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Kailey Jackson (Bowen)
Kailey Jackson (Bowen), a 2017 Gross Catholic graduate, is finding a meaningful way to give back to the school that helped shape her by bringing TeamMates Mentoring to Gross Catholic.
After graduating from Gross Catholic, Kailey attended the University of Nebraska at Kearney, where her involvement in campus leadership, volunteering, and community organizations sparked a lasting passion for serving others. She later returned to Omaha in 2022, drawn home in part to be there for her younger brother Jay during his senior year at Gross.
Coming back to campus reminded Kailey just how much Gross Catholic meant to her. “Returning and seeing Cougar alumni of all ages come together to support the teams, and experiencing the excitement of making it to state football, brought back the magic of Gross that I had missed,” Kailey said. “In those moments, I realized that no matter how much time had passed, Gross Catholic would always feel like home.”
Her return to Omaha also led her to the TeamMates Mentoring Program. After serving as the Program Coordinator for the Papillion-La Vista Chapter, Kailey joined the TeamMates National Office as a Marketing Specialist, where she now advocates for mentoring and works to bring awareness to the organization founded by Tom and Nancy Osborne 35 years ago. Mentoring has become deeply personal for Kailey. She currently mentors four students, including one entering her senior year and three post-secondary students.
That belief in the power of connection is what inspired Kailey to advocate for bringing TeamMates to Gross Catholic this school year. She sees the program as an opportunity to create meaningful relationships between students and mentors and a natural way for Cougar alumni to give back to the next generation.
“What I find most beautiful about mentoring is that each of my mentees is different from me in race, culture, upbringing, and interests, yet we connect so naturally and consider one another friends,” she said. “Mentoring simply requires an open mind and a willingness to sit with someone whose experiences may differ from your own. When you do, you often discover that you have more in common than you expected.”
For Kailey, giving back to Gross is already a family tradition. Her mom, Lisa, aunt, uncle, cousins, and siblings are all Gross Catholic alumni, while her dad has been part of the Gross community for more than two decades as a coach. Kailey continues that tradition through her service on the Gross alumni committee and by helping with art camp each summer. “Gross Catholic gave me so much, and I’m grateful for the opportunity to come back and be part of something that can make a difference for students,” Kailey said.
Through TeamMates, Kailey is helping create the same kind of connection she has always valued at Gross: people showing up for one another, building relationships, and making their community stronger. From growing up in the gym and on the football field to returning as an alumna and helping lead the next generation of Cougars, Kailey’s story is a reminder that once a Cougar, always a Cougar.
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