Gartner Expert

Alastair Woolcock

Sr Director Analyst

Alastair Woolcock is a Senior Director Analyst, focusing on GTM strategy, marketing, product management strategy, positioning, channels, sales performance and culture. He is a member of the research groups in customer engagement, analytics and AI, plus digital business leaders. Mr. Woolcock focuses on C-level executives in the Fortune 500 and high-velocity growth emerging companies to help them anticipate changes to business models and consumer trends. He helps organizations understand "how" to build executable strategies for immediate results and change while having a vision for the next three years to improve their market position and growth.

Previous experience

Prior to joining Gartner, Mr. Woolcock was a Strategy Management Consultant to marquee brands in the Fortune 100 space focused on digital engagement, sales transformation, new market development, managed services, and outsourcing. Verticals serviced ranged from high-tech, transportation, retail, oil and gas, and finance in USA, Canada, Mexico and Western Europe.

He has held leadership positions with Long View Systems, Credera, Trafalgar Capital and CAVU Global, where he helped to expand and open new markets domestically and internationally, engage with product development, and build high-performance/high-velocity sales and marketing organizations.

Mr. Woolcock has been an interviewed previously on market changes by CNBC, Fox Business News, CRN Magazine and Oilweek Magazine.

He was a Sr. Executive Leader opening net new market teams in three countries, aiding and driving offering development with practice/product leaders, along with building sales and marketing organizations. He lead strategy teams for market messaging and GTM approach. He built outsourcing ITO services for midmarket to enterprise teams. He lead numerous channel development strategies with global OEMs through to new market entrants both as an external adviser to strategy organizations and internal use.

Boutique strength in developing service offerings in Blockchain, AI & Analytics impact on revenue creation and customer engagement.

Externally, Mr. Woolcock consulted with clients like McDonald's, Alteryx, Bremer Bank, National Bank of Canada, Hess, WestJet Airlines and more on digital strategy, outsourcing approach, sourcing strategy, and pricing. He led IT transformation through sourcing and digital engagement for revenue growth.

Professional background


Principal (Strategy)

Long View Systems

North American General Manager SBS

Trafalgar Capital


Areas of coverage

Marketing Leadership and Strategy

Business Performance Management for Tech CEOs

Product Messaging and Differentiation

Product Marketing Impact

Product Marketing Leadership


Presidents Scholarship, University of Victoria

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Top Issues That I Help Clients Address

1Developing a Go-to-Market Strategy and Framework

2Geo Expansion

3Sales and Marketing futures - RevOps

4Sales Enablement and Effectiveness

5AI Futures in Sales