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Casper Oelofsen

Casper Oelofsen

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Director @ Serial Entrepreneur - Seasoned Exec Coach - Thinking Partner Complexity
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Education

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University of Stellenboch (Faculty of Medicine)

Post Graduate Certification, Design of Mindfulness Based Applications 2013-01-01 - 2016-01-01
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Stellenbosch University

Bachelor of Economic Science, Facilitation 2004-01-01 - 2005-01-01
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University of Cape Town

Coaching for excellence, Coaching 2004-01-01 - 2004-01-01
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Stellenbosch University

BEcon, Economics, Marketing, Industrial Pscychology 1989-01-01 - 1992-01-01
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International Bateson Institute (Sweden)

Certification Warm Data Facilitator, Complexity Thinking 2020-08-01 -

Work Experience

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Mindfulleadership

Current

Mindfulleadership

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WeR1 Corp. https://www.wer1tribe.io/

Current

WeR1 Corp. https://www.wer1tribe.io/

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https://batesoninstitute.org/warm-data/

Current

https://batesoninstitute.org/warm-data/

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www.complexityfit.com

Current

www.complexityfit.com

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Enneagram

Current

Enneagram

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Bethefuture

Current

Bethefuture

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Integral Coaching South Africa

2004-01-01 - 2004-01-01

Integral Coaching South Africa

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Cash Crusaders

2002-01-01 - 2004-01-01

Cash Crusaders

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Capitec

1998-01-01 - 2002-01-01

Capitec

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Bologna Rugby Club (Italy)

1993-03-01 - 1996-12-01

Bologna Rugby Club (Italy)

Skills

Leadership Development Recruiting Personal Development Executive Development Management Development Executive Coaching Emotional Intelligence Culture Change Workshop Facilitation Project Management Coaching Change Management Strategic Planning Leadership Management Consulting Strategy Marketing Team Building Entrepreneurship Career Development

Summary

Casper Oelofsen is an experienced executive business coach and strategic thinking partner, helping executives and organizations navigate the growing complexity of today’s fast-changing world. Drawing on a rich background in mindfulness, leadership, complexity science, and systems thinking, he works alongside leaders to cultivate agility, resilience, and innovative approaches in the face of uncertainty. Casper’s approach blends leadership development, team effectiveness, and complex systems thinking, using dynamic metaphors like orchestras and wilderness tracking to bring these concepts to life. He collaborates with top industry thinkers and leverages transformative tools like the Enneagram, Cynefin Framework, Warm Data, and the Thinking Environment to foster deeper insights and more effective decision-making. As a serial entrepreneur, strategist, consultant, and facilitator, Casper has founded multiple successful ventures over the past 25 years. He served in various leadership roles, including Chairman of Keymatrix Pty Ltd at age 32, where he played a key role in facilitating the listing of Capitec Bank Ltd—twice named the best bank in the world. His extensive experience in business and leadership makes him a practical, results-driven coach, adept at addressing his clients’ core challenges and opportunities. His client portfolio includes notable companies such as Facebook, MunichRe, Hewlett Packard, the Johnson & Johnson Group, Woolworths, Santam, British Petroleum (BP), CompTIA, Beiersdorf International, Discovery Health, MultiChoice (Mweb), The Jupiter Drawing Room, Quirk, Sanlam, Nedbank, Old Mutual SA, Standard Bank, ABSA, McKinsey India, CompTIA, Coronation, RMB, Londolozi, Singita, Relais & Châteaux, Unilever, Goldbeck (CEE), among others. ​Casper is a highly-regarded presenter and instructor at conferences in these cities: Las Vegas, San Franciso, Copenhagen, Melbourne, Budapest, Helsinki, New Delhi, Johannesburg, and Cape Town.

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