Podcast Advertising Playbook with Heather Osgood

The Next Era of Podcast Creation

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 podcasts are emerging now, and what problems they solve for creators and media companies * The balance between human creativity and AI execution in modern content production * How Inception Point approaches accuracy, discoverability, and avoiding a flood of “good enough” content * The evolving conversation around ownership, IP, and breakout AI-generated personalities * What AI-native podcasting could mean for advertisers, audience targeting, and dynamic listener experiences From production economics to authenticity in advertising, this conversation explores how podcasting may evolve as AI becomes part of the creative process. See Privacy Policy at https://art19.com/privacy [https://art19.com/privacy] and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info [https://art19.com/privacy#do-not-sell-my-info].

Podcast Search Optimization and the Future of Discoverability

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 competitive landscape. The conversation also dives into Ausha’s recent collaboration with Edison Research analyzing the Top 50 podcasts and what the industry can learn from the metadata, publishing habits, and discoverability strategies of top-performing shows. They also discuss: * What Podcast Search Optimization actually means * Why discoverability is becoming more solvable in 2026 * Trends in listener behavior that matter for podcasters and advertisers * What today’s top podcasts are doing differently * The future of podcast intelligence and analytics tools If you’re thinking about podcast growth, audience development, or the future of podcast marketing, this episode offers a valuable look at where the industry is headed next. See Privacy Policy at https://art19.com/privacy [https://art19.com/privacy] and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info [https://art19.com/privacy#do-not-sell-my-info].

Smarter Podcast Inventory Starts Here with Frequency & Flightpath

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 opportunities, and build stronger long-term campaigns. Pete and Sean unpack how the new integration between Frequency and Flightpath aims to solve some of the industry’s biggest operational and revenue challenges while creating a more connected ecosystem for buyers and sellers. In this episode, we cover: * Why unsold podcast inventory remains such a major industry challenge * How predictive planning and forecasting are changing campaign strategy * The shift from simply filling ad spots to managing long-term yield and opportunity * What greater transparency and centralized marketplaces could mean for advertisers and publishers * How the industry can balance automation and efficiency with the long-term value of host-read advertising If you’re interested in where podcast advertising operations, planning, and monetization are headed next, this is an episode you won’t want to miss. See Privacy Policy at https://art19.com/privacy [https://art19.com/privacy] and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info [https://art19.com/privacy#do-not-sell-my-info].

The Signals Shaping Podcast Advertising in 2026

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 within audio, and why podcasting continues to command consumer attention despite remaining dramatically underfunded in media budgets. The conversation also explores the limitations of legacy planning approaches, including genre-based buying and overreliance on promo codes, while examining how signal-informed planning is helping advertisers make smarter, more strategic decisions. Heather and the Magellan team discuss: • Why podcasting delivers unique reach even within audio campaigns • What advertisers miss when they rely solely on genre targeting • How market intelligence can uncover hidden revenue and reactivation opportunities • The evolving role of pixel-based attribution in podcast measurement • How advertisers are using competitive spend data to inform strategy Whether you’re a brand, agency, publisher, or podcast creator, this episode offers a deeper look at the data shaping the next era of podcast advertising. If you're interested in exploring the guide, you can find it here: https://info.truenativemedia.com/guide-beyond-the-buy?hs_preview=xyvSwHAl-212093555242 See Privacy Policy at https://art19.com/privacy [https://art19.com/privacy] and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info [https://art19.com/privacy#do-not-sell-my-info].

Building in a Regulated Space: What Kids & Family Podcasting Teaches Us About Advertising

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 regulated category, and why the kids and family space may be one of the most overlooked opportunities in podcast advertising today. * Why advertisers have historically shied away from kids and family podcasting * The realities of building an ad-supported network in a regulated environment * How to position podcast advertising to brands used to digital and social channels * What performance metrics actually resonate in this category * Where the biggest opportunities lie for podcast advertising in the next 3–5 years If you’ve ever wondered how podcast advertising works in more complex categories or where untapped opportunity might exist, this episode offers a thoughtful look at what’s possible. See Privacy Policy at https://art19.com/privacy [https://art19.com/privacy] and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info [https://art19.com/privacy#do-not-sell-my-info].