ASHLEY L. FREEMAN

Vice Chairwoman

About Ashley L. Freeman

Ashley L. Freeman serves as Vice Chairwoman of Ashley & Roy Freeman Family Office LLC. Working alongside her husband, Roy, she co-steers the firm’s strategic vision and expansion across a diverse portfolio of subsidiaries and investments.

Ashley L. Freeman (2024)

Known for her analytical rigor and collaborative leadership, she ensures that each strategic initiative aligns with the family office’s long-term objectives of efficiency and positive social impact. Her systems-thinking approach and military-wife discipline underpin the family office’s integrative and resilient growth strategy.

Ashley L. Freeman (2025)

Healthcare Technology Innovation

A nationally certified and state-licensed pharmacy technician since 2009, Ashley brings over 15 years of clinical and operational expertise to her role at PioneerRx—the highest-rated and most widely adopted independent pharmacy software provider in the United States.

Her deep understanding of pharmacy workflows, patient care, and regulatory compliance informs strategic decisions that drive innovation and excellence across the platform. She champions innovation in pharmacy workflow technology, enabling independent pharmacies to enhance patient care and streamline operations.

Ashley L. Freeman (2025)

Her experience at CVS and Precision Pharmacy further sharpened her operational expertise, from large-scale retail settings to specialized medication services.

This multifaceted background equips her to bridge the gap between frontline pharmacy practice and cutting-edge tech solutions.

Community and Educational Advocacy

Ashley has demonstrated steadfast commitment to local educational and extracurricular initiatives.

She served as Chairwoman of the Petal Band Boosters—a 501(c)(3) organization—for three years, during which she led fundraising efforts that generated over $150,000 in support of the Petal Band, along with personal donations and volunteering thousands of hours.

She currently holds the role of Treasurer for the Petal Speech & Debate Booster Club, overseeing financial stewardship and resource allocation for student enrichment.

Through these leadership positions, she empowers youth programs and fosters community pride.

Ashley L. Freeman and Roy W. Freeman Jr. (2025)

Philanthropic Vision

Ashley sits on the leadership team and board of the Ashley & Roy Freeman Foundation. She leverages her strategic acumen to direct resources toward education, community health initiatives, and programs that uplift underserved populations.

Her blend of high-level business stewardship, hands-on healthcare proficiency, and heartfelt philanthropic drive amplifies the foundation’s impact. Ashley continues to champion sustainable growth and meaningful community advancement through purposeful giving.

Ashley L. Freeman (2025)

With her unwavering dedication to innovation, community empowerment, and strategic vision, Ashley L. Freeman continues to build a lasting legacy—championing impactful solutions today while laying the groundwork for tomorrow’s successes.

Personal Life

Ashley lives in Petal with her husband, Roy. They have four sons.

Samuel J. Freeman, Jon T. Freeman, Trace W. Freeman, and Jeremiah K. Whitworth (2024)