Heather Osgood: Podcast Advertising, Then and Now

On this special edition of Podcast Insider, Todd Cochrane, CEO of Blubrry Podcasting, sat down with Heather Osgood, founder of True Native Media, to discuss the evolution and current landscape of podcast advertising. With a rich background in ad sales and entrepreneurship, she has been at the forefront of connecting podcasters with advertisers for nearly a decade.

Heather launched True Native Media nine years ago with the mission to represent independent podcasters. At the time, most agencies only worked with shows that had thousands and thousands of downloads per episode. Heather saw untapped potential in smaller shows and proved otherwise to the market, successfully selling ads on more modestly sized podcasts.

“I started the company really to service the independent creator,” she explained. “At that time, you had to have 50,000 downloads per episode to get representation. I knew I could sell podcasts that were smaller than that.”

While her agency now partners with larger shows as well, her initial goal to empower indie creators continues to resonate.

The Rise of Dynamic and Programmatic Ads

A central theme in Heather and Todd’s conversation was the shift from embedded to dynamic ad insertion. In the early days, ads were baked into episodes permanently, which limited their flexibility. Today, dynamic ad insertion allows ads to be swapped in and out across an entire catalog. This has made smaller shows more attractive to advertisers, enabling higher overall impression counts and better campaign scalability.

“With dynamic ad insertion, we can serve a much larger number of impressions,” Heather noted. “An advertiser can come to us, and we might say, ‘This show has 10 to 15,000 unique listeners, but we can serve you 50,000 impressions over 30 days.’ That really has helped us.”

Programmatic advertising has also taken center stage. Osgood highlighted that while CPMs (cost per thousand impressions) in programmatic campaigns may not reach the heights of direct host-read ads, the trade-off in convenience and predictability is significant. Many podcasters value the “set-it-and-forget-it” nature of programmatic ads, especially when those earnings cover production costs or fund growth strategies.

Attribution, Brand Safety, and Targeting

With the growing sophistication of podcast ad tech, attribution and brand safety have become top priorities. Heather emphasized the importance of pixel tracking, noting that it has become a non-negotiable for many advertisers.

“Having pixel tracking is more important than anything else,” she said. “Advertisers don’t really care where the results are coming from—they just care that the results are there. And the pixel can prove that.”

Brand safety tools also help ensure that ads align with show content, offering contextual targeting and geotargeting options, especially crucial for programmatic ad buys.

The Video Conundrum

Todd and Heather also tackled the ongoing discussion between audio and video in podcasting. While video podcasts and simulcasts are gaining popularity, Heather cautioned against abandoning audio.

“Audio is still superior to video in the podcast space from an advertising perspective,” she stressed. “There’s a huge push to video, but we can’t lose sight of the fact that we are an audio platform.”

Advertisers continue to show stronger interest in audio inventory, and listener engagement tends to be deeper, especially with retention rates around 80%. Meanwhile, YouTube viewership can be unpredictable — some videos explode in popularity while others stagnate.

A Dual Strategy for Monetization

Ultimately, Heather advocates for a hybrid model combining direct host-read ads with programmatic placements. This dual strategy allows podcasters to maximize revenue without sacrificing listener experience. For those just starting out or operating on smaller budgets, programmatic can be a lifeline—one that not only offsets costs but also incentivizes growth.

As podcasting continues to mature, industry leaders like Heather Osgood and Todd Cochrane are helping creators navigate the evolving ecosystem. One thing remains clear: in podcast advertising, flexibility and innovation are key.