The Hard Part with Evan McCann

← The Hard Part with Evan McCann21 oct 2025 · 37 min

Doug Roseborough

Doug Roseborough21 oct 202537 min

<p><a href="https://www.linkedin.com/in/dougroseborough/" target="_blank" rel="noopener noreferer"><strong>Doug Roseborough</strong></a> spent his career at multiple leading technology companies including 30 plus years at Oracle.</p><p><br></p><p><strong>Chapters</strong></p><p>00:00 Intro</p><p>1:40 Early Days at Oracle</p><p>02:56 Oracle&#39;s Secret Sauce</p><p>05:16 Transition to the Bay Area</p><p>08:15 Rolling Out Pricing Models</p><p>10:31 Cultural Insights at Oracle</p><p>13:05 Leadership and Team Dynamics</p><p>15:35 Operations at Oracle</p><p>17:59 Effective Meetings</p><p>20:38 Customer Engagement Strategies</p><p>23:00 Startup Advice</p><p>25:37 Navigating a Noisy Market</p><p>28:11 Bay Area Mentality</p><p>30:31 Career Reflections and AI Impact</p><p>33:06 Dealing with Hard Times</p>