Podcast Advertising Playbook with Heather Osgood

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].

Inside the Mind of a Growth-Focused CMO

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 are evaluating channels like podcast advertising. The conversation dives into what it really takes to build confidence in a medium where the path to purchase is not always linear, and why strong marketing organizations are shifting how they think about attribution, data, and decision-making. In this episode, we cover: * The assumptions CEOs and CMOs still have about podcast advertising * Why so much marketing advice sounds good but rarely gets implemented * How AI is beginning to reshape marketing strategy and execution If you’re navigating how to prove the value of podcast advertising, or looking to better understand how top marketing leaders evaluate performance-driven channels, this episode offers a clear and practical perspective on what actually drives growth. 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].

Live from SXSW: How AI Agents Are Reshaping Podcast Operations with Podstock

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 face today and where automation can actually make a meaningful impact. Rather than replacing teams, tools like Podstock Agent are designed to streamline workflows, reduce manual tasks, and unlock more strategic thinking across podcast networks, studios, and sales organizations. In this episode, we cover: * The problem Podstock set out to solve and why AI became the answer * What Podstock Agent actually does and how it changes day-to-day workflows * The most time-consuming podcast tasks that can now be automated * How AI is shifting the economics and scalability of podcast businesses * Where podcast teams should start when adopting AI tools If you’re thinking about how to scale your podcast business more efficiently, or want a clearer understanding of where AI fits into the industry, this episode offers a grounded, practical look at what’s already possible. This episode was recorded during Podcast Movement Evolutions at SXSW with the support of Nomono, SimpleCast, and The Podcast Academy. 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].