#135 Unleashing Your Voice: Rising in Sales with Cherilynn Castleman

2B Bolder Podcast : Career Insights & Advice from Successful Women in Business & Tech

What does it take to succeed in male-dominated fields? Cherilynn Castleman knows firsthand, having navigated 30+ years in sales leadership at Fortune 500 companies as a woman of color. Her journey from selling Girl Scout cookies to coaching C-suite executives at Amazon and Walmart reveals powerful insights about career advancement, personal branding, and overcoming barriers.
Cherilynn's revelation that "sales is a gateway skill" transforms how we think about this crucial capability. "Everybody sells," she explains. "If you're interviewing for a job, you're selling yourself. If you have an idea in marketing, you're selling your idea." This reframing makes sales accessible to everyone—especially women who might otherwise avoid this traditionally male-dominated field.
The conversation takes a powerful turn when Cherilynn shares her framework for handling microaggressions—those painful "paper cut" moments that undermine confidence. She outlines three distinct types and exactly how to respond to each, providing practical tools for self-advocacy while maintaining dignity. Her three-part formula for career success is equally actionable: be competent ("too good to be ignored"), have confidence to share your point of view, and genuinely care about your work and clients.
Perhaps most valuable is Cherilynn's strategic approach to mentorship and building a personal brand that attracts opportunities. She reveals that 100% of her business coaching Fortune 500 executives comes through LinkedIn, a platform she once feared, and shares exactly how she transformed her presence there. Her mission to empower one million women by 2030 demonstrates how an audacious goal can focus your efforts and open unexpected doors, from teaching at Harvard to developing global training programs.
Connect with Cherilynn on LinkedIn and mention this podcast to receive her frameworks on any topic discussed. Whether you're early in your career or looking to break through to leadership, her practical wisdom will help you find your voice and show up bolder in every professional setting.
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1. Welcome to To Be Bolder (00:00:00)

2. Discovering Sales as a Gateway Skill (00:02:11)

3. Navigating Microaggressions in Your Career (00:08:26)

4. Finding Your Voice and Speaking Up (00:16:28)

5. Building Your Personal Brand (00:22:41)

6. Mission to Empower One Million Women (00:31:10)