As part of the ongoing celebration of our 25th anniversary, we spoke with Katie Cunningham, senior director of national program operations, about her path to College Possible, her work building strong teams and systems that support students nationwide, and her contributions to transformational initiatives like Coach Possible. Her leadership underscores how we combine coaching, data and technology to expand access, improve outcomes, and ensure students can pursue the futures they imagine.
Katie Cunningham’s journey to College Possible began in the classroom. After teaching fourth grade with Teach for America, she saw how students’ circumstances shape the opportunities available to them. She was drawn to College Possible because it supports students at every step of their journey to and through college. “What keeps me inspired is seeing that impact extend beyond one student—when a student graduates, it can influence their family, their community, and future generations,” she says.
One moment stands out in Cunningham’s memory. Early in her time at College Possible, she took a high school student to a leadership conference. That student went on to attend college with a full ride, graduate, returned as a College Possible coach, and now works with the organization full-time. “Seeing a student’s journey come full circle—that’s when I truly realized the impact of what we do,” Cunningham recalls.
Over the years, she has watched College Possible grow from helping a few thousand students to more than 25,000 annually. She’s especially energized by how the organization leverages data and technology to better support students. “AI and data don’t replace our coaches, but they do allow us to reach more students, provide smarter guidance, and make our programs more sustainable. We’re shaping the future of student support in ways that weren’t even imaginable five years ago. It’s exciting to be part of that transformation,” she says.
For Cunningham, making college possible means opening doors that might otherwise remain closed. “It’s not just about admissions,” she adds. “It’s about helping students every step of the way so they can build the life they want. Your zip code shouldn’t limit your dreams.” She credits her own success to caring adults who guided her, and now she dedicates herself to paying it forward to future generations of students.
Her advice to students is simple but powerful: “You belong in the spaces where decisions are made. You are smart, capable, and you belong. Keep showing up. You have support all around you—even from people you might not see. Ask for help. Keep going.”
Through her leadership and dedication, Cunningham exemplifies College Possible’s mission. Each student carries forward that vision, proving that with guidance, encouragement, and perseverance, remarkable outcomes ripple outward, creating opportunities for students and the communities they touch.
More about Katie
Katie Cunningham is the senior director of national program operations at College Possible. She leads the teams and systems that help students across the country get the guidance they need—from high school through college graduation.
In her more than nine years with one of the largest college access and success organizations, Katie has worked at every level of student support, from campus coach to program manager, giving her firsthand insight into what helps students succeed. She ensures programs run smoothly, supports coaches in delivering personalized guidance, and builds tools and processes that make operations more efficient. Katie also pilots new initiatives, develops national partnerships, and helps scale College Possible’s impact—always keeping the human connection at the center of every student experience.
