Ashley Winters represents the next generation of the Winters family and the continuing legacy of Sir Jason Winters International.

Ashley’s journey with the company began when she was just 16 years old. What started as a young girl learning the family business grew into more than two decades of hands-on experience, responsibility, and dedication. For more than 21 years, Ashley has worked her way through the business, learning the company from the ground up and gaining an understanding of the people, products, customers, and relationships that have made Sir Jason Winters International what it is today.

She did not simply step into a position because she was part of the Winters family. She grew into it.

Education & Experience

Ashley’s education has complemented her extensive experience in the family business. She holds a degree in psychology and a Bachelor of Science in Business Administration, graduating Magna Cum Laude.

Her background in psychology gives her an understanding of people, communication, compassion, and the importance of helping others. Her education in business administration provided her with the business knowledge and foundation necessary to help lead and develop an international family-owned company.

Combined with more than two decades of practical experience, Ashley brings a unique perspective to her role—one that combines education, business knowledge, personal experience, and a genuine understanding of people.

Over the years, Ashley has been involved in virtually every aspect of the business. She has learned the importance of customer service, product quality, international relationships, e-commerce, operations, marketing, and distribution. Her experience has given her a unique perspective: she understands both the history of the company and the realities of running a modern international family business.

Today, Ashley serves as Chief Operating Officer of Sir Jason Winters International, where she plays an important role in the day-to-day operation and continued development of the company. Her responsibilities include overseeing operations, e-commerce, product development, customer relationships, and international distribution.

Her relationship with the business is also deeply personal. Ashley grew up surrounded by the people, conversations, challenges, and experiences that come with being part of a family company. She witnessed firsthand the commitment required to maintain a business built by previous generations, while also learning that a family legacy cannot simply be preserved—it must be earned again by each generation.

That has shaped the way Ashley approaches her work.

She believes that the responsibility of the next generation is not simply to protect what was handed down to them, but to understand it, respect it, improve where possible, and make sure it remains meaningful for the future.

Ashley also understands the unique demands of balancing family, motherhood, and a career. As a mother herself, she brings that perspective into her work and appreciates the importance of creating a life in which family, personal responsibility, and professional commitment can coexist.

Her connection to Sir Jason Winters International goes far beyond a job title. More than two decades in the company have given Ashley a deep appreciation for the relationships that have been built around the Winters name and the trust that customers have placed in the company over generations.

She is proud of where the company came from—but she is equally focused on where it is going.

Ashley Winters is not simply carrying on a family business. She is helping shape its next chapter.