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

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

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

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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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