Doug Roseborough

Doug Roseborough

Author: Evan McCann October 21, 2025 Duration: 36:40

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


Evan McCann sits down with the people shaping Canada's business landscape, moving past the polished success stories to get into the real work that happens behind the scenes. The Hard Part with Evan McCann is built on conversations with founders, investors, and leaders who have navigated unique challenges, focusing on the pivotal decisions and often overlooked struggles that define a venture. This podcast explores the specific strategies and personal playbooks that have driven impact, offering a rare look at the operational truths of building something significant. While the spotlight frequently falls on innovators elsewhere, these episodes are dedicated to the Canadian visionaries whose work is redefining global entrepreneurship from here at home. You'll hear candid reflections on risk, resilience, and the moments that tested their conviction, providing not just inspiration but tangible insight into the mechanics of leadership and growth. Each discussion aims to unpack the nuance of achievement, making it an essential listen for anyone curious about the substance behind the headlines in the Canadian business world.
Author: Language: en-ca Episodes: 100

The Hard Part with Evan McCann
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