While living in Winchester, Hill became active in organizing African-American laborers, sharecroppers and tenant farmers. They worked for white landowners at a disadvantage, as they were dependent on the owners' dispersing funds and settling accounts after they sold the cotton crops. The landowners seldom provided itemized accounts, often required sharecroppers to buy seeds and supplies from plantation stores, and sold the cotton according to their own schedules. Sharecroppers often struggled financially for months after delivering cotton to the landowners and before receiving any payments.