Deidra Jackson

Deidra Jackson has served as a healthcare executive for the last 25 years leading product and business development efforts across national and regional payer organizations as well as digital health platforms. Her decades of experience developing healthcare resources revealed what she now sees in her own family—that sick and aging veterans are not the ones tracking appointments, managing medications, or translating clinical instructions into daily living. It is their caregivers.  

Deidra’s father Leroy Avery, Jr. served four years on active duty in the U.S. Air Force. As an Airman, he served with the Military Police during the Vietnam War. Leroy was exposed to Agent Orange, which has triggered or complicated a list of debilitating health conditions, including diabetes, heart failure, kidney failure, gastroparesis, and recurring blood clots.  

Leroy’s dependence on his daughter has grown over the years. Deidra’s role as a caregiver began with smaller, episodic acts of care before evolving into daily oversight of his basic needs and safety. Deidra managed his care during extended hospital stays and attempts at living alone, before moving him into an independent living facility. She soon realized that he needed more support and care, so she moved him into her family home.  

Before becoming a Dole Caregiver Fellow, Deidra was already building connections between other veteran caregivers. She published a memoir and companion journal about her caregiving journey to bring awareness to the experience and assure her fellow caregivers that they are not alone. Deidra also speaks at events about her caregiving experience, including her keynote address at the Military Caregiver Breakfast at the 2025 Military World Expo.  

As she continues her advocacy, Deidra is eager to use her professional and personal experience to champion the idea of formalizing the role of the caregiver within healthcare delivery. She says, “When caregivers are recognized, supported, and integrated into care planning, outcomes improve for veterans, costs are reduced, and communities are strengthened nationwide.” Her passion is ensuring people are seen, heard, and supported.