Women To Watch 2025 honoree Caroline Dennis

Caroline Dennis is a powerhouse in financial empowerment, with over 20 years of experience in financial services and a mission-driven approach to building financially healthy individuals, families, and communities. As the Founder and Executive Director of NuJourney Foundation, a nonprofit dedicated to transforming underserved communities through financial and entrepreneurial education, she is rebranding what financial literacy means—shifting the conversation from information-based to value-based.

A visionary leader, Caroline is also the President and CEO of Chayil Financial Group, a dynamic holding company. She also serves at the helm of President/CEO of Chayil Consulting, LLC and Manager Member of Harvest Partners Investment Group. She serves as the AVP at a national financial services firm. She is the creator of a unique "financial personalities" model, helping people understand their financial behaviors and motivators to drive real, lasting financial change.

An award-winning author of multiple books, including Who Am I, Financial Speaking and Take the Journey: The Powerful Steps of Owning Your Story. Caroline is a powerful storyteller who uses her words to inspire action. She holds an undergraduate degree in Finance and a Master’s Degree in Business Administration/Project Management.

Caroline’s work is deeply rooted in community, collaboration, and impact. Whether speaking on national stages, mentoring the next generation of leaders, or forging new partnerships, she believes that “the mission is too great to go at it alone.” Her leadership has earned her a place among the “Top Leader of 2024” and “Top 10 Elite Businesswomen in 2025,” and her influence continues to grow across faith-based, corporate, and grassroots spaces alike. Caroline touts her guiding principle of Grace as her compass through life.

When she’s not changing lives, Caroline loves to travel, read books, surround herself with good energy, and proudly holds the title of “The Best Auntie Ever.”