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Henry May has held a variety of roles in their professional career. From 2012 to 2013, they were an intern at Procter & Gamble, where they researched and delivered a strategy for the company to grow scale through multibrand customer mailings. Henry then joined Enseña por Colombia, where they consulted on the organization's selection process, training institute, and organizational structure, and co-ordinated six first-year teachers in four public schools in Bogota. In 2013, they became a geography and history teacher for 6th grade students at Colegio San Jorge de Inglaterra - St. George's School, and designed new curriculum plans for both subjects. In 2011, they founded the Huracan Foundation, with the mission to support and empower Teach for All participants across the world to use football-based projects to transform the low-income communities of their schools in some way. In 2013, they co-founded Coschool, an organization to address the character and social/emotional skills gap that exists in schools in Colombia. In 2017, they became a board member for Liceo Boston and Liceo Moderno Walt Whitman, both bilingual private schools in Bogota. In 2018, they were selected as a Fellow for the Teach for All Social Innovation Fellowship and the GSBI program at Santa Clara University. In 2022, they were selected as a Fellow for the Transcend Fellowship Cohort 7.

Henry May attended Santa Clara University from 2017 to 2019, where they obtained a GSBI in Social Entrepreneurship. Prior to that, they attended Canterbury Christ Church University from 2009 to 2010, where they obtained a PGCE in Educación secundaria. Henry also attended the University of Nottingham from 2005 to 2008, where they obtained a Bachelor of Arts (BA) in Theology/Theological Studies.