Olivia Oshry - CMO, OAAA

Digital & Dirt

Digital & Dirt
Olivia Oshry - CMO, OAAA
Mar 18, 2026
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In this week’s episode of the Digital and Dirt podcast, Ian sits down with Olivia Oshry, CMO of the OAAA, to discuss her career, the evolution of media, and why the OAAA is redefining Out of Home as the “Human Medium.”

Podcast Breakdown: 

00:00 - 06:30 Meet Olivia Oshry
06:31 - 09:30 Exploration, Internships & Career Discovery
09:31 - 13:06 Entering Digital Media & AOL beginnings
13:07 - 16:30 Mentorship, Growth & Early Lessons
16:31 - 20:54 Building Experience & Navigating Opportunities
20:55 - 24:30 OOH landscape & Creative Evolution
24:31 - 29:00 Industry Shifts & Changing Media Landscape
29:01 - 01:01:37 Career Reflections & Industry Perspective