oleary-portugal-portrait copy.jpg


I am a media advisor and consultant and former executive, journalist, and digital strategist. I am currently consulting for a range of media and journalism startups looking to sharpen their strategic focus, prepare for launch, and bring new projects to life.

Previously, I lead content at Headspace, launching Sleep by Headspace — a highly successful, unique sleep experience created through a human-centered design sprint process. Prior to that, I served as the Chief Story Officer & Editorial Director for Upworthy leading the site through a strategic reinvention in original storytelling in text and video.  

From 2007 to 2014, I worked for The New York Times in a range of roles as a reporter, a multimedia producer, a digital editor for news with a particular focus on print-digital newsroom integration. In 2014, I was on the team that wrote the New York Times's Innovation Report, heralded by Nieman Lab as one of the "key documents of this media age."  

I learned the art of storytelling as a producer for This American Life and early intern at Radiolab. My first real job was as a reporter for a small town newspaper.

I am currently based in Venice, California.