Cynthia Whitfield-Story has a passion for developing leaders, creating and aligning business and talent strategies, and cultivating diverse and inclusive teams and organizational cultures.
For more than 30 years, Cynthia has been dedicated to coaching, supporting, and mentoring leaders. She believes that authenticity is the key to strong, effective leadership. Paired with her ability to integrate strategy development with a people-first approach, these components drive unique solutions to challenges that establish accountability and achieve business results.
Cynthia retired from Allstate Insurance Company as the field Senior Vice President of the Southern Region after holding various leadership roles in Operations, Accounting, Finance, Risk Management, and Product Operations. In her role as Vice President of the Southern Region, she was accountable for business results for the states of Tennessee, Kentucky, Mississippi, Arkansas and Louisiana, including all profit and loss results as well as managing a revenue stream of nearly $2 billion and a team of nearly 2,500 leaders and team members.
She is certified in Hogan Assessments, as well as in Marshall Goldsmith’s top-ranked Stakeholder-Centered Coaching® methodology—recognized globally for its effectiveness with senior leaders—Cynthia helps executives achieve measurable, behavior-based growth through structured feedback and accountability.
She strongly believes in giving back to the community and was board chair of the Nashville YWCA 2022-2023 and a major sponsor for the AMEND Together program. She serves on the Girls Inc. Advisory committee of the YWCA. She served as chair of Big Brothers Big Sisters of Middle Tennessee in 2019. She serves on the board of Dream Big Fund Trust for BBBS and is a member of Leadership Nashville and Nashville Chamber of Commerce. She served on the Advancing Women of Nashville board of directors and is now on the advisory committee and is the chair of FiftyForward. She also serves as a board member of Nashville State Community College and The Store food bank.
Cynthia has been widely recognized for her outstanding volunteerism and community leadership. She was named one of Nashville Business Journal’s Women of Influence and received the Macdonald-Negri Service Award from AMEND Together and the YWCA in 2018. Her commitment to youth mentorship earned her the Jimmy Webb Volunteer Leadership Award from Big Brothers Big Sisters. Most recently, she was honored as a 2024 ATHENA International Award recipient and inducted into the YWCA Nashville & Middle Tennessee’s Academy for Women of Achievement in 2025.
She is frequently invited to speak at large events, where she inspires and teaches others through her engaging presence and leadership insights.
A New Jersey native, Cynthia earned a degree in business administration from Rutgers University and a Master’s in Management from Indiana Wesleyan University.
