Waukesha's United Way history began in 1930 when a local schoolteacher, Raymond Rupple, organized an effort in the community to provide the basic needs of food, shelter and clothing to Waukesha County residents impacted by the Stock Market crash of 1929. In the Fall of that year, the organization formally became the Waukesha Community Chest. Rupple remained the director of the organization until he retired in 1968. He was succeeded by Walter Baranowski who held the position until 1979 when William Nantell became United Way's third Executive Director. Mark Johnson assumed the responsibilities in 1987, and since 1996, United Way in Waukesha County has been led by Executive Director, Jayne Thoma.

The name of the organization changed several times through the years. The Waukesha Community Chest became the Greater Waukesha United Fund in 1962. Ten years later, the name was changed to United Way and finally to United Way in Waukesha County in 1973.
United Way in Waukesha County currently partners with 38 organizations. Several of those organizations, The YMCA, Boy Scouts, Salvation Army and American Red Cross have been receiving funding from United Way since 1932. Programs funded by United way are determined by community need and results produced.

As United Way entered the 21ST century, it began a transformation to a "Community Impact" organization. United Way continues to fund programs that directly impact individuals and families, but also added another approach called Community Impact. This approach looks at improving lives from a community-wide perspective. Community Impact identifies, focuses on and impacts the root or underlying causes of problems existing in the community. The goal of Community Impact is to make lasting changes in community conditions.