Cheryl May

Digital Specialist, systemic.design at Systemic Design Association
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Contact Information
us****@****om
(386) 825-5501
Location
Toronto, Ontario, Canada, CA

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Katerina Cepero

While working for Cheryl, I was constantly inspired by her innovative leadership, not only in the sense of adapting new technologies but also in terms of approaching ongoing projects in new ways. She has a tremendous amount of positive energy and a natural skill of getting her team excited about taking on new projects and meeting goals.

Andrew Chung, CFRE

Cheryl knows how to inspire a team towards growth and change, and all the while doing it with a deep sense of integrity and relentless energy. She is incredibly cerebral and knows how to apply her innovative ideas towards tangible results that have wide-scale impact. I have never been more excited to work for and alongside anyone before than I was when working under Cheryl's leadership. She motivates others to drive results with confidence while challenging everyone around her to see the bigger picture beyond the bigger picture. Cheryl is a visionary who can take any problem and bring the right people together to find a great solution. Anyone would be so fortunate to work with her.

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Credentials

  • The Fundamentals of OCAP® (Ownership, Control, Access and Possession)
    First Nations Information Governance Centre (FNIGC)
    Aug, 2020
    - Nov, 2024
  • Orientation for Crown Corporation Directors
    Canada School of Public Service | École de la fonction publique du Canada
    Nov, 2019
    - Nov, 2024
  • Department for Women and Gender Equality's Gender-based Analysis+
    Government of Canada
    Aug, 2019
    - Nov, 2024
  • Tri-Council Policy Statement, Ethical Conduct for Research Involving Humans
    Government of Canada
    Feb, 2016
    - Nov, 2024

Experience

  • Systemic Design Association
    • Norway
    • Higher Education
    • 1 - 100 Employee
    • Digital Specialist, systemic.design
      • Mar 2021 - Present

    • Board Member, Secretary
      • Nov 2021 - Present

    • Digital Specialist, RSDsymposium.org
      • Jul 2020 - Present

  • Canadian Race Relations Foundation
    • Canada
    • Civic and Social Organizations
    • 1 - 100 Employee
    • Board Member
      • Feb 2018 - Mar 2022

      Joined Board of Directors in April 2018. CRRF is a Canadian Crown corporation. Board positions are Governor in Council appointments.

    • Senior Advisor, Board of Directors
      • Apr 2016 - Mar 2018

    • Senior Director, Strategy and Development
      • Feb 2014 - Mar 2016

  • Cheryl May Projects
    • Canada
    • Business Consulting and Services
    • Digital Specialist, WoundPedia.com (including International Interprofessional Wound Care Course)
      • May 2020 - Sep 2020

    • Digital Specialist, commonapproach.org, The Common Approach to Social Impact Measurement
      • May 2020 - Aug 2020

    • Evaluator, Innovation & Experimentation, North York Community House
      • Mar 2020 - Aug 2020

      Evaluation for a North York Community House three-year innovation project that simultaneously sought to improve service delivery and contribute to a culture of innovation. Deliverables include timeline reconstruction, environmental scan, document review, and confidential interviews.

    • Development Advisor, Fourth Sector 2030, United Nations Foundation
      • Nov 2018 - Jun 2020

    • Design Researcher, VapeHack, University of Toronto, Dalla Lana School of Public Health
      • Jan 2020 - Apr 2020

      A study for the Ontario Tobacco Research Unit (/www.otru.org) that explores youth vaping. VapeHack was a two-day hackathon-style event with seven facilitated online sessions, based on participatory co-design methods.

    • Adoption Strategist, Impact Dashboard, Centre for Social Innovation
      • Jun 2019 - Apr 2020

    • Senior Researcher, Microtasking Project, Toronto Workforce Innovation Group
      • Aug 2019 - Feb 2020

      https://www.microtasking.online/

    • Community Development, National Initiatives, Social Innovation Canada
      • Aug 2019 - Jan 2020

    • Development Advisor, Villa Charities
      • Jun 2019 - Sep 2019

    • Digital Specialist, Project ECHO, Ontario Skin and Wound Care
      • May 2019 - Jul 2019

    • Program Developer, The Refinery (accelerator for women-led ventures), Community iLab
      • Sep 2017 - Apr 2019

      Developed curriculum and led programming for The Refinery. Launched program and facilitated workshops for women entrepreneurs.

  • OCAD University
    • Canada
    • Higher Education
    • 500 - 600 Employee
    • Researcher, Futures of Canadian Identities
      • Oct 2016 - Mar 2017

      Canadian Heritage and Resilience Design Lab: Action Research and Capacity Building Project . Canadian Heritage and Resilience Design Lab: Action Research and Capacity Building Project .

  • MakeWay
    • Canada
    • Philanthropic Fundraising Services
    • 1 - 100 Employee
    • Project Director, The Base, Shared Platform
      • Dec 2012 - Jan 2014

  • Skills for Change
    • Canada
    • Non-profit Organizations
    • 100 - 200 Employee
    • Executive Director
      • Oct 2010 - Nov 2012

  • MaRS Discovery District
    • Canada
    • IT Services and IT Consulting
    • 200 - 300 Employee
    • Practice Lead, Social Innovation
      • Aug 2009 - Sep 2010

    • Social Entrepreneur in Residence
      • Jun 2008 - Jul 2009

  • Access Alliance Multicultural Health and Community Services
    • Canada
    • Hospitals and Health Care
    • 100 - 200 Employee
    • Interim Executive Director, The Neighbourhood Centre
      • Sep 2008 - Aug 2009

      Business design to support long-term merger strategy. Merged with Access Alliance. Business design to support long-term merger strategy. Merged with Access Alliance.

  • Cheryl May Projects
    • Canada
    • Business Consulting and Services
    • Development Consultant, Findhelp | 211 Central
      • Jan 2008 - Sep 2008

    • Development Consultant, Centre for Global eHealth Innovation
      • Jan 2008 - Mar 2008

  • Artscape
    • Canada
    • Non-profit Organizations
    • 1 - 100 Employee
    • Executive Director, Artscape Foundation
      • Jul 2007 - Dec 2007

  • Findhelp | 211 Central
    • Canada
    • Civic and Social Organizations
    • 1 - 100 Employee
    • Executive Director
      • Oct 2002 - Aug 2007

    • Director, Development
      • Apr 1999 - Sep 2002

    • Project Manager, Possibilities Project Virtual Employment Centre
      • Oct 1997 - Mar 1999

  • Canadian Stage
    • Manager, Corporate Sponsorship
      • Sep 1996 - Sep 1997

  • Hip Baby
    • Canada
    • Retail
    • 1 - 100 Employee
    • Founder and CEO, Absolutely Diapers (now Hip Baby)
      • Jan 1989 - Aug 1996

      Founded and scaled national retail corporation. Developed social enterprise and social franchise model dedicated to reusable products, and gender-neutral, no-logo clothing and toys. Business units built: retail, wholesale, manufacturing, import and export. Opened 13 stores, including one in Vienna. Exited in 1995. Acquired by Hip Baby. Founded and scaled national retail corporation. Developed social enterprise and social franchise model dedicated to reusable products, and gender-neutral, no-logo clothing and toys. Business units built: retail, wholesale, manufacturing, import and export. Opened 13 stores, including one in Vienna. Exited in 1995. Acquired by Hip Baby.

  • Cheryl May Projects
    • Canada
    • Business Consulting and Services
    • Producer, Flexible Packaging Plant
      • Sep 1985 - Jan 1989

      Alternative Theatre Company: Dora Award for Best Actor, and Nomination, Dora Award for Best Production

    • Theatre Director and Designer
      • 1984 - 1988

    • Graphic Artist and Content Writer
      • 1978 - 1987

    • Clothing Designer and Manufacturer
      • 1979 - 1982

  • Mount Sinai Hospital (Toronto), Sinai Health
    • Canada
    • Hospitals and Health Care
    • 700 & Above Employee
    • Executive Assistant, Dr. Donald Low, Chief of Microbiology
      • Jun 1987 - Dec 1988

  • University of Toronto
    • Canada
    • Higher Education
    • 700 & Above Employee
    • Manager, Helen Gardiner Phelan Playhouse
      • 1985 - 1987

  • Sun Media
    • Canada
    • Newspaper Publishing
    • 300 - 400 Employee
    • Columnist and Features Writer
      • 1978 - 1986

      Toronto’s alternative scene in music, theatre, art and independent retail.

    • Compositor, Graphic Artist
      • 1977 - 1978

  • Foresters Financial
    • Canada
    • Financial Services
    • 700 & Above Employee
    • Graphic Designer
      • 1979 - 1983

Education

  • London South Bank University
    PhD, Laws and Social Sciences
    2019 - 2025
  • OCAD University
    MDes, Strategic Foresight and Innovation
    2014 - 2017
  • University of Toronto School of Continuing Studies
    Business, Professional, and Entrepreneurial Studies
    1994 - 1995
  • University of Toronto
    Bachelor of Arts, English and Drama
    1984 - 1987
  • Centennial College
    Publishing and Design
    1977 - 1978

Community

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