Her Story
About McKenna
McKenna Bailey serves as Director of Client Experience at Imagine360, where she provides strategic leadership focused on client relationships, service, and retention. With eight years of experience in the health insurance industry, she has developed a strong understanding of the employee benefits landscape and the importance of creating meaningful, long-term partnerships with clients. In her current role, Bailey leads a team of six professionals who each manage full client portfolios, while she personally oversees national accounts and works closely with clients to ensure their needs are understood and effectively addressed. Her responsibilities include supporting client success, strengthening relationships, and helping employers recognize the value of Imagine360’s specialized healthcare solutions.
Bailey began her career in the insurance industry in 2018 at a brokerage where her mother served as an executive vice president. The experience gave her an early introduction to the industry and provided access to valuable mentorship and guidance. At the same time, Bailey was determined to establish her own professional identity and build a career based on her own knowledge and accomplishments. She later joined Imagine360 in 2021 as a Relationship Manager and steadily advanced through positions of increasing responsibility, becoming Senior Relationship Manager, Senior Manager of Client Experience, and ultimately Director of Client Experience. Throughout this progression, she has continued to expand her expertise in client service, benefits, compliance, and relationship management. Bailey earned a Bachelor of Business Administration from the University of Cincinnati and holds a Life and Health Insurance License.
Bailey credits much of her success to maintaining a mindset of continuous learning and being a dedicated student of the industry. Early in her career, she made a point of reading extensively, studying industry materials, and gaining hands-on experience in areas such as compliance, even when those responsibilities were not necessarily the most appealing. She believes that setting ambitious goals is important, while also recognizing the value of being realistic and patient with the timeline for achieving them. One of the opportunities she sees in the industry is educating employers and clients about Imagine360’s niche healthcare solutions, as greater understanding often leads to stronger engagement and partnerships. Beyond her professional accomplishments, Bailey places a high value on family and work-life balance. She appreciates working for a family-oriented organization that provides the flexibility to attend her children’s school events and remain present for important milestones. Spending time with her husband, three children, and extended family remains an important part of the life she works to build alongside her professional career.
Her Interview
Ten minutes with McKenna
01What do you attribute your success to?
I attribute my success to being a lifelong student of the industry, particularly early in my career when I made a deliberate effort to learn everything I could. I read extensively, asked questions, and was willing to get hands-on experience in every aspect of the business, including compliance, an area that many people may not enjoy. By immersing myself in the work, understanding the details, and continuously expanding my knowledge, I developed a strong foundation that has continued to guide my professional growth.
02What’s the best career advice you’ve ever received?
The best career advice I have received has come through exceptional mentorship and the willingness to learn from those around me. I began my career at my mother’s brokerage, where I was fortunate to benefit from her guidance, expertise, and firsthand knowledge of the industry. Later, at Imagine360, I had the opportunity to work with Chris H., a distinguished female leader who provided valuable mentorship and support as I continued to grow professionally. These experiences taught me the importance of seeking out great mentors, learning from their experiences, and applying those lessons to my own career.
03What advice would you give to young women entering your industry?
My advice to young women entering the industry is to never be afraid to set big goals and believe in what you are capable of achieving. At the same time, it is important to be realistic about the timeline and understand that meaningful career growth takes time. Be patient with yourself, stay focused on your goals, and recognize that success is a journey built through consistent effort, learning, and perseverance.
04What are the biggest challenges or opportunities in your field right now?
One of the biggest challenges in my field right now is educating employers and clients about what our company truly does and the value of our solutions. Because we operate in a niche space, there can be a lack of awareness or understanding of how we can support employers. Once clients understand our approach and the solutions we provide, building trust and moving forward becomes much easier. For me, the greatest opportunity is continuing to educate the market, create awareness, and help employers recognize the value we bring.
05What values are most important to you in your work and personal life?
The values that are most important to me in both my work and personal life center around family and maintaining a healthy balance. I am grateful to work for a company that is very family-oriented and gives me the flexibility to be present for important moments, whether that means attending my children’s school events or simply spending quality time together. Being able to prioritize time with my husband, my three children, and our extended families is incredibly meaningful to me, and I value having a career that allows me to be successful professionally while still being present for the people who matter most.
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