Mentorship, Connection, and Playing the Long Game

Security Chipmunks

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Discover how to navigate the complex landscape of cybersecurity careers with Fletus Poston III, Senior Manager for Security Operations at Crash Plan. Drawing from his diverse background spanning regulated utilities, financial services, and software development since 2007, Fletus shares transformative insights about finding your place in the security ecosystem.
The conversation challenges conventional wisdom about breaking into cybersecurity, with Fletus presenting a compelling metaphor: "Security is like a city" with diverse roles from entry-level positions to executive leadership. Rather than fixating solely on offensive security roles, he encourages newcomers to explore various disciplines to find their perfect fit, whether in SOC analysis, governance, or offensive security.
What truly sets this episode apart is Fletus's counter-intuitive approach to career advancement. Instead of mass-applying to positions, he advocates for a strategic "long game" - identifying target companies, building relationships with their employees over time, and positioning yourself as a knowledgeable peer rather than just another applicant. This approach leverages the power of internal references, dramatically increasing your chances of success.
The discussion delves into the often-overlooked human elements of security, from establishing effective mentorship relationships to implementing practical safeguards against emerging threats like AI voice scams and deepfakes. Fletus shares actionable advice for creating secure password practices and verification techniques that protect against sophisticated social engineering.
Whether you're just starting your cybersecurity journey or looking to advance to the next level, this episode delivers practical wisdom from someone who's navigated the field's challenges firsthand. Remember Fletus's parting advice: "You add value to every room that you enter," and approach security problems with perspective and understanding rather than simply saying "no."
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Chapters

1. Mentorship, Connection, and Playing the Long Game (00:00:00)

2. Welcome to Security Chipmunks (00:00:04)

3. Meet Flitas: Diverse Security Background (00:00:24)

4. Breaking Into Cybersecurity (00:02:25)

5. Competitive Advantage: The Long Game (00:04:16)

6. Value of Mentorship and Connections (00:07:55)

7. Human-Centric Security Approach (00:14:16)

8. Combating AI Voice Scams (00:17:33)

9. Final Thoughts: You Have Value (00:24:22)