Meet Matthew Barry, New CEO of TRAILS

TRAILS is incredibly excited to announce that Matthew Barry starts today, April 6, as its next CEO. Matthew brings deep expertise in education technology, school support systems, and social impact ventures, and his arrival marks the start of an exciting new chapter at TRAILS. Under his leadership, TRAILS will be shifting toward offering a more tech-enabled product designed specifically for our target users and the unique context of the school environment, and optimized for equitable, lasting impact at scale.


Most recently, Matthew served as a Partner at Learn Capital, where he led and supported investments in early- and growth-stage ventures focused on education, workforce development, and AI-enabled learning platforms. He was also responsible for the firm's impact management practice, designing frameworks to assess and scale the societal value of portfolio companies. 


Learn Capital is one of the longest-standing and most prominent venture firms focused exclusively on education and human capital development, with approximately $1 billion in assets under management, backing companies that expand access, improve outcomes, and advance the science of learning.


Before joining Learn Capital, Matthew’s career spanned data science, philanthropy, and urban development — always with an eye toward both large-scale change and tangible community impact. He is also the proud dad of a teenage son.


TRAILS has reached more than 600,000 students across 2,000+ schools. Under Matthew’s leadership, TRAILS will continue to evolve to optimally support its school partners and ensure they are well equipped to deliver essential mental wellness programming to their students. TRAILS founder, Elizabeth Koschmann, will remain with the organization for the foreseeable future to assist in Matthew’s transition and to ensure he has every opportunity for success.