King worked as a subcontracted employee for a variety of businesses around Wisconsin, writing human resources and accounting software for IBM 5100 computers.

In 1981, King wrote software for Merrill Area Public Schools, which was subsequently purchased by three other districts in Wisconsin.

[citation needed] In 2001, Skyward partnered with the Washington School Information Processing Cooperative (WSIPC) to integrate into 297 districts throughout the state.

In 2013, Rhode Island and Tennessee education departments both selected Skyward as a preferred vendor of student administrative software for their schools.

[citation needed] In March, 2016, Skyward moved all corporate operations to its new world headquarters building in Stevens Point, WI.