Gartner Expert

Alastair Woolcock

VP Analyst

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.

Previous experience

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.

Professional background

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

Areas of coverage
  • Artificial Intelligence

  • Technology Buying Dynamics

  • Sales and Revenue Technology

  • Technology Innovation and Strategy

  • Generative AI Resource Center

Education

Presidents Scholarship, University of Victoria

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Top Issues That I Help Clients Address

01

How to use AI and GenAI in enterprise

02

GTM market strategy

03

Sales & Marketing organizational strategy

04

Futures in AI, GenAI in go-to-market models

05

use of AI and it's impact on citizens for governments and government services