Declaration of Independents: Jackson Rollo

• By: Will Jones
• June 1, 2026

Jackson Rollo

President

Rollo Insurance

College Station, Texas

Jackson Rollo did not grow up dreaming of insurance. But like many second-generation leaders, once he found his way into the business, he stayed because of the relationships, responsibility and real impact independent agents can have in their communities.

Now president of the agency, he is focused on growth that puts people first. His vision is clear and increasingly rare in a shifting market.

“Long term, we want to be the standard for family-run agencies,” he says. “As consolidation increases, truly family-owned agencies are disappearing. We want to fill that gap.”

Advantages of being family-run?

The biggest advantage is built-in loyalty and trust. Your family knows you better than anyone. They push you, support you and hold you accountable. That dynamic accelerates the kind of culture most businesses try to create.

Building credibility as a young agent?

The key is showing genuine interest in your client’s business and life. Be professional, show up in person when you can, look people in the eye and shake their hands. Those fundamentals matter and help you stand out quickly.

Harnessing artificial intelligence (AI)?

It’s part of our toolset, but we are intentional about how we use it. We see AI as an efficiency multiplier that allows us to compete with much larger agencies while staying relationship-focused.

First and foremost, client data security matters. We are custodians of sensitive information and we only use tools that meet that responsibility. More generally, AI will either reduce headcount or massively increase output. We have chosen the second path. Our goal is to make our team of 60 perform like 180, not shrink the workforce.

How did you get into the insurance industry?

Growing up, I had no interest in insurance at all. I wanted to be an attorney, work in contract law or even end up at Apple. That was the plan. I graduated from Stanford early, had a year before law school and was about to get married. My dad, who has always been a mentor to me, suggested I spend that year learning the family business so I would at least understand it if I ever came back as an attorney.

Once I had the maturity and context to understand what insurance actually is, I fell in love with it. I loved the relationships, the freedom it creates and the impact you can have. Over time, I also fell in love with building a family business, especially the leadership and operational side. I realized law school was not for me and moved into a management role at a young age. I’ve never looked back.

How do you navigate working with family?

It works for us because we can separate business from family. We can have a heated discussion in a meeting and then go to dinner together as if nothing happened. However, working with family does not remove emotion from the decision-making process.

Success comes from understanding strengths and respecting roles. Not everyone can or should hold the same position. That mindset has become part of our culture and has extended beyond just family members to the entire team.

Advice for other young agents?

The biggest mistake young agents make is pretending they have experience they do not have. Admitting you do not know something, then finding the answer and delivering on it, is a superpower. Clients do not expect you to know everything. They expect you to be resourceful and competent. Age is not the differentiator. Work ethic, curiosity and follow-through are.

As a younger agent, you also have advantages. You can absorb information faster, adapt more quickly and challenge the “we’ve always done it this way” mindset.

How are you using technology in your agency?

We view technology as a tool to serve people, not replace them. Every technology decision we make is based on one question: Does this put time back into our teammates’ day so they can better serve clients? If the answer is no, we do not pursue it.

We have invested heavily in systems that streamline intake, communication and workflows. Phone systems, CRM integrations, automated emails and backend tools all exist to eliminate manual, repetitive work. That gives our team more time to build relationships and show up for clients when it matters most.

Approach to AI?

First and foremost, client data security matters. We are custodians of sensitive information and we only use tools that meet that responsibility.

We believe AI will either reduce headcount or massively increase output. We have chosen the second path. Our goal is to make our team of 60 perform like 180, not shrink the workforce.

How do you build a healthy workplace culture?

Culture is not a feeling. It is values, standards and beliefs put into practice. As we grew rapidly, we realized we needed to define our culture so new team members understood it immediately. That led us to create the Rollo Rules, which are 12 core values that guide how we operate.

They begin with “God is good, and you should be too,” and end with “Do right. Period.” Everything in between reinforces relationships, accountability, humility and continuous improvement. Those values are our filter for hiring, decision-making and daily operations.

What are your goals for the next few years?

Our goal is to grow one good office and one good teammate at a time. Growth matters, but people come first. If we bring in the right people and allow them to build a legacy, everything else follows.

One specific goal is to have 10% of our team be second-generation employees. If parents thrive here, their kids should want to build their careers here too.

What is your favorite thing about being an independent agent?

It is the freedom and the control. We control our destiny. Success or failure is a result of the decisions we make. That responsibility is heavy, but it is also empowering. We believe independence creates opportunity and we are willing to bet on ourselves and our ability to adapt.

Will Jones is IA editor-in-chief.