Smashing The Tech Boys’ Club: How Natalie Cunningham Rewrites the Rules of Tech Leadership

What happens when you mix old-school agency experience with zero tolerance for tech bro bullshit?

In this episode of MKTG TLK, we sit down with Natalie Cunningham, a veteran marketer with 15+ years of experience who shares how she navigated everything from ridiculous “women must wear skirts” dress codes to toxic founder dynamics. Natalie breaks down how women can own their career narrative, build genuine relationships without compromising their authenticity, and the changes we need in tech’s male-dominated culture.

About Natalie Cunningham: Natalie Cunningham is a seasoned marketing executive with extensive experience in B2B tech and SaaS. She started her career in agencies, where she partnered with major tech clients and other established industries before transitioning into tech leadership roles. Natalie is known for her advocacy for authentic leadership and is passionate about mentoring other marketing professionals. She actively works to create more equitable opportunities in tech through initiatives like her “open to help” chats.

Short on time? Here are some quick takeaways:

  1. Authenticity Over Conformity: While early career advice often suggests women need to “play the game” and adopt traditionally masculine leadership styles, success can come from being true to your authentic self and leadership style while setting clear boundaries.

  2. The Hidden Impact of Job Requirements: The tech industry’s emphasis on specific years of experience (especially 10+ years) disproportionately affects women who entered the workforce facing systemic barriers and may have had to make career pivots due to workplace challenges

  3. Building Relationships with Purpose: Rather than focusing solely on proving yourself through work output, investing time in genuine relationship-building across teams can create advocates and support networks that enhance your career progression.

Watch the convo →

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Shoutout to Wistia for sponsoring season three of MKTG TLK. Wistia’s complete marketing platform makes video creation, collaboration, and measurement a cinch. Learn more at wistia.com/MKTG.

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Breaking Barriers in Marketing with Kiersti Bird

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The Power of Brand Marketing: Building Emotional Connections with Samantha Goretski