Podcast Advertising Playbook with Heather Osgood

Hosted by Heather Osgood

Business

Website RSS feed

Episodes

230

Latest episode

Aug 2026

Language

Listen to episodes

60 recent

September 2, 202650 min

Are We Trying Too Hard? Laura Mayer on Podcasting’s Next Chapter

Laura Mayer has spent her career inside some of podcasting’s most influential companies. Now, she’s looking back at the ambition, anxiety, and relentless drive that came with building a career in a fast-moving industry. In this episode, Heather sits down with Laura, podcast executive and author of Tryhard: A Cautionary Tale of Clocking In and Spinning Out , to talk about what happens when professional ambition becomes impossible to turn off, and what she learned when she finally did. They also take a candid look at where podcasting stands today: the industry’s obsession with video, what audio lovers should actually be worried about, what the business still isn’t paying enough attention to, and whether podcasting has outgrown some of the culture that defined its early years. It’s a conversation about ambition, burnout, podcasting’s identity crisis, and figuring out what success looks like when you stop trying quite so hard. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

August 20, 202652 min

Who Defines the Future of Podcast Advertising?

Podcasting is evolving faster than the systems built to measure it. Audiences are moving between audio and video, consumption is increasingly happening across closed platforms, and advertisers are being asked to make sense of performance without always having access to the full picture. In this episode of The Podcast Advertising Playbook , Heather Osgood sits down with Dan Granger, CEO and Founder of Oxford Road, to unpack the newly released AMP Accords (Alliance for Measurement in Podcasting) and the larger questions they raise for the future of podcast advertising. They explore what actually qualifies as a podcast in an increasingly video-first world, who should own podcast budgets inside major brands, and what happens when audiences migrate to platforms where measurement and attribution work very differently. At the center of the conversation is a bigger question: As podcasting evolves, can the advertising ecosystem evolve with it? Heather and Dan examine what greater industry alignment could look like, what advertisers need from platforms like Apple, Spotify, and YouTube, and whether the push toward video could fundamentally change how podcast advertising is bought, measured, and valued. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

August 5, 202641 min

How Smart Advertisers Actually Measure Podcast Performance

Podcast advertising has matured, but measurement is still one of the most misunderstood aspects of the industry. In this episode of The Podcast Advertising Playbook , Heather Osgood sits down with Jason Fialkov, Vice President of Sales at Claritas, to unpack how marketers should really be evaluating podcast performance in today's privacy-first landscape. Together, they explore the biggest misconceptions surrounding podcast attribution, the difference between downloads, conversions, and true business impact, and whether traditional tools like promo codes and vanity URLs still have a place alongside more advanced measurement solutions. They also discuss why YouTube can't be measured the same way as audio podcasts, how evolving privacy regulations and the loss of third-party cookies are reshaping attribution, and what today's data reveals about podcasting's ability to drive both brand awareness and lower-funnel results. Finally, Jason shares his perspective on how AI will transform campaign measurement over the next several years and the one piece of advice every CMO should hear before investing in podcast advertising. Whether you're a brand, agency, or creator looking to better understand podcast effectiveness, this episode offers a practical framework for measuring what actually matters. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

July 22, 202638 min

What Global Advertisers Know About Podcasting That the U.S. Is Missing

Podcast advertising is growing around the world, but not every market is evolving in the same way. In this episode of The Podcast Advertising Playbook , Heather Osgood sits down with Adel Saadi, Founder & Managing Director of Next Broadcast Media, to explore how brands and agencies are approaching podcast advertising across international markets. Together, they discuss the biggest shifts shaping the industry, the balance between host-read and programmatic advertising, the role AI is beginning to play, and the metrics that matter most to today's advertisers. Adel also shares the misconceptions he still hears from marketers, where agencies continue to add value in an increasingly automated landscape, and one prediction about the future of podcast advertising that may surprise even industry insiders. Whether you're a brand, agency, or creator, this conversation offers a broader perspective on where podcast advertising is headed—and what you can learn from markets beyond the U.S. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

July 8, 202640 min

The SEO & Content Marketing Gap Killing Your Podcast Growth

Podcast discovery is changing rapidly, and creators who understand how audiences find content will be better positioned to grow in the years ahead. In this episode, Heather sits down with Andrea De'Marsi, Founder and CEO of PodSEO, to discuss how podcast search has evolved, why traditional podcast platforms weren't built as search engines, and what that means for creators looking to reach new listeners. They explore the most common discoverability mistakes podcasters make, practical SEO strategies that can increase organic growth, the metrics that actually matter, and how stronger discoverability can improve advertising performance and sponsorship opportunities. The conversation also examines AI's growing role in podcast search and why independent creators have more opportunities than ever to compete alongside larger networks. Whether you're launching a new show or looking to grow an established one, this episode offers practical insights into building long-term visibility in an increasingly searchable podcast ecosystem. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

June 24, 202639 min

Podcasting’s Next Growth Engine: How Local and Regional Advertisers Are Entering the Space

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 targeting, and inventory access are making podcast advertising more accessible than ever before, while examining what this shift means for creators, advertisers, and the industry as a whole. In this episode, you'll learn: What's changed most in programmatic podcast advertising over the past two years Why local and regional advertisers are increasingly investing in podcasting How expanded inventory and scale are helping unlock new advertising budgets Which advertiser categories are entering the space for the first time How podcasting can balance programmatic efficiency with the authenticity listeners value Whether you're a creator, advertiser, agency professional, or industry observer, this conversation offers valuable insight into one of the most important growth opportunities shaping the future of podcast advertising. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

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