Holly Trifiro is chief executive officer of Future Ready Cleveland, where she leads the organization’s work to expand access to high-quality learning opportunities for Cleveland students. She directs the organization’s investments and partnerships to advance school quality and expand access across the city’s education ecosystem. Her work focuses on aligning philanthropic capital, advising leaders across the education ecosystem, and increasing clarity and transparency around school quality so more students have access to effective learning over time.

Previously, Holly served as chief education officer for the City of Cleveland in Mayor Justin M. Bibb’s cabinet. In that role, she advised on citywide education strategy and policy across the education landscape serving nearly 60,000 students. She worked with school system leaders, board members, and community partners to align resources, support pandemic recovery, and strengthen coordination across the city’s education landscape. She co-founded Cleveland Reads, a citywide literacy initiative that mobilized schools, families, and community organizations and surpassed its first-year goal with more than three million books read in eight months.

Holly spent more than a decade with Teach For America, including nine years as executive director in Greater Cleveland and across Ohio. She led efforts to recruit and develop educators, strengthen partnerships with school systems, and expand access to opportunity for students statewide. She was also a founding member of Teach For America’s Systems Impact and Reinvention Labs, national initiatives focused on advancing systems improvement and reimagining public education.

Inspired by witnessing educational inequity growing up in Northeast Ohio, she began her career as a secondary English teacher. Holly holds a Master of Arts in Teaching from Johns Hopkins University and a Bachelor of Science in communication studies from Ohio University. She serves on the board of Greater Cleveland Works, reflecting her commitment to advancing economic mobility through education in the region.