CEO Spotlight

Initially influenced by his father in the insurance business, the CEO of Rollo Insurance emphasizes the importance of values, family, and integrity. The company’s growth to over 60 offices across multiple states was strategic, aiming for stability and protection against future challenges. The “God, Family, Country” philosophy reflects the company’s core values, which have remained consistent since its inception. Jason and his team often highlight the great importance of genuine client relationships, treating clients as individuals, and the importance of insurance in society. As with any good organization, Rollo Insurance seeks to ensure that their culture and values are maintained as they continue to grow. The agency also prioritizes hiring the right people because a business can only be as good as those within it. Likewise, Rollo Insurance focuses on providing personalized service and addressing clients’ needs, rather than just selling on price.

Let’s go back. As Jason says, “It all started from a notepad almost twenty-five years ago.” What began as a love for people and protecting what they love most, Rollo Insurance Group, Inc., still exists today for the same reason, although now the family has grown to over 60 office locations.

But it didn’t start with almost 60 offices. It started with one office, built on the right values, focused on family and integrity. We sat down with Jason Rollo (CEO) to discuss the origins of Rollo Insurance, his personal insurance career, and keys to sustainable growth for a company that has expanded from one office in a town of less than 3,000 people…to offices across Texas and multiple states. 

Growing up, Jason’s dad (Sonny Rollo) was successful in the insurance business, so Jason learned firsthand how to interact with people and establish long-lasting relationships. His father showed him how to take care of people. They might be clients, but they were people first.  Jason is one of very few people that grew up with the goal of being in the insurance business himself one day. Jason started with Farm Bureau in 1999, thinking the captive insurance world was all there was. He enjoyed his career with that company and worked hard. But the independent insurance route soon became his life goal.  

A friend that ran track with his dad in college (at Baylor) hired Jason to start and run an insurance agency in Italy, Texas working with small banks. Jason left Farm Bureau on good terms and started and ran that agency for five years. He later bought that agency. “Branding Iron Insurance” was the original name, officially founded in 2000. After buying another agency in Fairfield, Texas, Branding Iron Insurance became Rollo Insurance Group, Inc., in 2004. “It was crazy,” Jason says of the business’ origins, “It’s just been a unique ride.”

Jason knew the agency needed to get big enough to have offices in different places because of volume commitment. He didn’t fully see today’s 60 plus office locations, but he did know that in order to be protected for the future, it couldn’t just be one office. The small agencies were going away because it was too difficult to compete, so Jason developed the platform for the future success of Rollo Insurance. Even in the midst of all the growth, Jason says, “I’m thankful for the way I grew up. I was instilled with the love of ‘God, family, and country.’” 

Jason also speaks about his family’s involvement in the agency, “BJ, my wife, started doing the books for free. We didn’t have any money to pay her and as we grew, she went all the way to CFO. We received our first check in September of 2000 for $174. That was our first income from the business. I mean, we have coffee pots at the office that cost more now. I couldn’t even afford a cup of coffee back then. But we’re still the same people. Our integrity is not for sale.” 

On the twelve Rollo Rules, Jason says, “We’ve been following these rules for many years. We just didn’t codify them. And so, if you care about people, then you actually get in and you look at their needs. You’ll treat them more like clients versus customers. You ask questions, you see what their needs are, and what they’re wanting to protect. You’re not just selling on price. Price matters, but it’s not the only thing you sell on. Hence, the difference is REAL, right? Rates, education, assets, and life. Real means genuine. You are who you claim to be and you sincerely care about people. If that’s the case, then it is going to matter what they need. You won’t just sell them something. We protect their success and what they’ve worked hard to earn.” 

Jason also speaks about the importance of hiring individuals that hold the same values as Rollo Insurance. “Basically, as we grow, making sure we bring people into the culture that fit and who hold to the same value system of caring about people as individuals and not just treating them like some number.” 

“God, Family, Country” served as the building blocks of Rollo Insurance and that slogan still is its foundation today. Jason says of those guiding principles, “That particular phrase, it’s our foundation, our backbone, and it goes back to values. Character-based-values is what we’re trying to say there. And when you have that, you don’t lose your way. As we grow, we are not going to lose who we are. We believe the difference is real, because we believe we (all of us) are REAL, genuine, hard-working people, trying to make our communities a better place to live.”