Episode 111

full
Published on:

9th Jul 2025

111: From Agency Hustle to CMO Truth Teller: Building Brands, Teams, and Backbone - with Natalie Cunningham, 2x SaaS CMO

In this episode of Women in B2B Marketing, host Jane Serra sits down with Natalie Cunningham, a two-time SaaS CMO, former agency leader, and one of LinkedIn’s most refreshingly honest voices in marketing.

Natalie’s journey from rural Tennessee to the C-suite is packed with lessons on resilience, leadership, and pushing past “professional” expectations. She opens up about what it really means to step into a CMO role, lead through rebrands, and advocate for yourself—without shrinking your voice.

Jane and Natalie explore:

  • The real difference between being a VP and a CMO (beyond the title)
  • How to lead with honesty and impact, even when it comes with risk
  • Why rebrands fall apart after the “fun part”—and how to avoid it
  • The power of healthy conflict and treating peers as your first team
  • How being vocal on LinkedIn can cost you... and why it’s still worth it
  • Why “managing a team is like parenting” is a tired (and harmful) trope
  • The importance of community when you’re the only woman in the room

Key Links:

Guest: Natalie Cunningham: https://www.linkedin.com/in/nataliercunningham/

Host: Jane Serra: https://www.linkedin.com/in/janeserra/


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About the Podcast

Women in B2B Marketing
A weekly podcast dedicated to motivating marketers at all levels in their careers through real-life stories. Our goal is to inspire listeners to achieve more, strive for success, and feel a sense of understanding and community.
Women in B2B Marketing is a weekly podcast dedicated to motivating marketers at all levels in their careers through real-life stories of victory and defeat, challenge and triumph. Our goal is to inspire listeners to achieve more, strive for success, and feel a sense of understanding and community.

This is a place where CMOs, VPs of Marketing, and all strong women B2B marketing leaders discuss their top tactics, strategies, and tips for building teams, leveraging trends, and ultimately rocking their marketing careers - however that looks to them.

Leading marketing teams everywhere from fortune 500s to startups and challenger brands, these women share their stories of rising to the top - and how they overcame any obstacles that came their way.

Made by and for women, insightful for all.

Podcast Host: Jane Serra, 17+ years in B2B marketing across all industries from SaaS to Marketing Agencies and International Outsourcing.

LinkedIn: https://www.linkedin.com/in/janeserra/

Instagram: https://www.instagram.com/womeninb2bmarketing/
Twitter: https://twitter.com/womeninb2bmktg

About your host

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Jane Serra