Hi Marley’s Newest Board Member, Scott Stephenson, on Culture, Coaching, and the Next Era of Insurance

Hi Marley’s CEO and Co-Founder, Mike Greene, recently welcomed Hi Marley’s newest board member, Scott Stephenson, for a fireside chat. Scott spent more than two decades leading large-scale transformations in the insurance ecosystem, including his tenure as CEO of Verisk. He has deep experience navigating the heavily regulated insurance landscape.

Their wide-ranging discussion explored how to lead through change, from the rise of big data to today’s AI applications, and what Scott is most excited about for Hi Marley’s future.

The Importance of Coaching and Leadership

From basketball coaches to career mentors, Scott shared how those who guided him throughout his own path informed his business leadership philosophy. During one particularly memorable childhood encounter with a fifth-grade basketball coach running repetitive drills, Scott was told, “You don’t have to worry as long as I’m correcting you. If I’m not correcting you, you know I don’t care anymore.”

Scott drew from this experience a lesson about the value of investing time and energy into members of his team.

According to Scott, building a great team starts with great human leadership. “One of the things I believe fully is that a great team will take a C business and turn it into an A business. But the converse is also true: a C team will take an A business and turn it into a C business. That’s why culture and leadership are so important.”

He described his leadership approach as “optimistic” and grounded in a strong belief in others.

Knowing that coaching is incredibly important in business, but takes a lot of energy and effort, Scott still makes it a priority as a leader. “Coaching is not instructing,” said Scott. “It’s helping someone else define their highest and best.”

Embracing a New Context: Leveraging an AI Approach

Big data was the backdrop of an earlier era of industry transformation, but now there’s a new moment of opportunity: AI.

“Insurance is a heavily regulated industry,” Scott said. “Regulators don’t want to suppress innovation, but they also don’t want to approve something they don’t understand. They see the value, but are cautious.”

Still, Scott believes there are three practical ways to position a business for success in this new era. First, build systems that connect AI safely to the right tools and data — so the technology works with what you already know and trust. Second, make sure AI draws from verified, reliable sources, so its outputs can be explained and stand up to scrutiny. Third, use AI to move faster and build smarter, while keeping humans in the loop to review and guide the work.

Scott suggests the best place to start is with where we are today, taking stock of what we’re already good at, and how we can be better. “We need to take both inductive and deductive patterns of thought – look at both the big picture and the details before deciding where to go next.”

Across each wave of change, Scott emphasized the same principle: in insurance, innovation only matters if it strengthens trust.

A Leadership Playbook for Industry Inflection Points

When Scott stepped into a CEO role in the early 2000s, he faced a familiar challenge in insurance: how do you evolve a trusted, service-first organization without breaking what customers rely on?

“Everybody in the company thought of it as a service. But this is 2000, and we’re at the dawn of Big Data,” recalled Scott. “On my first day, I said, ‘This is a data analytics business’.” Under Scott’s leadership, the organization went through a meaningful culture shift — reframing how teams worked, how value was defined, and how innovation could scale while preserving reliability and trust.

Hi Marley’s Future

As a final thought, Scott shared what motivated him to join Hi Marley, including that he was drawn to Hi Marley’s culture and adaptability, specifically its customer service.

“It’s clear that Hi Marley is just obsessive about customers, which is the greatest virtue that a company can have,” said Scott. “I did my due diligence out in the market. I asked current and prospective customers about their relationship with Hi Marley and received consistent positive responses. I’m excited about working with a team full of bright, well-rounded people.”

As for motivation, “A lot of society’s progress is just one innovation after another. And we all get to add to that. I just want to make my contributions until I’m not here anymore,” said Scott.

Mike Greene ended the fireside chat with a warm welcome to Scott, “You’ve already put a couple big dents in the universe, so we’re excited to have you alongside us to put another big dent in the universe.”