Latest Episode

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 s...

Recent Episodes

Smarter Podcast Inventory Starts Here with Frequency & Flightpath
May 13, 2026

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 s...
The Signals Shaping Podcast Advertising in 2026
May 6, 2026

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, a...
Building in a Regulated Space: What Kids & Family Podcasting Teaches Us About Advertising
April 29, 2026

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 lead...
Inside the Mind of a Growth-Focused CMO
April 15, 2026

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 c...
Live from SXSW: How AI Agents Are Reshaping Podcast Operations with Podstock
April 1, 2026

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 t...
Beyond Downloads: Rethinking Podcast Measurement
March 18, 2026

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 ...

About the Host

HEATHER OSGOOD Profile Photo
HEATHER OSGOOD

Founder

Heather Osgood is the founder of True Native Media, a boutique podcast representation agency specializing in podcast advertising. With an extensive background in radio advertising and a love for podcasting, Heather was uniquely positioned to start an agency that could help advertisers get better results and assist podcasters in finding sponsors.

She is an influential voice in the podcast advertising space and has sold over 60K ads in six years. Heather is also the Podcast Moneymaker's creator, a course designed for podcasters who want the formula, tools, and tactics to get advertisers in 6 weeks.

Heather can be credited for contributing her expertise to major podcasting events like Podcast Movement, PodFest, and more. She is the host of The Podcast Advertising Playbook, a show dedicated to educating anyone interested in podcast advertising.

When Heather is not playing matchmaker to brands and podcasts, you will find her hiking and spending time with her family at the beach.