Chief Digital Officer and CIO, Hagerty: People who Think Like Entrepreneurs Can Significantly Impact Large Corporations

Kelly Smith, Chief Digital Officer and CIO at automotive lifestyle and membership company Hagerty, talks to Leonard Maganza, Chief Customer Officer at Syniti, about how Smith started his career in Seattle when the internet was first taking off, which proved to be serendipitous for him. Since then, Seattle has grown into one of the major innovation centers in the U.S. The Angel and Venture communities were robust in Seattle as well. So trying entrepreneurship was a natural transition for him.

Smith often jokes with his team about the inherited entrepreneurial baggage they have to bear due to Seattle's natural entrepreneurship influence. But he is clear that it's shaped some of his perspectives at large companies like Starbucks. One of the things that Kelly has realized is that people who can think like entrepreneurs can have a huge impact on a company, using skills like thinking outside the box, being proactive. He tells his team that the biggest opportunities fall between the gaps of an typical workchart. So people who are ready to do anything to move the needle are the big influencers. He calls these people "intrepreneurs." Intrepreneurs are like entrepreneurs, people who tend to have an appetite and interest to learn more and deliver more. They want to create an environment for intrepreneurs to thrive.

Digital transformation journeys are quite difficult and complex and Smith speculates that only about 30% of digital transformation efforts actually mature and work out. An organization has to have a clear strategy, and it should have a commitment from leadership from the CEO down into the middle management layer. It has to also recruit new types of talent and put them in the right place. You have to have an agile governance mindset, to persevere despite setbacks, adapt based on learning, failing fast, you have to have a handle on data. To get all these things right is difficult, but it's the hallmark of an interpreneur.