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2B Bolder Podcast : Career Growth and Insights from Women in Business, Tech & Sports
The 2B Bolder Podcast brings you into real conversations with women leaders in business, tech, and sports. Going deep into what helped them succeed, shine and stand out as leaders.
Hosted by Mary Killelea, a former Intel marketing strategist and career visibility coach, the show shares real stories and practical insights from women who have built meaningful careers and leadership paths.
Each conversation provides guidance on:
• Building your personal brand with intention
• Speaking with confidence and clarity
• Strengthening leadership presence and influence
• Navigating career transitions with purpose
• Advocating for your value in rooms where decisions are made
If you’ve ever felt overlooked despite the work you deliver, this podcast will help you show up, speak up, and step forward — with clarity, confidence, and a strong sense of who you are.
Learn more at www.2BBolder.com
The 2B Bolder Podcast ranks in the top 3% of 3.5 million podcasts globally (Listen Score).
2B Bolder Podcast : Career Growth and Insights from Women in Business, Tech & Sports
#135 Unleashing Your Voice: Rising in Sales with Cherilynn Castleman
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.
See the full library of Women in Business and Tech Career podcasts
Cherilynn Castleman's Career Tips for Women Transcript
The 2B Bolder Podcast provides first-hand access to some amazing women. Guests will include women from leading enterprise companies to startups, women execs, coders, account execs, engineers, doctors, and innovators.
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