Podcast Advertising Playbook with Heather Osgood

For years, podcast advertising has been largely driven by national brands. But that is beginning to change.

In this episode of The Podcast Advertising Playbook, Heather Osgood sits down with Scott Porretti, President of Katz Digital, to discuss how programmatic advertising is expanding podcasting's reach and opening the door for local and regional advertisers.

Together, they explore how advancements in buying technology, audience tar...

Artificial intelligence is rapidly reshaping the media landscape, but what does that actually mean for podcasting? On this episode of The Podcast Advertising Playbook, Heather sits down with Jeanine Wright, Co-Founder & CEO of Inception Point and former executive at Simplecast, AdsWizz, and Wondery, to unpack what AI-generated audio could mean for creators, advertisers, and the future of content itself.

• Why AI-generated podc...

This week on The Podcast Advertising Playbook, Heather Osgood sits down with Jennifer Han, CMO at Ausha, to explore why podcast discoverability remains one of the industry’s biggest challenges and why that may finally be starting to change.

Jennifer breaks down the rise of Podcast Search Optimization (PSO), how listener behavior is evolving, and why publishers need to rethink growth strategies in today’s increasingly com...

This week on The Podcast Advertising Playbook, Heather Osgood sits down with Pete Jimison, CEO of Frequency, and Sean Howard, CEO of Flightpath Software, to discuss how predictive intelligence, centralized marketplaces, and smarter inventory management are reshaping podcast advertising.

As podcasting continues to mature, publishers and advertisers alike are looking for more efficient ways to forecast inventory, reduce unsold opportu...

In this episode of The Podcast Advertising Playbook, Heather Osgood sits down with the team at Magellan AI to unpack the insights behind Beyond the Buy: Smarter Podcast Advertising for 2026, a new guide exploring how data, attribution, and market intelligence are reshaping the future of podcast advertising.

Together, they dive into why podcast audiences and streaming audiences behave differently, what incremental reach really means ...

In this episode of The Podcast Advertising Playbook, host Heather Osgood sits down with Jed Baker, former CEO of Starglow Media and now Head of Audio at SuperAwesome.

Jed shares the story behind building Starglow into a leading kids and family podcast network, and what ultimately made its acquisition by SuperAwesome the right strategic move. The conversation dives into the unique challenges and opportunities of operating in a highly...

In this episode of The Podcast Advertising Playbook, host Heather Osgood sits down with Rich Smith, Founder of Rich M Smith Growth Studio, to unpack what today’s most effective marketing leaders actually care about when it comes to growth and performance.

From the disconnect between marketing buzzwords and real-world execution to the increasing pressure on teams to prove results, Rich shares a candid look at how CEOs and CMOs ...

In this special live episode of The Podcast Advertising Playbook, recorded at Podcast Movement Evolutions during SXSW, host Heather Osgood sits down with the team behind Podstock to explore how AI is beginning to transform the way podcast businesses operate.

From the origin story of Podstock to the development of their new AI-powered “Agent,” this conversation dives into the real operational challenges podcast teams fac...

In this episode of The Podcast Advertising Playbook, host Heather Osgood sits down with Jonas Woost, Co-Founder of Bumper, to explore how podcast measurement is evolving beyond traditional metrics.

Jonas shares how shifting from downloads to deeper consumption data can unlock more accurate insights, helping advertisers and publishers make smarter decisions and build stronger campaigns.

In this episode, we cover:

• Why downloa...

In this episode of The Podcast Advertising Playbook, host Heather Osgood sits down with Brian Conlan, President of DAX US, to explore how programmatic buying is reshaping the podcast advertising landscape and why mid-tier and long-tail podcasts may represent one of the most overlooked opportunities in the medium.

Brian shares how he entered the podcast space and offers insight into the role DAX US plays in helping advertisers acces...

In this episode of The Podcast Advertising Playbook, host Heather Osgood sits down with Bryan Barletta, Founder of Sounds Profitable, to discuss how podcast attribution has evolved and what measurement really looks like in a world where audio and video are converging.

Attribution in podcasting has come a long way, but it is still widely misunderstood. Bryan shares where measurement is genuinely improving, why some reporting may app...

On this episode of the Podcast Advertising Playbook, Heather Osgood sits down with Marty Avallone, CEO of Ekoz AI, to explore the growing conversation around AI-generated, voice-cloned host-read ads in podcast advertising.

Marty shares his background and what inspired him to build Ekoz AI, along with a look at how voice cloning is currently being used in live campaigns. Together, they discuss where this emerging format fits within ...

To mark 10 years of True Native Media, VP Nick Gryniewicz steps in as guest host to sit down with founder and CEO Heather Osgood for an honest conversation about what it really takes to build a company in podcast advertising from the ground up.

Together, they reflect on the lessons learned over a decade in business, the pivotal moments that shaped True Native Media’s growth, and the decisions that changed everything along the...

In this episode of The Podcast Advertising Playbook, host Heather Osgood sits down with Jason Fishman, Co-Founder and CEO of Digital Niche Agency (DNA), to explore how specialization, podcasting, and thoughtful marketing strategy can drive sustainable growth. Jason shares how building a focused niche helped DNA stand out in a crowded digital landscape and why clarity matters more than ever as AI and automation reshape the industry.

In this episode of The Podcast Advertising Playbook, host Heather Osgood sits down with Sam Brake Guia, Co-Founder of Podwritten and host of Mics to Millions. Sam works at the center of podcast guesting, booking, and creator strategy, bringing a unique view into how brands and personalities can use interviews to increase visibility and connect with targeted audiences.

Together, Heather and Sam explore:

• Why certain industries...

This week, host Heather Osgood sits down with Steve Rock, a leader in the influencer and creator marketing space, for a conversation that bridges two worlds advertisers often treat as separate: podcasting and influencer marketing. With deep experience across both industries, Steve brings a grounded, strategic perspective on how brands can think more holistically about creator-led media.

In this episode, Heather and Steve explore wh...

In this episode of The Podcast Advertising Playbook, host Heather Osgood sits down with Matt Drengler, Head of Partnerships at Podscribe, to explore one of the hottest questions in the industry today: how video is changing podcast advertising.

Together, they unpack what the data says about video ad performance versus traditional audio-only campaigns, how engagement and attribution differ between the two formats, and what advertiser...

In this episode of The Podcast Advertising Playbook, host Heather Osgood sits down with Greg Glenday, CEO of Acast, the world's largest independent podcast company. These two industry experts talk about growth, monetization and expansion, and how podcasts are leading the charge in innovative advertising.

Tune in to hear:

• How Acast supports creators and advertisers from start to finish
• How global expansion is helping adve...

In this episode of The Podcast Advertising Playbook, host Heather Osgood shares why choosing shows by category isn't the best advertising strategy, and what to do instead.

In this episode, you will hear:

• Why choosing shows by category often falls short
• How shows within the same category can yield vastly different results
• What to look for instead: demographics, psychographics and more
• Tools to help you target your aud...