Her Story
About Kylie
Kylie Fields, is a compliance and privacy leader who serves as the Compliance Manager and Privacy Officer at Shepherd Insurance in Indianapolis, Indiana. With a background that combines law, bioethics, healthcare regulation, and insurance compliance; Kylie specializes in translating complex regulatory requirements into practical strategies that help organizations manage risk and make informed decisions. She began her compliance career in 2019 after completing her graduate education and law degree, initially pursuing “cleanup compliance” work within a long-term acute care facility before transitioning to insurance, where she found her passion in proactive compliance—helping clients prevent regulatory challenges before they arise. Her expertise includes navigating requirements from federal agencies such as the Department of Labor, Internal Revenue Service, Department of Health and Human Services, and Centers for Medicare & Medicaid Services, as well as state and local regulations affecting employers across diverse industries. Kylie’s educational journey reflects her commitment to understanding the intersection of law, healthcare, and ethics. She earned a Master’s degree in Bioethics and Medical Humanities from the University of Louisville while completing her Juris Doctor at the Louis D. Brandeis School of Law. In her current role, she supports both internal teams and clients through compliance discovery calls, assessments, policy guidance, regulatory updates, and tailored solutions designed to address evolving legislation. Known for her ability to simplify complex legal concepts and communicate them effectively, Kylie focuses on creating compliance programs that are not only legally sound but also practical and meaningful for the people who rely on them. Kylie is also dedicated to professional leadership, having served on the Advisory Board for Women in Leadership at Valparaiso University and currently acting as President-Elect of the National Association of Benefit Insurance Professionals (NABIP) Indy Chapter. Driven by curiosity, continuous learning, and a desire to empower others, Kylie believes that knowledge is one of the most valuable tools a professional can develop. As a testament to her philosophy, Kylie visits the Capitol each February to meet with members of Congress to discuss upcoming legislation and its impact on our healthcare system at large. She attributes her success to her willingness to ask questions, embrace challenges, and continually seek opportunities to grow while helping others do the same. Beyond her professional responsibilities, she contributes to her community through volunteer efforts and leadership initiatives, including work with organizations that support children and families. As an emerging leader in legislation, compliance, and insurance, Kylie encourages the next generation of professionals to seek knowledge and not be afraid to tackle the big issues—because understanding complex problems and turning that knowledge into viable solutions creates lasting change.
Her Interview
Ten minutes with Kylie
01What do you attribute your success to?
I attribute my success to persistence and having a willingness to ask questions. In compliance, knowledge is one of the most valuable tools because regulations are constantly evolving, and staying informed is essential. I also credit my diverse professional experiences for helping me develop adaptability, strong communication skills, and the ability to understand and work with people from different backgrounds. Being able to empathize and communicate with others in various roles is key to cultivating successful relationships. Each experience has strengthened my work ethic, problem-solving abilities, and ability to navigate new challenges.
02What’s the best career advice you’ve ever received?
The best career advice I have received is to never stop asking questions and remain open to learning from others. Throughout my career, I have benefited from experienced professionals who helped me understand complex systems, different approaches, and a new style of thinking. I have learned that growth comes from being curious, seeking guidance, and recognizing that every person and experience can teach you something valuable.
03What advice would you give to young women entering your industry?
My advice to young women entering compliance is to get comfortable with the uncomfortable. Everyone starts at the beginning and not having all of the answers is okay. What matters is being willing to learn and become knowledgeable on whatever topic you are being tasked with understanding. Knowledge is your biggest attribute, and developing a strong understanding of your field will help you become an asset to your team, create opportunities for your clients, and make a meaningful impact on your legacy.
04What are the biggest challenges or opportunities in your field right now?
One of the biggest challenges and opportunities in compliance is navigating constantly changing regulations. As requirements continue to evolve, organizations need dedicated compliance professionals who can provide guidance, reduce risk, and help protect businesses from liability. I believe this creates an important opportunity for compliance professionals to serve as trusted partners who help organizations understand not only what the rules require, but why they matter.
05What values are most important to you in your work and personal life?
The values that guide me most are integrity, accountability, curiosity, and service. I believe compliance professionals have a responsibility to provide accurate guidance while helping organizations make informed decisions that align with their values and obligations. Outside of work, family is extremely important to me, and I strive to build a meaningful career while remaining present and engaged as a mother, wife, sister, and daughter.
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