Jordan Tilleson’s journey of service began with a raised hand and a clear heart. He still remembers the moment he enlisted—an impassioned choice rooted in a deep desire to serve something larger than himself. From those first steps as an Infantry enlistee to rising through the ranks as a commissioned Armor officer, Jordan’s path led him through two deployments to Iraq. There, amidst the dust and discipline, he earned more than medals—he discovered the quiet strength of human connection. In the trenches, he learned a lesson that would guide every step thereafter: genuine appreciation builds unbreakable bonds.

When Jordan moved to his hometown of Stoughton, Wisconsin, he didn’t hang up his leadership hat. Instead, he brought it to the civic arena. In April 2025, he was elected as District 2 Alderperson—an achievement born not of flashy speeches but of humble conversations. He didn’t just campaign on policies; he knocked on doors, asked questions, and truly listened. His secret? He inspired participation by showing people their voices mattered, awakening in them the belief that change was possible through shared effort.

Whether at City Hall or on a Board, Jordan begins every meeting and gathering the same way—with open acknowledgment of the people around him. From fellow board members to community volunteers and veterans, he offers sincere praise and thoughtful recognition. It’s not performance, it’s principle. Even when discussing complex issues like stormwater infrastructure or public library budgets, he leads with empathy, avoids needless criticism, and listens with the intent to understand. For Jordan, the surest path to change is through respect.

Beyond municipal borders, Jordan’s dedication extends to those who have worn the uniform. As the Legislative Chair of the Wisconsin VFW, he walks the halls of the State Capitol in Madison and Congress in Washington, D.C., advocating for causes close to veterans’ hearts—tax credit relief, POW/MIA funding, and more. His sharp suits may turn heads, but it’s his calm conviction and narrative-driven advocacy that win the room. Whether meeting with Representative Mark Pocan, Senator Tammy Baldwin, or Representative Derrick Van Orden, Jordan speaks in stories—not demands—framing each issue around shared purpose and common good.

At VFW Post 328, where he serves as Junior Vice Commander, Jordan lives by a simple rule: praise the slightest improvement and do it sincerely. Every volunteer effort, every successful event—especially National Day of Service moments—gets the recognition it deserves. He makes people feel seen and important, building a culture of encouragement that draws others in and keeps them engaged.

Blending over 25 years of experience in policy work and entrepreneurship, Jordan brings both vision and precision to the table. Whether streamlining development processes or refining municipal billing systems, he ensures stakeholders are part of the solution. His leadership isn't about giving orders, asking questions, sparking ideas, and creating shared ownership of outcomes.

Even on social media and in the spotlight, Jordan’s leadership feels personal. His warmth shows through in every handshake, every smile, and every hug. He believes a name remembered and a story shared can open more doors than any title.

Through every chapter—on the battlefield, in city chambers, and among fellow veterans—Jordan Tilleson leads with heart. His commitment to servant leadership, rooted in appreciation, authentic connection, and respectful influence, continues to unite people, spark progress, and uplift his community—from the streets of Stoughton to the halls of Congress.