Alastair Woolcock guides senior leaders in global enterprises to strategically integrate advanced Artificial Intelligence—including Generative AI, emerging Reasoning Models, and Agentic AI systems—into their core operations and commercial revenue models. His research and advisory work explores how these technologies are reshaping modern work, digital labor, enterprise innovation, explainable decision-making, and the future trajectory toward AGI (Artificial General Intelligence). Alastair is an active speaker and keynote presenter for Gartner on AI Research.
He focuses on enabling executives to leverage AI to:
• Redefine product and services innovation and intelligent go-to-market strategies for digital labor
• Scale performance in sales, marketing, and customer success through AI-first design
• Anticipate and prepare for the transformative business, economic, and governance implications of AGI
Alastair’s global market experience (North America, Europe, China, Singapore, India, GCC, and Australia) is complemented by a distinguished career: Gartner Vice President & Analyst, former Chief Strategy Officer at a Goldman Sachs portfolio company (Revenue.io), Founder of CAVU Global AI (digital human and intelligent agent solutions), and Partner roles in investment and venture capital (Trafalgar Capital, Dreamfield Ventures). Insights from his work have been featured in The Wall Street Journal, CIO Magazine, CNBC, and Fox Business News.
Alastair Woolcock’s career has been consistently centered on leveraging emerging technology for strategic advantage, with an increasing emphasis on AI research and enterprise transformation.
As Chief Strategy Officer at a Goldman Sachs portfolio company, he integrated AI into new products, sales, and customer engagement strategies for Fortune 100 companies across high-tech, transportation, retail, energy, and financial services markets in the USA, Canada, Mexico, and Western Europe.
Further demonstrating his leadership in AI and digital transformation:
• Founded CAVU Global AI: An entrepreneurial venture developing digital human AI and early-stage agentic systems.
• Venture Capital & Consulting Leadership: As a Partner at Trafalgar Capital and Principal at Credera, he spearheaded initiatives in AI, intelligent systems, and digital strategy.
• Global Enterprise Advisory: Guided IT and AI-driven transformations for global corporations in Retail, Oil & Gas, Telecom, and Financial Services.
• Recognized Thought Leader: Frequent keynote speaker and media contributor, providing expert insights into the evolution of AI, the rise of reasoning models, and the path toward AGI.
CAVU Global AI, Partner, 4 years
Credera, Principal, 1 years
Gartner, Vice President, Analyst, 4 years
Long View Systems, North American General Manager SBS, 13 years
Revenue.io, Chief Strategy Officer, 2 years
Trafalgar Capital (Hedgefund), Managing Director, 3 years
Artificial Intelligence
Technology Buying Dynamics
Sales and Revenue Technology
Technology Innovation and Strategy
Generative AI Resource Center
Presidents Scholarship, University of Victoria
How to use AI and GenAI in enterprise
GTM market strategy
Sales & Marketing organizational strategy
Futures in AI, GenAI in go-to-market models
use of AI and it's impact on citizens for governments and government services