Podcast Advertising Playbook with Heather Osgood

Hosted by Heather Osgood

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225

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Jun 2026

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June 10, 202645 min

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 companiesThe balance between human creativity and AI execution in modern content productionHow Inception Point approaches accuracy, discoverability, and avoiding a flood of “good enough” contentThe evolving conversation around ownership, IP, and breakout AI-generated personalitiesWhat AI-native podcasting could mean for advertisers, audience targeting, and dynamic listener experiencesFrom 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 and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

May 27, 202639 min

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 meansWhy discoverability is becoming more solvable in 2026Trends in listener behavior that matter for podcasters and advertisersWhat today’s top podcasts are doing differentlyThe future of podcast intelligence and analytics toolsIf 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 and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

May 13, 202643 min

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 challengeHow predictive planning and forecasting are changing campaign strategyThe shift from simply filling ad spots to managing long-term yield and opportunityWhat greater transparency and centralized marketplaces could mean for advertisers and publishersHow the industry can balance automation and efficiency with the long-term value of host-read advertisingIf 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 and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

May 6, 202637 min

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 strategyWhether 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-212093555242See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

April 29, 202641 min

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 podcastingThe realities of building an ad-supported network in a regulated environmentHow to position podcast advertising to brands used to digital and social channelsWhat performance metrics actually resonate in this categoryWhere the biggest opportunities lie for podcast advertising in the next 3–5 yearsIf 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 and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

April 15, 202645 min

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 and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

April 1, 202626 min

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 and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

March 18, 202649 min

Beyond Downloads: Rethinking Podcast Measurement

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 downloads alone fall short and how consumption data provides a clearer view of performance Where impressions fit and what better reporting should look like for advertisers today Why podcast retention and ad engagement are still undervalued and under-communicated What’s ahead for the industry, including collaboration, video integration, and AI’s impact on creative If you’re looking to better understand how measurement is evolving and what it means for your podcast advertising strategy, this episode offers a clear and practical perspective on where the industry is headed.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

March 4, 202631 min

The Power of the Middle

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 access podcast inventory at scale. Together, he and Heather unpack the assumptions that often drive media planning decisions, why advertisers tend to focus on top-ranked shows, and what brands may be missing when they overlook mid-tier creators and niche audiences. In this episode, we discuss: • Why mid-tier and long-tail podcasts are often undervalued in media plans despite strong audience alignment • How programmatic buying is making it easier for advertisers to scale across a broader range of podcasts • Whether the concept of “mid-tier” podcasts will evolve as buying and execution become more automated If you are looking for smarter ways to scale podcast campaigns while maintaining strong audience alignment, this episode offers a thoughtful look at how expanding beyond the top charts could unlock meaningful performance and reach.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

February 18, 202642 min

Attribution in the Age of Audio and Video

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 appear lower than expected, and how advertisers can think more strategically about evaluating performance across platforms like Spotify Video, YouTube, and traditional audio. In this episode, we discuss: How podcast attribution has improved and what is driving greater advertiser confidence What advertisers often misunderstand about podcast measurement and performance data The tradeoffs that come with video podcasting and how it impacts reporting How to think about attribution when campaigns run across audio, Spotify Video, and YouTube What “good enough” attribution looks like and what the future of measurement may hold If you are trying to better understand podcast performance and make smarter decisions with attribution data, this episode offers practical guidance and a clear view of where the industry is headed.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.