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From Trinidad to Oxford to PMI: David Cumberbatch on Reinventing Career Readiness in the Age of AI

Laurel Donnellan sits down with David Cumberbatch, newly appointed Managing Director of North America for the Project Management Institute (PMI), for a wide-ranging conversation on education, career readiness, and leadership in a rapidly changing world of work. David traces his path from a childhood in Trinidad and Tobago โ€” shaped by a grandfather who ran the country's largest orphanage โ€” through Oxford as a Rhodes Scholar, to formative years at Procter & Gamble and Microsoft, and now to leading PMI's 800,000-member global community.

Along the way, he and Laurel compare the British and American education systems, unpack why Generation Beta may hold 18 to 30 jobs across 7 to 10 career chapters, and discuss the delicate balance of introducing technology and AI to young learners. The conversation turns to PMI's own AI transformation โ€” including its new CPM AI credential, the PMI Infinity AI companion platform, and an updated PMP exam that now includes AI and sustainability content.

David makes the case that durable "power skills" like critical thinking and interpersonal communication matter more, not less, as AI reshapes project work, and shares how PMI is building accessible pathways (like the CAPM certification) for people without a four-year degree to reach six-figure project management careers. The episode closes with David's reflections on leadership: the foundational role of safety and trust in lasting relationships, the lesson he carried from PNG's promotion-from-within culture versus Microsoft's "up or out" model, and his belief that compassionate leadership and competitive excellence aren't in tension โ€” they're the same thing.

Guest Bio: David Cumberbatch is the Managing Director of North America for the Project Management Institute (PMI), overseeing the U.S., Canada, and the Caribbean. Raised in Trinidad and Tobago, David earned a double honors degree in computer science and economics from the University of Kent at Canterbury, then studied at Oxford as a Rhodes Scholar. His career spans Procter & Gamble, Microsoft, the Gates Foundation, and ACT, with the last 20 years focused on the intersection of education, technology, and workforce readiness.

Resources & Links Mentioned

  • PMI website: pmi.org
  • PMI job board (for certified members)
  • PMI Infinity (PMI's AI companion platform)
  • CPM AI Certification and CAPM/PMP certification pathways
  • PM Ready certificate (high school level)
  • University of Pennsylvania high school internship training program
  • Crimson Global Academy (referenced re: UK/US K-12 comparison โ€” see Laurel's earlier interview)
  • Opportunity@Work (referenced re: non-degree career pathways)