Perspectives

May 30, 2025

My career, my story: Ryan Winter

My journey at Lockton Affinity has been one of growth, innovation, and collaboration. From my early days as a rater in the Operations department to my current role overseeing complex programs, I've had the privilege of working with talented colleagues and contributing to meaningful projects. Lockton Affinity stands out for its commitment to customized solutions, exceptional service, and a culture that empowers associates to make a real impact. Here, I share my experiences, insights, and the moments that have defined my career at Lockton Affinity.

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After graduating from Kansas State, I was eager to begin my career with a company that valued growth and innovation. Lockton was the first company that came to mind in Kansas City, and it ended up being the only place I applied. Following a phone interview and an in-person meeting, I was fortunate to be offered a position. I started my career at Lockton as a rater in the Operations department, supporting program business across multiple carriers, rate systems, and lines of coverage. I was later promoted to team lead, where I managed a small team focused on delegated program business. In that role, I concentrated on driving process improvements and operational efficiencies to help streamline team workflows and enhance overall performance.

After several years, I transitioned into leading our backroom operations team, responsible for issuing thousands of policies and certificates for PEO workers’ compensation programs and a large fleet auto program. This role allowed me to take a more strategic approach—identifying opportunities to optimize systems and implement solutions that delivered measurable time and cost savings. During this time, I was promoted to Assistant Vice President.

Two years ago, I made a significant shift to the client side. After over a decade in process-driven roles, I now oversee the success of several complex programs, working closely with carrier and program partners while ensuring our internal teams deliver the high level of service Lockton is known for. Though I no longer have direct reports, I collaborate across departments and remain actively engaged in a wide variety of programs, which continues to challenge and inspire me.

As I mentioned, Lockton Affinity is the only organization I’ve worked for in my professional career, and throughout my time here, I’ve had the opportunity to collaborate with a wide range of brokers and carriers. That broader exposure has only reinforced how unique and special this place truly is. What sets Lockton Affinity apart is our ability to design highly customized insurance programs tailored to meet the specific needs of our clients—no matter how niche or complex. We bring the strength of human talent backed by smart technology, allowing us to offer solutions that are both personal and efficient. Paired with the exceptional service we deliver, it’s a combination that’s genuinely hard to find elsewhere. There’s a deep sense of pride in the work we do and a culture of collaboration and innovation that makes Lockton Affinity more than just a workplace—it’s a place where people are empowered to make an impact.

One of the things I value most about Lockton Affinity is the freedom I’ve been given to explore and improve our processes—always with the goal of creating a more efficient, positive experience for our clients. There’s a strong culture here of empowering associates to lean into their strengths and apply them to both new and existing programs, and that’s what truly fuels innovation at Affinity. I’ve often been challenged to find fast, effective ways to rate new programs, and each time, I’ve been trusted to build and implement the solution from the ground up.

Over a year ago, our President approached me with an opportunity that was not only a win for our business but also aligned us with an organization doing meaningful work in the world. As the cliché goes, the initial workflow was figuratively sketched on the back of a napkin. From there, and in close collaboration with one of our valued carrier partners, we brought a highly efficient technology solution to life. For me, it was the perfect blend of process development, problem-solving, and contributing to something bigger than ourselves. That experience—where innovation, purpose, and partnership came together—is what I’d call my Lockton Moment.

The culture at Lockton Affinity is all about balancing hard work with enjoying the journey. We work hard to tackle unique and challenging problems, but we also know how to have fun along the way. There's a real encouragement to be innovative, constantly looking for new solutions to help our clients succeed. While we work with small businesses, the impact we make is big, and the challenges we face are anything but ordinary. It’s a place where creativity and collaboration thrive, and everyone is motivated to push the envelope—making it a place where work feels rewarding and impactful.

Ryan Winter

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At Lockton, we believe you deserve a career that’s just as exceptional as you are. If this sounds like you, just imagine what we could do together.

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