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“OUR NICHE IS PEOPLE”

October 17, 2025
“OUR NICHE IS PEOPLE”

Left: Rollo Insurance Group has truly been a “family” endeavor. Co-owners B.J. and Jason Rollo (in doorway) with their four children

from left, Jackson (with his wife, Kate, and their children), Jenna, Julia, and Josiah (with his wife, Nikki, and their child).

Family-owned Texas agency is growing

“one great location at a time”

By Dennis H. Pillsbury

Photography by Melanie Maganias Nashan

“We’ve got something special here,” says Chief Strategy and Talent Officer Keith Lane about Rollo Insurance Group, Inc., headquartered in College Station, Texas. “We have all the advantages of a larger agency in terms of markets, coverage options, and scale, yet at the same time the local presence of a small agency that focuses on the local people and local community it serves. 


“Our distinctions come from a much deeper sense of purpose, a voluntary and individual duty to truly serve clients in a way that emphasizes both loyalty and personal trust,” he adds.

Jason Rollo, founder and CEO, started the agency in 2000 for a bank holding company, after serving a brief stint at a captive insurer. After developing and running the agency for five years, he purchased the agency outright and changed the name to Rollo Insurance Group. This truly family-based agency is celebrating its 25th anniversary this year, in fact.

B.J. and Jason Rollo have been married over 30 years.
Above: Jason Rollo with his sons Jackson (President) and Josiah (Director of Marketing) in his home library

“Jackson … had the natural ability to take what I had built and grow it without sacrificing our commitment in continuing to feel like a mom-and-pop agency in each local community in which we do business … .”

—Jason Rollo

Founder and CEO

Above: Jackson in his office

“When we acquire an agency or open an office, we make certain that there’s a proper fit and that it is staffed by people who share our values. Everywhere we have a location, we believe that our reputation is on the line.”

—Jackson Rollo

President

Early on, Jason quickly found that doing all the jobs at the agency spread his talents too thin, so he asked his wife, B.J. (Bobbi Jan), to come onboard and to oversee the accounting, and she agreed. Although B.J. has always put being a mom first, she served as the chief financial officer until last year, managing the financial operations as the agency grew from a few people at one location to a multi-state, multi-million-dollar enterprise.

She recently handed the CFO reins over to John Hall, an actuarial sciences major from Texas A&M. B.J. continues to work at the agency on the M&A side and is co-owner along with Jason, her husband of 30 years.

Other incredible leaders and friends have been involved in this “family” endeavor for many years, including Kristin Baker, Beverly Moore, Justin Gaidusek, Michael Light, Daniel Horn, Ashley Lucas, and Josiah Rollo (Jason and B.J.’s youngest son, who is also an A&M grad, and quickly emerging in the agency as the current director of marketing), along with many others. Even Jason’s two daughters-in-law (Kate and Nikki) left their imprint, before focusing their efforts at home on the next generation of Rollo’s.

Above: Jason Rollo and Kristin Baker, Chief Risk Officer, stand in front of city maps representing the agency’s office locations.

Further, Jason and B.J. have two daughters who are currently in high school (Jenna and Julia) and who will undoubtedly exert their influence, as well. As Jason would put it, “Many great people have helped build this fantastic agency. Others may say it, but with us, we live it. We truly strive to be one big family.” 

As Jason unashamedly says, his belief in “God, family, and country serve as the underpinning for my life and business.” He plainly states, “Our integrity is not for sale.” Rollo Insurance strives to make everything they do in business reflect what is emphasized in their first rule, namely, “God is good. You should be too.”

The agency conference room displays The Rollo Rules and the agency slogan of “God, Family and Country.” From left: John Hall, Chief Financial Officer; Kristin Baker; Josiah Rollo; Jason Rollo; Jackson Rollo; Keith Lane, Chief Strategy and Talent Officer; Daniel Horn, Chief Technology Officer; and Cody Damron, Chief Operating Officer

Jason notes, “We are committed to always doing the right thing. That’s how we started out and that’s how we intend to continue to do business as we grow. Others grow with private equity and shareholder driven commoditization. Not us! We’re different and we believe that difference is real.”

Next generation

In 2019, Jason and B.J.’s oldest son Jackson, joined the agency as a producer while still at Texas A&M University, where he graduated magna cum laude in 2019. I guess his job didn’t interfere with his studies, nor did his studies interfere with his effectiveness as a producer. He earned the “Top Producer of 2019” designation in the agency. He later became director of sales and in January of 2022 he was named agency president. Working together, Jason and Jackson lead the agency.

Keith points out that “Jackson did not get handed the position; he earned it. I had a front-row seat and saw how diligently Jackson worked to earn not just his parent’s approval but the respect of the entire organization.

“There was a synergy there that proved propitious for the entire agency,” Keith continues. “Jason and Jackson have complementary talents that have helped us accelerate into becoming an agency with more than 65 local offices in six states and around 275 teammates working within the Rollo Insurance family.”

The breakthrough

Jason says, “Both Jackson and I have tremendous drive. But we’re different, and that’s good. We had a breakthrough when Jackson started as a producer. He had planned to go to law school after finishing up at A&M, but we both saw what he brought to the table, and that ultimately became the reason for his becoming president. My natural talent is more entrepreneurial.

Clockwise from top left: Trayton South, Account Executive; Natalie Cramblet, Account Manager; Logan Reeh, Accounting Specialist; and Ariel Hilton, Executive Assistant

“About the time Jackson started, I had reached my original goal with the agency. Jackson, who is more talented at scaling the organization, had the natural ability to take what I had built and grow it without sacrificing our commitment in continuing to feel like a mom-and-pop agency in each local community in which we do business.

“From his initial involvement, Jackson has often helped us take advantage of the efficiencies of automation, and other innovative techniques, including the importance of promoting our one-of-a-kind culture,” Jason adds. “In short, Jackson and I are a great blend of ‘old school’ and ‘new school,’ but with the same values.”

“We had to retool to make the next step,” Jackson remembers. “We were around 12 offices with 60 people when I came on board. Much had been done to lay the foundation, but blending old and new was extremely important.

“The key,” he says, “was to find or build technology that allowed us to spend more time with clients; the technology took care of the back office and repetitive functions involved in writing insurance that often interfered with our most important function: to build trusted relationships. We wanted to continue to be the agency that takes care of people.”

Jackson adds, “Everyone else seems to be very focused right now on building a specific niche. But these niches are often built around an industry or area itself, for instance in oil and gas or in construction. We decided to become experts in people, first. People—the right people—that is our niche. We feel that with the right people in place, we can then focus our efforts on certain areas. But first and foremost, the right people are what it’s all about.”

Building the culture

As the agency grew from one office to more than 65 in number, the need to present cogent rules that exemplified its adherence to the core beliefs of “God, Family, and Country,” became essential. These thoughts became the 12 Rollo Rules that now serve as guideposts for how the agency’s team operates.

“Each member of the Rollo team strives to exhibit these attitudes, and we recognize and reward our people for living them out,” Jackson points out.

As mentioned earlier, the first rule is: God is good. You should be too.

The other 11 are:

  1. Every person has a story. Every story matters. Tell yours and ask for theirs.
  2. Relationships ALWAYS matter.
  3. Perfection is impossible—Dream it. Chase it.
  4. The answer is Never: “Because we have always done it this way.”
  5. People + Purpose = Profit.
  6. Don’t be the problem. Fix the problem.
  7. Be Proactive. Be Diligent. Be Trustworthy.
  8. No matter who, where, or when—our greatest impact is local. Focus local.
  9. No Participation trophies allowed; We’re here to WIN.
  10. Know 3: Your Client, Your Value, Your Product.
  11. Do Right—Period.
In 2025, the agency debuted its Real Family Business podcast, which shares the “lessons and blessings” of running a family business. 

“This is an agency that is not run by capital; being family owned and operated is a strategic advantage. … All our offices have a unity of purpose, to live out the Golden Rule and act the right way in everything we do.”

—Keith Lane

Chief Strategy and Talent Officer

Jason says: “These rules provide us with a foundational format when opening new offices anywhere in the country and help us find people that will reflect the values for which we strive. Whenever we acquire an agency or open a new office, these rules help us to live up to our goal of growing ‘one great location at a time,’ and this, of course, can only be done by bringing in fantastic people and treating them fairly, as we always do.” 

Jackson continues, “When we acquire an agency or open an office, we make certain that there’s a proper fit and that it is staffed by people who share our values. Everywhere we have a location, we believe that our reputation is on the line.

“As Dad says regularly, ‘our integrity is not for sale.’ And if that means that we must pass on an opportunity to buy an agency or open a new location because there’s not a value match, that’s not a problem. Even though we have lofty well-planned goals, ultimately, it’s about opening one great office at a time.”

Keith chimes in: “This is an agency that is not run by capital; being family owned and operated is a strategic advantage. When I talk about it, I often speak about the focus on family. I really see Rollo Insurance as an agency that is serving Gatorade in the desert because we’re so different. All our offices have a unity of purpose, to live out the Golden Rule and act the right way in everything we do.”

Act local

Jackson adds, “When I think about the future and where we plan to go, it always comes down to the need to be where we can provide the greatest impact–and that’s always local. So, our strategy is simple.

“We put offices in the local communities where our valued people live,” he adds. “And while we currently have 65 offices—and by the time this article comes out, we might have more—one thing is for sure: Regardless of how fast we plan to grow, we want each office to embrace the local community and to fully understand our commitment to always doing what’s right.

“We can’t live everywhere that we have an office,” Jackson acknowledges, “so we must be certain that we have the right people in place in each of those local offices who will become involved in developing trusted relationships and in supporting their local communities. We recognize our responsibility in making certain that happens.

“As an example,” he explains, “we have a company-wide volunteer initiative that encourages every person who works at Rollo Insurance to get out there and make a difference in their local community. Every employee can earn an extra paid day off every year if they do sixteen hours of volunteer work on their own. Through this effort we hope to create positive change and make a meaningful impact in the lives of people who live and work in the numerous communities in which we have offices.

“Nearly all the organizations we support through this effort are local and include organizations like the Brazos Valley Food Bank, the Teague Baseball Association, Salado High School PTO, Young Professionals of Aggieland, Hannah’s House by Origins (an addiction treatment center), Freestone County Fair, Down Syndrome Association of Brazos Valley, and Beds of Hope, to name only a few,” Jackson concludes.

Rough Notes is proud to recognize Rollo Insurance Group as our agency of the month. Their commitment to acting locally provides yet another reason why the independent agency system continues to be the most successful in the industry. It offers each member the opportunity to paraphrase Frank Sinatra, to do it their way. This is certainly the case with Rollo.

rolloinsurance.com

The author

Dennis Pillsbury is a Virginia-based freelance insurance writer.

Tags: Agency of the MonthinsuranceRollo Insurance Group
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