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Oct 21, 2025 36 min

Doug Roseborough

from The Hard Part with Evan McCann Hosted by Evan McCann

Doug Roseborough spent his career at multiple leading technology companies including 30 plus years at Oracle. Chapters 00:00 Intro 1:40 Early Days at Oracle 02:56 Oracle's Secret Sauce 05:16 Transition to the Bay Area 08:15 Rolling Out Pricing Models 10:31 Cultural Insights at Oracle 13:05 Leadership and Team Dynamics 15:35 Operations at Oracle 17:59 Effective Meetings 20:38 Customer Engagement Strategies 23:00 Startup Advice 25:37 Navigating a Noisy Market 28:11 Bay Area Mentality 30:31 Career Reflections and AI Impact 33:06 Dealing with Hard Times

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Doug Roseborough

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This episode was published on October 21, 2025.

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