain relevant and inclusive as the social and cultural landscape shifts in the US?

It’s no secret that hiring practices are not inherently inclusive. And prioritizing diversity and inclusion from day one is vital to any organization—because building a diverse company is key to better serving diverse customers and communities. 

At Drift, we have partnered with Hack.Diversity which helps us recruit Black and Latinx computer science and engineering students—and helps train, coach and mentor both us, and them. We also have someone on our recruiting team focused on sourcing diverse and inclusive candidates, and use She Geeks Out as a consultant to our practices. 

Beyond this, we also believe that companies have a responsibility to help close the gap by supporting organizations that are looking to build a more inclusive business community. That’s why we recently launched the Drift Charitable Fund, which works with STEM programs like BUILD and Building Impact to help prepare the workforce of tomorrow.

As a serial entrepreneur, how do you define success? Is it just about the sale or is success deeper than that? 

I believe that a company is 99% people, 1% everything else. And so I look at success as whether our customers are happy, and whether our people at Drift are learning and feeling fulfilled.

I also focus on improving every day—and helping the people around me improve. So I measure my success based on those factors, and how I learn from my mistakes. 

In your opinion, what skills are necessary to be an effective leader? What do these skills look like in practice?

Again, to me, it all comes down to the people stuff. So an effective leader understands their strengths and weaknesses and also understands the same about the people they work with. They lean into their core strengths and then surround themselves with people who are equally strong in other dimensions to balance out their own weaknesses. 

How are millennials and Gen Zers impacting your industry? 

For the past two years, we’ve done a survey and report about the state of conversational marketing. And what we’ve learned is that actually both millennials and baby boomers have high expectations—and see the benefits of chatbots. So I believe that chatbots aren’t just for millennials (or Gen Zers)—they have the potential to improve online experiences for all buyers, regardless of their age. 

In your opinion, what does it mean to be a person of Color in 2019?

I feel very fortunate to have the success I have had. I was raised by an amazing single mother in Queens—but I just didn’t know what was possible outside of Queens. So now, it’s my mission to show others what is possible beyond where they are today—through mentorship and support—and hopefully inspire a future generation of founders, entrepreneurs, and leaders.