Early Care and Education providers and Medicaid are natural partners to promote the well-being of young children and alignment the two sectors is increasingly prioritized. Nemours’ brief synthesizes lessons learned and important strategies developed from Nemours’ technical assistance to the District of Columbia, Maryland, and Washington to plan pilot initiatives to foster collaboration between the health care sector and early care and education sector. The Maryland toolkit shares sample documents developed through Nemours’ technical assistance project that could be used as templates for similar cross-sector projects in other states.