Dan Kaplan is a native New Yorker and a twenty-plus year veteran of McKinsey & Company and Sapient. Most recently, he was part of the team that built WeWork’s global and first Deloitte practice, @WeWork, the first “workplace as a platform.” From there, he helped launch and build Uber’s first consultancy. He now works as an independent business and management consultant, writing on how culture is forged and conditions successful organizations through the lens of his work at Singularity University.

We recently sat down with Kaplan for a deep dive into his experience on all three of the hottest areas of marketing automation and one of the most impactful, Twilio.

How does marketing automation fit into a strategy for expanding your brand online?

High user expectations and the shift to mobile have led marketers to explore new models of brand-to-consumer communication. Use of cognitive technology is expected to grow three-fold from 2018 to 2025 in the US to encompass over $600 billion, with the number of “pharmacies” rising to 140 million by 2025. For this reason, it has been clear to marketers for some time that they need to find ways to scale their marketing efforts online to survive. Marketing automation makes it possible.

What were the biggest challenges during the initial phase of growth of WeWork Labs?

There are always challenges when you try to launch a new business in a new industry at a new place in time. For example, your competitors and competitors that aren’t yet launched are going to be lurking to learn what you’re doing to see if you are planning to launch your business and stop you. Getting out and about on-demand city tours was difficult, as sometimes in certain large cities, the best tour agents with a big audience may not be able to get visas for a few months. Building around managing the real estate organization would be a challenge.

How did you manage being a part of a marketing automation startup and still be able to focus on your day job when needed?

Prior to WeWork Labs, I was a client consultant at Sapient, where we used this term “catalyst-generation,” or taking an idea in a web page and quickly creating proof of concept that would be offered to the client as part of our work on the project. At Sapient, clients turned me into a marketing automation freak. After coming out on the other side of a start-up, it was fun to be part of building, growing, and now growing WeWork Labs. During WeWork Labs’ early years, there were almost no peers to my work, especially when I’d ask an analyst in an early company that was in a similar position, “How is marketing automation used in a company that was not growing as quickly?” “People are slow.” “You have to explain this to people.” “They have to understand the different components and the metrics.” These are things you just don’t see in a different company in another industry.

Twilio has been the answer that set the stage for the entire tech industry to look at this space. What can you say about Twilio’s success and how was the initial chatbot set up and why the change?

In 2014, when we were working on the last version of a Twilio software product that was intended to power businesses’ marketing automation and virtual assistant platforms, there was a shift in focus. Customers wanted chatbots, and we were not yet a chatbot company. The initial technology had less advanced latency. For example, in 2014 it would take a 60 minute window from what we could program our product to what the end user would have to tell it. I remember when we were shipping the software and complaining about the scheduling of voice-overs, people (at this point) were so surprised that one day, “Hey, I just said, ‘hi’ in my app and just a half hour later my phone rang and someone picked up.” Since that time, conversations with customers have not slowed, and today live chat is the number one consumer interaction with the product.

Today, a customer will have 20 minutes of customer service, and then we expect to have the chatbot continue conversation with them until they are ready to move on. Chatbot technology changes how you are both a customer and a partner. In-depth personal service is a major growth opportunity for marketers in the digital economy.