2026 Business Leaders of the Year: Kylie Cassady

At 2 Oddballs LLC, Kylie Cassady serves as co-owner, co-founder and director of client strategy. Along with her husband, co-owner Gabriel Cassady, she leads a Springfield marketing agency that she describes as creative, strategic and people-centered.

Cassady says she’s most proud of 2 Oddballs’ culture – in part because the company is willing to do things differently, even when it means making some hard choices. Through success and growth, and through tough seasons including health challenges, she says she and her team work to keep the firm feeling like “them.”

Inside the company, Cassady says she builds systems that cultivate critical thinking and what she calls “healthy dissent.”

“I don’t want a team that simply agrees with me,” she says.

Team members are not only allowed but expected to notice issues, ask hard questions and raise alternative ideas. Cassady says she wants colleagues who care enough about the work to say, “What if we tried this in a different way?” Many of the firm’s best projects, she says, begin that way.

“Most of all, I’m proud 2 Oddballs has become a place where creativity and care can coexist with good business,” Cassady says.

Her leadership philosophy is rooted in what she calls “teamship,” which values trust, hard work and honest collaboration over hierarchy. Cassady says she believes people pay more attention to the things leaders consistently do than to what they repeatedly say. She says teamship means showing up on time, taking on unglamorous tasks, following through on commitments and being willing to get in the weeds with the team instead of standing apart from the work. She even cites “a keen awareness of my own limitations as an individual.”

That approach extends to 2 Oddballs’ client work. The agency serves local nonprofits, small businesses, regional companies, national brands and even the U.S. Navy. Regardless of size or sector, Cassady says the objectives tend to look similar: help organizations speak their truth, build trust with the people they need to reach and clear the way for meaningful progress toward a goal. Sometimes that looks like a new brand or website; other times it is a long-term campaign, public relations work or a social media strategy.

Cassady views community leadership through the same teamship lens. She says one of the most important things a leader can do is simply show up. She means this literally and figuratively, whether that be through volunteering with organizations doing meaningful work, attending events that support other business leaders or listening before assuming.

That commitment leads to service on the Associate Board of Directors of The Drew Lewis Foundation Inc. alongside leadership roles in Generation Next and the Springfield Contractors Association. Through both her company and her community involvement, Cassady aims to use her skills and connections to help people and organizations be understood, and to demonstrate that strong, sustainable results can come from investing in a culture built on curiosity, candor and care.