Meet our

Black Sheep Team

Jana Caswell


Leveraging 30 years of Human Resources leadership and independent consulting, Jana brings her experience in partnering with organizations of all sizes across a multitude of industries to the Black Sheep team; helping unleash the value of their human capital. With experience as a corporate executive and consultant, her expertise in leadership development, diversity equity and inclusion, employee relations, labor relations, dispute resolution, executive coaching, and training and development help ensure that employees work as strategic business partners, positively contributing to an organization’s culture and bottom line.
Jana Caswell
Jana’s corporate career includes Human Resources leadership with Hyatt Hotels and Resorts and Darden Restaurants, parent company of The Olive Garden, Longhorn Steakhouse, Capital Grille and other leading restaurant brands. As the Vice President of Strategic Employment Practices for Darden Restaurants, she was responsible for enterprise-wide, fair and legally compliant policies and practices for the organization’s 200,000 employees across the United States and Canada. As a consultant, Jana has helped develop leaders and build HR infrastructure across multiple organizations and industries, including Petco, Advent Health, United Rentals, Boeing, Moen, and Duke University Health.

In addition to holding a Bachelor of Arts degree in International Relations from American University in Washington, DC, and certificates in Executive Coaching and Diversity and Inclusion from ATD and Cornell University, Jana is also fluent in Spanish and is a licensed private pilot. She has served on a variety of non-profit boards and remains an active volunteer with animal welfare organizations and the University of Central Florida’s Small Business Development Center (SBDC).




Lives Changed

People who trust us.

Black Sheep is known by the company we keep. And we have coached and consulted
the best-of-the-best in business, government, health care, and non-profit.