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Description
Keith McFarlane, CTO of Globality, has spent his career innovating inside some of the world’s most complex technology organizations—from Microsoft and Bell Labs to Oracle, LiveOps, and now an AI-driven sourcing platform reshaping how enterprises manage trillions in spend.
In this episode, Keith shares what innovation really looks like inside large enterprises, why process can quietly crush creativity, and how leaders can modernize legacy systems without slowing execution. Drawing on firsthand stories—including a formative lesson from Bill Gates—he explains why innovation must be tied to value, not novelty.
Listeners will walk away with practical insights on building AI-powered platforms at scale, leading continuous delivery in regulated environments, and making intentional career moves that expand both technical depth and business judgment.
Key takeaways include:
- Why real innovation requires tolerance for failure and individual empowerment
- How AI delivers value when paired with domain expertise, not hype
- Why strategic career risks accelerate long-term leadership growth
Key Takeaways
From Microsoft to Globality: A Career Built on Calculated Risk
“Every one of these steps felt risky—but each one filled a gap in my understanding.”
Keith reflects on moving across industries and roles to intentionally expand his perspective
Why Innovation Slows Down in Large Companies
“There’s a strong reaction against failure—and over time, that slows everything.”
Processes designed for safety often unintentionally suppress creativity.
Modernizing Legacy Platforms with Continuous Delivery
“Sometimes you have to convince people to take a leap before they see the value.”
At Oracle and Globality, Keith pushed delivery models that shipped faster without sacrificing stability.
AI That Solves Real Problems, Not Just Interesting Ones
“AI works when it shortens cycle time and delivers measurable outcomes.”
Globality’s decade-long AI investment shows how domain knowledge makes AI actionable.
Advice for the Next Generation of Tech Leaders
“Look for transitions that teach you something new—even if they feel risky.”
Keith urges leaders to seek discomfort and expand their breadth deliberately.
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This Episode's Guest
Keith McFarlane
Keith McFarlane is the Chief Technology Officer at Globality, where he leads the development of an AI-driven sourcing platform helping Fortune 2000 companies make smarter, faster decisions on enterprise spend. With a career spanning Microsoft, Bell Labs, Oracle, LiveOps, and Avaya, Keith brings deep experience building and scaling complex enterprise platforms across cloud, AI, and SaaS environments. Known for modernizing legacy systems and driving continuous delivery at scale, Keith blends strong engineering fundamentals with a sharp business mindset. He is passionate about building high-performing teams, empowering innovation inside large organizations, and applying AI where it delivers real, measurable value.
