The Center for Education Reform Announces Powerhouse New Leadership Team to Advance Education Freedom and Innovation

August 5, 2025

WASHINGTON DC — The Center for Education Reform (CER), the nation’s leading advocate for school choice, innovation, and excellence in education, today announced the addition of three accomplished leaders to its senior team. With deep experience spanning policy, government affairs, communications, education operations, and ed tech innovation, the new team reflects the importance of this moment and underscores CER’s commitment to driving bold reforms and empowering families with educational options.

Caroline Casagrande joins CER as Chief External Affairs Officer, bringing decades of expertise at the intersection of education, policy, and politics. Casagrande most recently served as Executive Director of Government Relations at Stride, Inc., where she led massive growth in their career education and adult education programs and oversaw all state and federal education technology policy efforts. She also served as Deputy Assistant Secretary of State for Academic Programs. A former New Jersey legislator — the youngest woman ever elected to the state assembly — and a former litigator, Casagrande is widely recognized for her strategic leadership, her ability to forge impactful partnerships, and her track record of driving meaningful change in education policy.

“This moment in education is too important to sit on the sidelines. I had to get closer to the fire, working shoulder-to-shoulder with the architect of the modern education reform movement to advance real change,” said Casagrande. “Joining Jeanne Allen and the CER team is a natural next step in my lifelong commitment to freedom and opportunity for all kids.”

Also joining CER as Chief Operating Officer is Kirk Benningfield, an accomplished education operations leader who has held senior roles at Pearson and innovative ed tech startups, serving as Vice President of Education Operations at Smarthinking. Benningfield holds a PhD in mathematics and brings unmatched expertise in operational excellence and scaling education solutions.

Jonathan Oglesby steps in as Senior Director of Communications, rejoining CER after more than a decade. He brings a wealth of experience in implementing media strategy, digital advocacy, and message development for education-focused organizations. Jonathan was previously the Director of External Affairs for iNACOL and consulted for a number of education companies and nonprofits.

They join Chief Program Officer Caroline Allen, who served as founding director of the Yass Prize in 2021 and oversees all awards, events and program activities for CER. Her passion for CER and the advancement of philanthropic efforts led by the Yass Prize is informed by her early career as a learning coach and a prized educator at one of the best charter schools in the nation.

“At CER we are relentless in pursuit of opportunity for kids, and that means having the most relentless team in the business,” said CER’s founder and CEO Jeanne Allen. “We now have a full bench of exceptional talent with deep knowledge and the kind of entrepreneurial urgency we demand of ourselves every day. Together we are doubling down on the fight to ensure every child in America can access the education they deserve — especially as CER works to influence policy and practice, celebrate the brightest innovators, and deliver measurable impact in this pivotal moment.”

Founded in 1993, CER continues to set the agenda on education reform, working with policymakers, innovators, and families nationwide to expand choices and elevate outcomes. Through initiatives like the Yass Prize for Sustainable, Transformational, Outstanding and Permissionless Education, CER shines a spotlight on and rewards the most innovative education providers transforming lives today, awarding over $50 million to more than 200 innovators and recognizing thousands of education providers nationwide.

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