The 2026 Fall Wisconsin Skyward User Group Conference is on October 19-20, 2026 in the Wisconsin Dells.
The Wisconsin Skyward User Group provides a forum for Skyward® software customers to become better-educated users and to make suggestions for enhancing the software.
The Wisconsin Skyward User Group is organized as a non-profit corporation (501(c)(3)) under the laws of the State of Wisconsin. The organization endeavors to carry out its mission by:
conducting conferences to provide educational software users with an opportunity to become acquainted and exchange information for the utilization of the software and equipment;
to discuss ideas for new software and related products;
to provide a support resource for educational software users to communicate problems and expectations; and
to provide educational software users with a list of contacts in other school districts to share information
The Wisconsin Steering Committee members have a strong voice/vote in the Product Ideas Portal. We act as the advocate for Wisconsin’s Skyward® users; meeting with Skyward® staff to review product ideas in order to give our feedback on important functionality and priorities for the state of Wisconsin.
Our conferences are a great place to learn about Skyward's® new and improved features, discover tips and tricks, learn best practices, explore functions and techniques to streamline tasks to become more efficient in your job. It's also a great place to interact and share insights with fellow Skyward® users, leaders, and exhibitors.
The Wisconsin Skyward User Group steering committee member are employees of Wisconsin Skyward® School Districts who volunteer their time and labor. Each committee member plays a vital role in the planning of the Wisconsin Skyward User Group bi-annual conferences held each spring and fall.
The Wisconsin Skyward User Group traces its origins to 1983, during the early years of the growth of Skyward. The organization was originally established as the Software and Service User Group, Inc. by employees and users from Wisconsin school districts who relied on Skyward’s software systems for student information, finance, payroll, and school administration.
In the early 1980s, Wisconsin school districts were rapidly adopting computerized administrative systems. As more districts implemented these programs, school employees recognized the need for a collaborative network where users could exchange ideas, troubleshoot problems, and influence software development.
The user group emerged from this environment in 1983. Its founders envisioned a cooperative forum where business managers, payroll specialists, human resources staff, technology directors, and student services personnel could learn from one another and collectively advocate for improvements to the software.
Throughout the 1980s and 1990s, the organization expanded alongside Skyward’s growing customer base in Wisconsin. Semiannual conferences became one of the group’s defining activities. These conferences provided training sessions, software demonstrations, peer networking opportunities, and direct communication with Skyward staff and developers. School district employees could share solutions to common administrative challenges and discuss emerging educational technology needs.
The conferences also strengthened collaboration among Wisconsin school districts at a time when digital school administration was still developing. By bringing users together regularly, the organization helped standardize practices and encouraged schools to use technology more effectively for attendance reporting, grading, payroll, budgeting, scheduling, and state reporting requirements.
The organization formally operated for many years under the name Software and Service User Group, Inc. and eventually became a registered nonprofit corporation in Wisconsin. Public nonprofit records identify the organization as having been formed in 1984, reflecting its incorporation period shortly after the original founding activities began in 1983.
In 2015, the corporation officially changed its name to the Wisconsin Skyward User Group, Inc., reflecting the now-universal association with Skyward software and the organization’s established identity within Wisconsin schools.
Over time, the Wisconsin Skyward User Group evolved into one of the most active state-level Skyward user organizations in the country. The group’s steering committee, composed of volunteers from Wisconsin school districts, became an important liaison between school users and Skyward leadership. The committee advocated for software enhancements, reviewed proposed features, and represented the priorities of Wisconsin schools in product development discussions.
The organization also contributed to professional development for thousands of school employees. Its conferences in locations such as Wisconsin Dells became regular gatherings for district personnel seeking training on new software features, state reporting changes, and best practices in educational administration.
Today, the Wisconsin Skyward User Group continues to serve Wisconsin and other state's educational institutions as a nonprofit professional organization dedicated to collaboration, training, and software improvement. More than four decades after its founding, the group remains rooted in the same principles established in 1983: cooperation among school districts, user education, and a commitment to improving administrative technology in education.