Cheryl May

WORK HISTORY

EDUCATION

SKILLS

ABOUT CHERYL MAY

My primary focus is on the scholarly and practice communities related to systemic design, which aligns with my research on systemic leadership in organisations with complex missions. I am actively exploring interdisciplinary and transdisciplinary approaches to sensemaking and problem-solving, particularly in relation to second-order cybernetics, transformational design, and performative futures.I am currently a doctoral researcher at London South Bank University, with completion in 2026. Alongside my academic work, I serve as executive editor of Contexts—The Systemic Design Journal and oversee the publication of the annual RSD proceedings. I am also executive advisor to the Systemic Design Association and co-curator of the Relating Systems Thinking and Design (RSD) symposium. In these roles, I contribute to field-building through reflective publishing, curating dialogue, and supporting community-led knowledge sharing. I also publish two ongoing newsletters focused on systemic design: This Week in Systemic Design and the monthly SDA newsletter. Both are part of a broader effort to support shared learning, surface emerging voices, and make the field more visible and connected.My career is grounded in evolutionary systems practice and social innovation, incorporating principles of emergence, adaptation, and interdependence to support systems in evolving from within, rather than through top-down change. My work spans diverse areas, including upcycling, social theatre, eco-parenting, information access and personal privacy, and diversity, equity, and inclusion. My practice combines a design mindset with strategic development and business modelling—from strategy design to fundraising.Previously, I served for 8 years as a strategic advisor and board member at the Canadian Race Relations Foundation. I served as social innovation practice lead at MaRS Discovery District and have held five executive director roles. A notable achievement was leading the development of the 211 information system in Canada during my time at Findhelp Information Services—an initiative recognised with the Head of the Public Service Award for Excellence in Service Delivery. Across these roles, I have advised and connected hundreds of organisations and raised over 100 million CAD.I hold an MDes in Strategic Foresight and Innovation from OCAD University and a BA in English and Theatre from the University of Toronto, as well as additional studies in Business and Entrepreneurship at the University of Toronto.