Jon Aleckson for Wisconsin State Assembly

Meet Jon

I Am Jon Aleckson

Hear directly from Jon about why he is running to serve District 50.

Meet Jon

Who Is Jon Aleckson?

Jon is a husband, father, and grandfather who has called Wisconsin home his entire life. He and his wife Mary live on 17 acres in the rural Town of Springdale near Mount Horeb, where they have been active members of St. Francis Catholic Church for 37 years. Jon also serves on the board of a Middleton free clinic, putting his faith and community into action every day.

A retired small business leader, Jon founded and led Web Courseworks, an educational software company, from 1992 to 2022. He knows how to balance a budget, create jobs, and deliver results with fiscal responsibility—skills Wisconsin needs in Madison.

Jon formerly taught as an adjunct professor at UW–Platteville. He is not a career politician: Jon pledges to serve only 2–4 years in the Assembly, solve real problems, and leave District 50 stronger for the next generation.

Why Jon Aleckson Is Qualified to Serve

He’s not a politician. He has real-world experience and success—the real thing.

Builder & Entrepreneur

Founded Web Courseworks in 1999 and led it for 24 years, serving the U.S. State Department, McDonald’s, and the World Anti-Doping Agency. Navigated recessions and technological change, then successfully transitioned leadership in 2021. He knows how to build, sustain, and leave something better than he found it.

PhD Educator

Doctor of Philosophy in Educational Leadership from UW-Madison—earned part-time while running a company. Taught graduate-level courses at UW-Platteville. Published two books on collaboration. When he talks Smarter Schools, he’s speaking from a career, not a talking point.

Collaborator & Team Builder

Author of MindMeld and The Expert’s Halo. Spent 24 years leading teams of programmers, designers, and educators toward a common goal. Working across the aisle in Madison requires exactly that skill.

Fiscal Conservative

Built successful products and teams on tight budgets for over two decades. Supports returning Wisconsin’s budget surplus to schools, special education, and property taxpayers. The discipline that built a company will guide every vote in Madison. The people must get all the government for which they are paying.

Wisconsin Neighbor, Not a Career Politician

Cedarburg raised. Cross Plains family. Town of Springdale since 2008. Married to Mary. Three Wisconsin-raised children. Five grandchildren in Dane County. Board member of a free healthcare clinic for the uninsured in Middleton. Pledged to serve 2–4 terms and always put the district first.

“I’ve raised a family and built a successful Wisconsin business—now I want to bring that practical experience to Madison. This isn’t about a political career. It’s about working together to solve real problems and leave Wisconsin stronger for the next generation.”

— Jon Aleckson, April 17, 2026

Download Jon’s Full Resume (PDF)