Caroline Dennis | Founder and Executive Director | NuJourney Foundation
Caroline Dennis is a dedicated leader, entrepreneur, and financial educator with a passion for empowering communities. Originally from Florida, she began her collegiate journey at Howard University and later earned her Master’s in Project Management from Walden University. Over the years, she has built a remarkable career in finance, business, and nonprofit leadership, shaping the financial landscape for individuals and communities alike. At EliteX, we are proud to have Caroline Dennis as part of the edition: 10 Elite Women in Business, 2025.
As the President & CEO of Chayil Financial Group, a holding company with multiple subsidiaries, including Chayil Consulting, she has played a pivotal role in providing financial solutions and strategies. Additionally, she serves as an Assistant Vice President at a leading financial services firm, further solidifying her expertise in the industry. Beyond her corporate and entrepreneurial roles, she is the Founder and Executive Director of the NuJourney Foundation, a nonprofit organization dedicated to providing financial and entrepreneurial education to underserved communities. Her work has been instrumental in bridging financial literacy gaps and fostering economic growth.
“Never walk in someone else’s shoes. Get your own damn shoes to make sure they fit.”
Caroline is also an accomplished author, having written two books: “Take the Journey: The Powerful Steps to Owning Your Story,” an award-winning book, and “Who Am I Financially Speaking,” her most recent publication, both available on Amazon. Through her writing, she provides insightful guidance on personal growth and financial well-being, helping readers navigate their financial journeys with confidence and clarity. Her decision to start her own business stemmed from a desire to take control of her growth and influence. She recognized the limitations of the corporate environment and sought the freedom to align her work with her values. By establishing her business and nonprofit, she created a platform where she could drive meaningful change and impact lives on her own terms. It was not just about pursuing a career but about building something authentic and sustainable.
In the early stages of her career, Caroline faced the challenge of identifying the right spaces to grow and thrive. Initially, she believed that success required saying yes to every opportunity and following all advice. However, she quickly realized that this approach was exhausting and unsustainable. Through reflection and strategic adjustments, she learned the importance of intentionality, purpose, and clarity. These principles have guided her journey and continue to shape her success today.
For Caroline, leadership is rooted in service, vision, influence, and grace. She believes that leadership is not about the individual but about ensuring that everyone involved in the mission feels valued and empowered. By fostering a culture of inclusion and appreciation, she enables her team to perform at their best. She also emphasizes the importance of grace—acknowledging contributions, supporting growth, and creating an environment where everyone can thrive.
While she does not pinpoint a single ‘shining moment’ in her career, she distinguishes between acknowledgment and recognition. Acknowledgment is fleeting, whereas recognition signifies a deeper understanding and connection to her mission. She considers it a true affirmation when people not only notice her work but genuinely recognize the purpose behind it.
“Leadership is not about the individual but about ensuring that everyone involved in the mission feels valued and empowered.”
Authenticity is a core value for Caroline. She firmly believes that staying true to oneself is essential for building trust and credibility. Self-awareness, confidence, and a commitment to genuine interactions set individuals apart in any industry. Customers and clients can quickly discern authenticity, making it a critical factor in business success. Having entered the financial industry just before COVID, she witnessed the rise of social media as a business tool. Visibility became a crucial factor for success, and although it was initially outside her comfort zone, she embraced it as an essential strategy. To further her reach and impact, she launched a podcast, providing a direct platform to engage with her audience and deliver valuable insights.
Caroline understands that financial education is evolving. Simply discussing budgets and investments is no longer enough; effective communication and engagement are key. She actively explores innovative ways to present financial knowledge, leveraging new platforms and interactive tools to enhance learning and bridge the gap between knowledge and action.
Continuous learning is a priority for Caroline. She stays ahead by maintaining curiosity and seeking knowledge beyond her industry. Attending workshops in various fields allows her to integrate fresh perspectives into her work. While keeping up with trends is important, she believes authenticity is the ultimate differentiator, ensuring relevance and long-term success. When advising others, she encourages them not to follow in her exact footsteps but to use her journey as inspiration to find their own path. She highlights the importance of discovering one’s own space—the place that resonates deeply. She recalls a powerful quote: “Never walk in someone else’s shoes. Get your own damn shoes to make sure they fit.” This philosophy underscores her belief in individuality and self-discovery.
Caroline is deeply passionate about empowering women. She believes that women must first recognize their own value and appreciate the strengths of others. Confidence and collaboration are essential, as women have the power to shape future generations and uplift their communities. By supporting each other instead of competing, women can redefine leadership and create lasting change. Her greatest inspiration comes from the people who have influenced her journey. Her parents instilled in her a strong foundation of perseverance and ambition. Her niece and nephews inspire her daily with their intelligence and authenticity, keeping her grounded and motivated. Additionally, her community challenges her to remain true to her mission, providing continuous encouragement and accountability.
Balancing work and personal life is an ongoing struggle for Caroline. However, she prioritizes being fully present in the moments that matter, whether in her professional or personal life. She believes that presence and intentionality are the keys to creating meaningful experiences and lasting memories. While she has accomplished much, she does not believe she has reached her greatest achievement yet. She views her journey as a continuous process of learning, growth, and contribution. With so much more to do, she remains committed to making a lasting impact.
“Authenticity is the ultimate differentiator, ensuring relevance and long-term success.”
The legacy she wishes to leave for women in business is one of empowerment and collaboration. She envisions a future where women confidently set their own boundaries, normalize financial conversations, and support each other’s success. She hopes to create a blueprint for future generations, fostering a culture where women not only thrive individually but uplift others as they climb.
Above all, Caroline Dennis is a testament to what is possible with determination, authenticity, and a commitment to service. She is dedicated to changing the narrative around financial health, building strong individuals, sustainable businesses, and thriving communities. And, of course, she proudly embraces her role as the Best Auntie Ever—a title she holds dear alongside her many accomplishments.
