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Brian Lillis

Brian Lillis: Upholding a Legacy of Service and Community in the World of Insurance

A Story of Community, Continuity, and Commitment in a Changing World!

In a rapidly changing world where uncertainty seems to be the only constant, insurance as a beacon of trust, continuity, and community. It’s a world where promises are kept, where the unexpected is prepared for, and where the collective strength of a community is harnessed to protect against life’s uncertainties.

In this world where trust, continuity, and community are paramount, Brian Lillis stands as a living testament to a legacy that spans generations. As the Chief Operating Officer of Ryan Specialty Underwriting Managers (RSUM), a division of Ryan Specialty, his journey is intertwined with the enduring history of Lillis Insurance Agency, a family institution in Williamsburg, Iowa.

Lillis Insurance Agency’s story is one of deep roots and enduring presence in the heart of Williamsburg, Iowa. It was founded by Brian’s grandfather in 1937, setting in motion a legacy that has thrived for nearly a century. From his grandfather’s founding vision to his grandmother’s stewardship and other family members who continue to carry its legacy forward as a beacon of trust and reliability within the community.

Brian’s journey into the world of insurance was greatly influenced by his father who joined Principal Financial as an actuarial student, following in his father’s footsteps and embracing the family tradition. Over the years, his dedication and expertise led him to hold various senior positions, specializing in actuarial work, risk management, and product pricing. His journey culminated in the esteemed role of Chief Financial Officer, a position he held with distinction for a decade before retiring.

Brian’s father was more than a professional mentor; he was a role model who shaped Brian’s values and principles from a young age. Brian’s life journey reflects the enduring influence of his father’s guidance, wisdom, and commitment to excellence.

Join us as we explore his unwavering dedication to service, his family’s enduring legacy, and his pivotal role in the ever-evolving world of insurance!

Building a Culture of Excellence

Brian says Ryan Specialty’s success story since inception is about the culture that Pat Ryan and Tim Turner created by surrounding themselves with talented, like-minded, hardworking, and extremely driven individuals. The competitive environment compels the employees to bring it every day to win.

From FP&A Manager to COO

When Brian initially joined Ryan Specialty Underwriting Managers in 2013, he stepped into the role of Manager of Financial Planning and Analysis (FP&A), a position that was newly established. His primary responsibility was to build and develop the FP&A function across the RSUM platform. This task was no small feat, as it required creating an essential analytical and data-driven component within the company.

Brian was fortunate to work under the leadership of Miles Wuller, President and CEO of RSUM, and others within Ryan Specialty, where executives highly value analytical thinking and data-driven approaches. This unique environment meant that Brian’s role within RSUM was more expansive and challenging compared to his previous positions in other organizations.

Throughout his career at RSUM, Brian has embraced various roles and responsibilities, driven by his ability to tackle strategic, financial, operational, and data-related challenges. Whenever he is presented with a task aimed at benefiting the company, his response is consistently confident: “Yes, I can do that.” Working within a flat organizational structure, especially during the organization’s growth phase, provided Brian with opportunities to contribute to all facets of the business. This exposure and his unwavering commitment to RSUM has played a pivotal role in propelling his career faster than he initially anticipated.

Today, as the Chief Operating Officer (COO), Brian still acknowledges the fundamental importance of his initial role as the FP&A Manager. He continues to carry out responsibilities associated with that position, fully aware of the profound impact it has on the organization. Brian has instilled this mindset in his current team, emphasizing that every aspect of their job prepares them for future opportunities and personal growth.

Lessons from Challenges and Successes

During Brian’s impressive decade-long journey at Ryan Specialty, he has witnessed the company’s ascent to a prominent position as a market leader in the insurance industry. This tenure has provided him with invaluable insights and knowledge that can only be acquired through firsthand experiences. While there have been numerous triumphant ventures, what Brian truly treasures are the lessons extracted from the challenges that didn’t yield immediate results.

Faced with these obstacles, Brian and his team engaged in consistent brainstorming sessions, endeavoring to conceive innovative solutions to tackle complex problems. These experiences significantly deepened their expertise in the realm of insurance and fortified their capabilities.

However, among the myriad experiences, the most pivotal in terms of operations, technology, and finance was the successful acquisitions of Managing General Underwriters (MGUs) that became part of the RSUM family. These endeavors encompassed multifaceted aspects, including the negotiation process, understanding the mutual commitments from both parties, embracing the success of the MGUs, integrating the acquisition into the existing framework, and more. Remarkably, these were accomplished without disrupting the growth trajectory of either entity allowing MGU to maintain and enhance their competitive advantage. Simultaneously, the acquisitions achieved synergies and upheld a steadfast commitment to the long-term strategy and continue to improve their return on investment.

Ongoing Commitment to Data & Analytics

From its very inception, Ryan Specialty has been steadfastly dedicated to Data & Analytics. This unwavering commitment has driven the company to continually refine its data strategy, recognizing the immense potential it holds not only for its own operations but also for the benefit of its clients.

The utilization of data has already proven to be a formidable asset for the firm, yielding notable positive outcomes. However, the journey is far from over. The organization remains acutely aware of the vast reservoir of data available, and it acknowledges the substantial room for growth and enhancement and appropriately staffing to harness this.

Collaborative Culture and Ongoing Talent Search

Ryan Specialty thrives on teamwork and a flat organizational structure that encourages open communication. This setup allows for the quick consideration of ideas, fostering discussions and debates across the organization. When consensus is reached, ideas can be put into action promptly, promoting the real-time exchange of information and innovative concepts throughout the company.

These ideas come from the strategic thought leadership of the MGUs CEOs and executive leadership, who engage daily with the market, brokers, competitors, and key Ryan Specialty figures. They play a vital role in driving innovation.

To stay competitive, RSUM is always on the lookout for talented individuals in various roles to enhance their value chain. They consistently conduct interviews to attract top talent, most recently during the uncertain times in the insurtech industry. This infusion of talent adds a dynamic dimension to their core IT teams, incorporating valuable lessons from the past and capitalizing on insurtech experience to ensure future success.

Strategic Planning and Commitment

Over the past year and a half, Ryan Specialty has been diligently managing its operations while simultaneously pursuing ambitious objectives. During this time, the firm has developed a comprehensive IT roadmap, refined its operating model, and elevated its data strategy, all in preparation for the future. Understanding that change is a constant in their industry, Ryan Specialty has dedicated substantial efforts to ensure they are well-prepared for whatever challenges may come their way.

His forward-thinking approach has sometimes required difficult decisions, including the prioritization of larger strategic initiatives over smaller isolated advancements. Looking ahead, their primary focus is on fulfilling commitments made to the MGUs executive leadership. These MGUs have faced and continue to confront significant challenges, and Ryan Specialty is committed to providing unwavering support throughout their journey.

Moreover, the firm places great importance on demonstrating a substantial return on its investments, generating profits on behalf of its carrier partners and will take responsibility for validating this through various commitments. While progress is assessed quarterly, it’s essential to recognize that the level of investment in these initiatives is truly remarkable. Ryan Specialty’s dedication to strategic planning and commitment to its goals shape a promising path forward.

Cultivating Future Leaders

While advising aspiring entrepreneurs, Brian emphasizes the importance of self-development for aspiring leaders. He believes that organizations should invest in developing their staff and future leaders, but individuals should not rely solely on the organization for their development and career growth. Aspiring leaders must take the initiative and be accountable for continuously improving themselves, learning from mistakes, failures, and successes, with the aim of increasing their value to the organization. Understanding and embracing the organization’s culture, which is often shaped by the executives leading the strategy, is crucial for aspiring leaders and if not aligned there are other opportunities elsewhere, where they may thrive.

In his experience with RSUM over the past five years, Brian has observed that hiring talented individuals alone is not sufficient. A motivated work ethic, a drive for constant improvement, a competitive nature, and an entrepreneurial spirit are also necessary for success at the company.


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