Soulful CXO

Hosted by Soulful CXO

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Oct 2026

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Soulful CXO explores the intersection of technology, business, and humanity. Each episode features a thoughtful conversation with leaders who share real stories about navigating cybersecurity, leadership pressures, and personal growth. Hosted by Dr. Rebecca Wynn, a renowned CISO and cybersecurity expert, the show invites listeners to reflect on how intention, purpose, and values shape the way we lead. Through candid insights and vulnerable moments, guests reveal the challenges they have faced, the lessons they have learned, and the positive impact they strive to make in the world. Website: www.SoulfulCXO.com

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October 6, 2026Episode 855 min

Margaret Hamilton: The Code That Took Us to the Moon

Episode Summary: In this episode of The Soulful CXO, Dr. Rebecca Wynn reflects on the extraordinary work of Margaret Hamilton, the Apollo software engineer who helped land Apollo 11 on the moon. We explore how she built critical, life-dependent systems in an era without modern computing frameworks, insisted on error-proofing when failure wasn't an option, and established software engineering as a legitimate scientific discipline. This is a masterclass in executive conviction, systemic foresight, and leadership that lasts. Episode Highlights: • The core principles of error-proofing and building for worst-case scenarios. • How Margaret Hamilton fought for the validation of software engineering in a male-dominated aerospace arena. • The 1969 Apollo 11 landing: Why prioritizing critical data streams saved the mission. Sponsor Produced in partnership with Click Solutions Group — providing cybersecurity leadership, strategy, and technology solutions for modern enterprises. Learn more: ClickSolutionsGroup.com 🎧 Listen Now Apple Podcasts: https://podcasts.apple.com/us/podcast/soulful-cxo/id1680649397 Spotify: https://open.spotify.com/show/4DJ67GCpreXLgy2VSa5Ire 🔗 Connect on LinkedIn Dr. Rebecca Wynn: https://www.linkedin.com/in/RebeccaWynnCISSP 📘 The Companion Manifesto Look for the forthcoming release of "Hidden Architectures: 12 Blueprints of Trust, Vision, and Soulful Leadership" on Amazon Kindle and print. Hashtags #SoulfulCXO #MargaretHamilton #SoftwareEngineering #Apollo11 #CyberSecurity #Leadership #ExecutiveInsight #RiskManagement #SystemsDesign #CISO

January 27, 2026Episode 8412 min

Privacy by Design: Why Always in Battle Mode

Episode Summary: In this episode of Soulful CXO, Dr. Rebecca Wynn sits down with Dr. Ann Cavoukian, world-renowned privacy expert and creator of Privacy by Design (PbD), as well as Executive Director of the Global Privacy and Security by Design Centre. They discuss: · The principles of Privacy by Design and how it aims to proactively prevent privacy harms. · The challenges posed by AI , smart cities , and data brokers in protecting personal information. · Why CPOs should report directly to the CEO to elevate privacy as a priority within organizations. · How to handle the data privacy challenges presented by emerging technologies like AI and quantum computing . · The importance of encryption , scrubbing personal identifiers , and ensuring data consent for future-proofing privacy. This episode provides essential insights for executives, technology leaders, and privacy advocates committed to securing data in today’s digital world. Sponsor Produced in partnership with Click Solutions Group — providing cybersecurity leadership, strategy, and technology solutions for modern enterprises. Learn more: ClickSolutionsGroup.com 🎧 Listen Now Apple Podcasts: https://apple.co/49vptby Spotify: https://open.spotify.com/show/4DJ67GCpreXLgy2VSa5Ire ✉️ Subscribe to the Soulful CXO Insights Newsletter https://lnkd.in/gY76RASc 📺 Follow the Soulful CXO YouTube Channel https://www.youtube.com/@soulfulcxo 🔗 Connect on LinkedIn Dr. Rebecca Wynn: https://www.linkedin.com/in/RebeccaWynnCISSP Soulful CXO: https://www.linkedin.com/company/soulfulcxo Dr. Ann Cavoukian: https://x.com/AnnCavoukian Dr. Ann Cavoukian : https://www.linkedin.com/in/ann-cavoukian-ph-d-3a78809/ GPS Design Centre : https://gpsbydesigncentre.com/ Resources / References • ISO 31700-1:2023 Privacy by Design for Consumer Goods and Services https://www.iso.org/standard/84977.html Support Buy Me a Coffee Hashtags #SoulfulCXO #Leadership #ExecutiveLeadership #Integrity #Audit #Cybersecurity #RiskManagement #CISO #Privacy #PrivacyByDesign #BusinessEthics #ISO31700 #GDPR

December 9, 2025Episode 8310 min

The Moral Compass of Great Leaders

Episode Summary: In this episode of Soulful CXO, Dr. Rebecca Wynn sits down with Terry Grafenstine, Chief Audit Executive and EVP at Pentagon Federal Credit Union (PenFed) and past Chair of the IIA Global Board of Directors. They discuss: • Leading with integrity and a strong moral compass in high-stakes environments • Balancing risk, relationships, and business realities • Communicating audit and cybersecurity risks to senior executives • Preventing burnout and building resilient teams This episode provides practical strategies for leaders navigating complex decisions while maintaining ethics, performance, and long-term impact. Sponsor Produced in partnership with Click Solutions Group — providing cybersecurity leadership, strategy, and technology solutions for modern enterprises. Learn more: ClickSolutionsGroup.com 🎧 Listen Now Apple Podcasts: https://apple.co/49vptby Spotify: https://open.spotify.com/show/4DJ67GCpreXLgy2VSa5Ire ✉️ Subscribe to the Soulful CXO Insights Newsletter https://lnkd.in/gY76RASc 📺 Follow the Soulful CXO YouTube Channel https://www.youtube.com/@soulfulcxo 🔗 Connect on LinkedIn Dr. Rebecca Wynn: https://www.linkedin.com/in/RebeccaWynnCISSP Soulful CXO: https://www.linkedin.com/company/soulfulcxo Terry Grafenstine: https://www.linkedin.com/in/tgrafenstine/ PenFed: https://www.penfed.org/ Resources / References • Adapting Without Compromising Integrity: A Leadership Lesson in Security & Politics https://www.linkedin.com/pulse/adapting-without-compromising-integrity-leadership-wynn-soulful-cxo-pgpmc/ • How to Be Successful in Navigating a New Organization https://www.linkedin.com/pulse/how-successful-navigating-new-organization-dr-rebecca-qgquc/ Support Buy Me a Coffee Hashtags #SoulfulCXO #Leadership #ExecutiveLeadership #Integrity #Audit #Cybersecurity #RiskManagement #CISO #BurnoutPrevention #Resilience #BusinessEthics #CareerGrowth #WominInTech

August 20, 2024Episode 6430 min

Powerful Strategies for Negotiation Success

Episode Summary: In this episode of Soulful CXO, Dr. Rebecca Wynn sits down with Steven “Cash” Nickerson, Chairman & CEO of Nickerson Stoneleigh, Inc. and WSJ best-selling author. They discuss: • Lifelong learning and engaging the mind to enhance leadership and negotiation skills • Strategies for flipping the script in negotiations and managing complex relationships • Lessons from high-profile cases, including the Elon Musk-Twitter acquisition • Leveraging negotiation as a tool for business success and human connection This episode provides actionable insights for executives, leaders, and professionals looking to elevate their negotiation skills, influence, and business strategy. Sponsor Produced in partnership with Click Solutions Group — providing cybersecurity leadership, strategy, and technology solutions for modern enterprises. Learn more: ClickSolutionsGroup.com 🎧 Listen Now Apple Podcasts: https://apple.co/49vptby Spotify: https://open.spotify.com/show/4DJ67GCpreXLgy2VSa5Ire ✉️ Subscribe to the Soulful CXO Insights Newsletter https://lnkd.in/gY76RASc 📺 Follow the Soulful CXO YouTube Channel https://www.youtube.com/@soulfulcxo 🔗 Connect on LinkedIn / Social Dr. Rebecca Wynn: https://www.linkedin.com/in/RebeccaWynnCISSP Soulful CXO: https://www.linkedin.com/company/soulfulcxo Cash Nickerson: Website: https://cashnickerson.com/ LinkedIn: https://www.linkedin.com/in/stevencashnickerson/ Facebook: https://www.facebook.com/cashnickersonauthor Twitter: https://twitter.com/cashnickerson Resources / References • The 7 Tensions of Negotiation — https://www.amazon.com/7-Tensions-Negotiation-Cash-Nickerson/dp/1641468505/ • Navigating Ethics in Cybersecurity — https://www.linkedin.com/pulse/navigating-ethics-cybersecurity-dr-rebecca-wynn-soulful-cxo-s02tc/ Support Buy Me a Coffee: https://www.buymeacoffee.com/soulfulcxo Hashtags #SoulfulCXO #Leadership #ExecutiveLeadership #Negotiation #CareerGrowth #ProfessionalDevelopment #BusinessStrategy #Influence #TeamBuilding #Resiliency

April 3, 2023Episode 228 min

How to Build Trust and Set Boundaries

Episode Summary: Dr. Rebecca Wynn speaks with Theresa “Terry” Grafenstine , a globally recognized leader in the audit profession and a respected voice in cybersecurity, risk, governance, and leadership. Terry has been named one of Security Magazine’s Top 10 Security Professionals (2021) and one of the Top Ten Audit Thought Leaders of the Decade by the Institute of Internal Auditors (IIA), which also inducted her into its Hall of Distinguished Practitioners . She has advanced the audit and accounting community through her service on the IIA’s North American and Global Boards of Directors , the AICPA Board of Directors , and as Global Chair of ISACA . Her career includes leadership roles at Citi and Deloitte, and she served as the Inspector General of the U.S. House of Representatives (2009–2017) . Terry also contributed to PenFed’s Supervisory Committee, serving as Chairwoman from 2014–2018. In this episode, Dr. Wynn and Terry share candid, humorous, and deeply practical leadership insights rooted in real-world experience. Episode highlights include: • How to build trust in a new organization • Communicating effectively with stakeholders • Setting boundaries as a leader Sponsor Produced in partnership with Click Solutions Group — providing cybersecurity leadership, strategy, and technology solutions for modern enterprises. Learn more: ClickSolutionsGroup.com 🎧 Listen Now Apple Podcasts: https://podcasts.apple.com/us/podcast/soulful-cxo/id1680649397 Spotify: https://open.spotify.com/show/4DJ67GCpreXLgy2VSa5Ire 🔗 Connect on LinkedIn / Social Dr. Rebecca Wynn: https://www.linkedin.com/in/RebeccaWynnCISSP Terry Grafenstine: https://www.linkedin.com/in/terry-grafenstine/ Support Buy Me a Coffee: https://www.buymeacoffee.com/soulfulcxo Resources / References (No additional resources provided for this episode) Hashtags #SoulfulCXO #Leadership #CyberSecurity #RiskManagement #AuditLeadership #Governance #ExecutiveInsight #WomenInLeadership #TrustBuilding #ProfessionalGrowth #ISACA #IIA #CISO #AICPA

April 16, 2024Episode 5526 min

Secrets to Building a Resilient Cybersecurity Program

Episode Summary: In this episode of Soulful CXO, Dr. Rebecca Wynn welcomes Rick Howard, Chief Security Officer for N2K, Chief Analyst and Senior Fellow at The CyberWire, and co-founder of the Cyber Threat Alliance. Rick brings decades of experience, including roles at Palo Alto Networks, TASC, iDefense, and the U.S. Army's Computer Emergency Response Team. They discuss: • Rick’s career journey and mentorship insights • Strategies for effective communication in cybersecurity leadership • CISO challenges and navigating risk and recovery • Why traditional security training is outdated • The “Chaos Monkey” architecture at Netflix and its lessons • Career advice for aspiring cybersecurity leaders This episode provides actionable strategies and expert perspectives for cybersecurity professionals, executives, and leaders navigating today’s rapidly evolving digital landscape. Sponsor Produced in partnership with Click Solutions Group — providing cybersecurity leadership, strategy, and technology solutions for modern enterprises. Learn more: ClickSolutionsGroup.com 🎧 Listen Now Apple Podcasts: https://apple.co/49vptby Spotify: https://open.spotify.com/show/4DJ67GCpreXLgy2VSa5Ire ✉️ Subscribe to the Soulful CXO Insights Newsletter https://lnkd.in/gY76RASc 📺 Follow the Soulful CXO YouTube Channel https://www.youtube.com/@soulfulcxo 🔗 Connect on LinkedIn / Social Dr. Rebecca Wynn: https://www.linkedin.com/in/RebeccaWynnCISSP Soulful CXO: https://www.linkedin.com/company/soulfulcxo Rick Howard: LinkedIn: https://www.linkedin.com/in/rickhoward/ Website: https://thecyberwire.com/ YouTube: https://www.youtube.com/channel/UCIC1L2vbbyotqEF0ZLhaOdw Resources / References • Cybersecurity First Principles: A Reboot of Strategy and Tactics : https://www.amazon.com/Cybersecurity-First-Principles-Strategy-Tactics/dp/1394173083 Support Buy Me a Coffee: https://www.buymeacoffee.com/soulfulcxo Hashtags #SoulfulCXO #Cybersecurity #CISO #Leadership #ExecutiveInsights #CyberRisk #Mentorship #CareerAdvice #CyberResilience #ITSecurity

March 19, 2024Episode 5330 min

Master Class: Learn Proactive Incident Response Techniques

Episode Summary: In this episode of Soulful CXO, Dr. Rebecca Wynn welcomes Sarah Armstrong-Smith , Microsoft’s Chief Security Advisor. Sarah brings deep experience across business resilience, crisis management, and cybersecurity, with leadership roles at Microsoft, the London Stock Exchange Group, Fujitsu, EY, and AXA. She has been on the front lines of major incidents, including IT failures, data breaches, and fraud. They discuss: • A holistic approach to business continuity and crisis management • Prioritizing people impact and critical decision-making during incidents • Lessons from real-world failures and high-pressure events • The shared responsibility model in cloud services • Why organizations must stay accountable for their data and user activity This Master Class episode provides essential insights for leaders strengthening their crisis readiness and security strategies. Sponsor Produced in partnership with Click Solutions Group — providing cybersecurity leadership, strategy, and technology solutions for modern enterprises. Learn more: ClickSolutionsGroup.com 🎧 Listen Now Apple Podcasts: https://apple.co/49vptby Spotify: https://open.spotify.com/show/4DJ67GCpreXLgy2VSa5Ire 📺 Follow the Soulful CXO YouTube Channel https://www.youtube.com/@soulfulcxo 🔗 Connect on LinkedIn / Social Dr. Rebecca Wynn: https://www.linkedin.com/in/RebeccaWynnCISSP Soulful CXO: https://www.linkedin.com/company/soulfulcxo Sarah Armstrong-Smith: https://www.linkedin.com/in/sarah-armstrong-smith Resources / References • Effective Crisis Management: https://www.amazon.com/Effective-Crisis-Management-Demonstrating-Experiences/dp/9355512716 • Understand the Cyber Attacker Mindset: https://www.amazon.com/Understand-Cyber-Attacker-Mindset-Counteract/dp/1398614289 Support Buy Me a Coffee: https://www.buymeacoffee.com/soulfulcxo Hashtags #SoulfulCXO #CyberResilience #CrisisManagement #BusinessContinuity #Leadership #CloudSecurity #IncidentResponse #SecurityStrategy #TechLeadership #Cybersecurity

January 7, 2025Episode 7312 min

Elevate Your Leadership: Unlock Your True Potential

Episode Summary: In this episode of Soulful CXO , Dr. Rebecca Wynn welcomes executive coach Debra Benton to discuss the critical role of executive presence in leadership. They explore: How to be memorable, credible, and trusted as a leader Developing authenticity and confidence without arrogance Aligning words and actions to inspire and motivate teams Fostering consideration, self-esteem, and adaptability in leadership styles Overcoming imposter syndrome while enhancing leadership effectiveness Debra shares practical strategies to help leaders elevate their influence and foster a positive organizational culture. Sponsor Produced in partnership with Click Solutions Group — providing cybersecurity leadership, strategy, and technology solutions for modern enterprises. Learn more: ClickSolutionsGroup.com 🎧 Listen Now Apple Podcasts: https://apple.co/49vptby Spotify: https://open.spotify.com/show/4DJ67GCpreXLgy2VSa5Ire ✉️ Subscribe to the Soulful CXO Insights Newsletter https://lnkd.in/gY76RASc 📺 Follow the Soulful CXO YouTube Channel https://www.youtube.com/@soulfulcxo 🔗 Connect on LinkedIn / Social Dr. Rebecca Wynn: https://www.linkedin.com/in/RebeccaWynnCISSP Soulful CXO: https://www.linkedin.com/company/soulfulcxo Debra Benton: LinkedIn | Twitter | Facebook Resources / References Executive Presence for the Modern Leader An Introvert's Guide to Networking Secrets of A CEO Coach How to Think Like a CEO Support Buy Me a Coffee Hashtags #SoulfulCXO #Leadership #ExecutivePresence #CISO #Cybersecurity #Business #CareerGrowth #ProfessionalDevelopment #LeadershipCoaching #ExecutiveCoaching

September 2, 2025Episode 8115 min

Leadership Struggle: Habits that Protect Your Energy

Episode Summary: In this episode of Soulful CXO , Dr. Rebecca Wynn speaks with Jason Elrod, Chief Information Security Officer for MultiCare Health System, a healthcare organization in the Pacific Northwest. They discuss: How early programming experience and a people-first mindset helped Jason rise to leadership without a traditional college degree Balancing ambition with energy and habits for long-term success The importance of clear communication, setting boundaries, and taking time off to avoid burnout Challenges with common hiring practices in cybersecurity and advice for those breaking into the field This episode is a reminder that protecting your energy is essential to effective leadership. Sponsor Produced in partnership with Click Solutions Group — providing cybersecurity leadership, strategy, and technology solutions for modern enterprises. Learn more: ClickSolutionsGroup.com 🎧 Listen Now Apple Podcasts: https://apple.co/49vptby Spotify: https://open.spotify.com/show/4DJ67GCpreXLgy2VSa5Ire ✉️ Subscribe to the Soulful CXO Insights Newsletter https://lnkd.in/gY76RASc 📺 Follow the Soulful CXO YouTube Channel https://www.youtube.com/@soulfulcxo 🔗 Connect on LinkedIn Dr. Rebecca Wynn: https://www.linkedin.com/in/RebeccaWynnCISSP Soulful CXO: https://www.linkedin.com/company/soulfulcxo Jason Elrod: https://www.linkedin.com/in/thejasonelrod/ Resources / References Adapting Without Compromising Integrity: A Leadership Lesson in Security & Politics Sustaining a Feedback Culture: Advanced Techniques and Real-Life Examples How to Be Successful in Navigating a New Organization Support Buy Me a Coffee Hashtags #SoulfulCXO #Leadership #ExecutiveLeadership #Cybersecurity #CISO #Technology #Business #CareerGrowth #SecurityStrategy #Resiliency

November 12, 2024Episode 7015 min

AI in Cybersecurity: Hero or Villain

Episode Summary: In this episode of Soulful CXO, Dr. Rebecca Wynn sits down with Chuck Brooks, President of Brooks Consulting. They discuss: • The double-edged role of artificial intelligence in cybersecurity — automating threat detection while posing potential risks • Strategies to address the cybersecurity talent gap using AI • Proactive risk management and robust cyber hygiene for businesses of all sizes • Supply chain risks and the importance of securing interconnected systems • Unique challenges SMBs face in navigating an evolving security landscape This episode provides actionable insights for executives and cybersecurity leaders looking to leverage AI safely and strengthen their organization’s security posture. Sponsor Produced in partnership with Click Solutions Group — providing cybersecurity leadership, strategy, and technology solutions for modern enterprises. Learn more: ClickSolutionsGroup.com 🎧 Listen Now Apple Podcasts: https://apple.co/49vptby Spotify: https://open.spotify.com/show/4DJ67GCpreXLgy2VSa5Ire ✉️ Subscribe to the Soulful CXO Insights Newsletter https://lnkd.in/gY76RASc 📺 Follow the Soulful CXO YouTube Channel https://www.youtube.com/@soulfulcxo 🔗 Connect on LinkedIn / Social Dr. Rebecca Wynn: https://www.linkedin.com/in/RebeccaWynnCISSP Soulful CXO: https://www.linkedin.com/company/soulfulcxo Chuck Brooks: LinkedIn: https://www.linkedin.com/in/chuckbrooks Twitter: https://twitter.com/chuckdbrooks Resources / References • Inside Cyber: How AI, 5G, IoT, and Quantum Computing Will Transform Privacy and Our Security — https://a.co/d/j7Y0BGB • Dr. Rebecca Wynn, Navigating the Future: Strategic Vision for 5G Network Security with AI and ML — https://www.linkedin.com/pulse/navigating-future-strategic-vision-5g-network-al-ml-dr-rebecca-tr0tc/ Support Buy Me a Coffee: https://www.buymeacoffee.com/soulfulcxo Hashtags #SoulfulCXO #Leadership #ExecutiveLeadership #Cybersecurity #AI #Technology #Business #CareerGrowth #SecurityStrategy #Resiliency

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