Gartner Expert

Alastair Woolcock

VP Analyst

Alastair Woolcock guides senior leaders in global enterprises to strategically integrate advanced AI—including Generative AI and emerging Agentic AI systems—into their core operations and commercial revenue models. His work focuses on leveraging these technologies to redefine product innovation, create intelligent go-to-market strategies, and unlock new levels of performance in sales, marketing and customer success. He possesses a keen understanding of the evolving path towards more generalized AI (AGI) and helps organizations prepare for its transformative business implications.

His global market experience (North America, Europe, China, Singapore, India, GCC, Australia) is complemented by a distinguished career: former Gartner VP Analyst (sales & marketing), Chief Strategy Officer at a Goldman Sachs portfolio company (Revenue.io), Founder of CAVU Global AI(a digital human AI company), and Partner at Trafalgar Capital (hedgefund) and Dreamfield Ventures, along with time at a Services Integrator (Long View Systems). Insights from Alastair's work on AI's strategic impact have been featured in the Wall Street Journal and CIO Magazine.

Previous experience

Alastair Woolcock’s career has been marked by a consistent focus on leveraging technology for strategic advantage, with an increasing emphasis on AI. As Chief Strategy Officer at a Goldman Sachs portfolio company, he pioneered the integration of AI into new products along with sales and customer engagement strategies for Fortune 100 companies in high-tech, transportation, retail, oil and gas, and finance across the USA, Canada, Mexico, and Western Europe.

Further demonstrating his leadership in technological innovation and strategic market development:

- Founded CAVU Global: An entrepreneurial venture focused on developing and deploying digital human AI and early-stage intelligent agent solutions.

- Led Key Initiatives in Consulting & Venture Capital: In roles at Credera (digital strategy), and as a Partner at Trafalgar Capital and Long View Systems, he spearheaded market expansion and product development initiatives centered on emerging technologies.

-Advised Global Corporations: Guided transformative IT and AI-driven strategies for major companies in Retail, Oil & Gas, Telecom, Financial Services, aimed at bolstering digital engagement and optimizing revenue growth.

-Shared Market Insights: Frequently provided expert commentary on the transformative impact of AI, including its trajectory and market implications, on prominent platforms such as CNBC and Fox Business News.

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

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