Soulful CXO

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

Hashtags

#SoulfulCXO #MargaretHamilton #SoftwareEngineering #Apollo11 #CyberSecurity #Leadership #ExecutiveInsight #RiskManagement #SystemsDesign #CISO

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

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Hashtags

#SoulfulCXO #Leadership #ExecutiveLeadership #Integrity #Audit #Cybersecurity #RiskManagement #CISO #Privacy #PrivacyByDesign #BusinessEthics #ISO31700 #GDPR

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

Episode Summary:
In this episode of Soulful CXO, Dr. Rebecca Wynn sits down with Jack Leidecker, Chief Information Security Officer at Gong, a leading revenue intelligence platform. They discuss:

• Challenges CISOs face in communicating cybersecurity needs to business leaders
• How to select projects that deliver real business value
• Writing effective business cases and navigating misaligned security strategies
• Identifying red flags when vetting leadership roles

This episode provides actionable insights for cybersecurity leaders looking to align career moves with long-term success and business 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
Jack Leidecker: https://www.linkedin.com/in/jackleidecker/

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

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

Episode Summary:
In this episode of Soulful CXO, Dr. Rebecca Wynn speaks with Avani Desai, CEO and President of Schellman & Company, a leading CPA firm specializing in technology and security assessments. They discuss:

• Avani’s journey from growing up as the daughter of Indian immigrants to leading a top 100 accounting firm
• Building a successful career without compromising identity, values, or personal life
• The importance of mentorship, prioritization, and staying aligned with purpose
• Leading in male-dominated industries while remaining authentic and creating space for others

This episode is a powerful reminder that leadership begins with self-awareness and a clear sense of what truly matters.

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
Avani Desai: https://www.linkedin.com/in/avanidesai/
Avani on Twitter: https://twitter.com/avanidesai

Resources / References

• Roadmap for Assessing and Selecting Generative AI
• Schellman Blog
• MyCryptoAlert App

Support

Buy Me a Coffee

Hashtags

#SoulfulCXO #Leadership #ExecutiveLeadership #Cybersecurity #CISO #Technology #Business #CareerGrowth #SecurityStrategy #Resiliency

Episode Summary:
In this episode of Soulful CXO, Dr. Rebecca Wynn welcomes Jane Frankland, a leader in cybersecurity known for her expertise in leadership and promoting diversity of background and experience. They discuss:

• The persistent challenges CISOs face in securing a seat at the leadership table
• How effective communication and trust-building create lasting partnerships
• Industry burnout and aligning leadership values with actions
• The importance of fostering diverse perspectives to navigate complex cybersecurity challenges

This episode provides practical insights for leaders aiming to improve organizational impact while supporting inclusive, resilient teams.

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
Jane Frankland:

• LinkedIn

Resources / References

• Roadmap for Assessing and Selecting Generative AI
• Gartner Predicts Nearly Half of Cybersecurity Leaders Will Change Jobs by 2025
• ISC2 Research Finds Some Progress, But More Needs to be Done to Support Women in Cybersecurity

Support

Buy Me a Coffee

Hashtags

#SoulfulCXO #Leadership #ExecutiveLeadership #Cybersecurity #CISO #Technology #Business #CareerGrowth #SecurityStrategy #Resiliency #DiversityInTech #WomenInCybersecurity

Episode Summary:
In this episode of Soulful CXO, Dr. Rebecca Wynn welcomes Chris Roberts - also known as “Dr. Dark Web” - AI & Deepfake Cyber Strategist at World Wide Technology and a renowned expert in counter-threat intelligence. They discuss:

• The hidden risks of generative AI and AI-generated misinformation
• Data manipulation and adversarial intelligence eroding trust in digital content
• Critical thinking, multi-source verification, and ongoing education as defenses against disinformation
• How organizations can move beyond checkbox training to build a culture of awareness, responsibility, and vigilance

This episode offers actionable strategies for leaders to navigate the evolving AI and cybersecurity 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
Chris Roberts: LinkedIn
Chris Roberts Bio / Website: WWT Profile

Resources / References

• Roadmap for Assessing and Selecting Generative AI
• Deepfakes for Good? How AI is Powering the Next Era of Personalization
• Deepfake Deception: Can You Trust What You See and Hear?

Support

Buy Me a Coffee

Hashtags

#SoulfulCXO #Leadership #ExecutiveLeadership #Cybersecurity #AI #Deepfakes #Technology #Business #CareerGrowth #SecurityStrategy #Resiliency #DigitalTrust #CyberAwareness

Episode Summary:
In this episode of Soulful CXO, Dr. Rebecca Wynn welcomes Joey Johnson, CISO at Premise Health, who brings a unique background in archaeology and hospitality to cybersecurity leadership. They discuss:

• Aligning security with organizational strategy through strong internal relationships and understanding business risk tolerance
• Using storytelling, not just metrics, to resonate with boards
• Listening as one of the most powerful leadership tools
• A human-centered approach to managing risk and enabling innovation in rapidly evolving healthcare and tech environments

This episode offers actionable insights for leaders seeking to balance technical expertise with emotional intelligence and strategic 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 / Social

Dr. Rebecca Wynn: https://www.linkedin.com/in/RebeccaWynnCISSP
Soulful CXO: https://www.linkedin.com/company/soulfulcxo
Joey Johnson: LinkedIn

Resources / References

• Diverse Experiences: The Key to Stronger Security Leadership
• Lead with Authenticity: Embrace Your True Self
• Sustaining a Feedback Culture: Advanced Techniques and Real-Life Examples

Support

Buy Me a Coffee

Hashtags

#SoulfulCXO #Leadership #ExecutiveLeadership #Cybersecurity #CISO #Technology #Business #CareerGrowth #SecurityStrategy #Resiliency #HumanCenteredLeadership

Episode Summary:
In this episode of Soulful CXO, Dr. Rebecca Wynn welcomes Randi Levin, a pioneering technology executive with leadership experience at NASA JPL, the City of Los Angeles, NBC Universal, and more. They discuss:

• How Randi’s early career transitions shaped her leadership style
• The importance of strategic communication and explaining the “why” behind decisions
• Navigating challenges as women in male-dominated industries
• Using empathy to foster trust, alignment, collaboration, and innovation
• Overcoming barriers while implementing forward-thinking IT strategies

This episode provides actionable insights for leaders aiming to build resilient, innovative, and inclusive organizations.

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
Randi Levin: LinkedIn
Websites: RandiLevin.net | TheRelevanceArchitect.com

Resources / References

• Women in Tech Accelerator

Support

Buy Me a Coffee

Hashtags

#SoulfulCXO #Leadership #ExecutiveLeadership #Technology #WomenInTech #Cybersecurity #Business #CareerGrowth #Resiliency #StrategicCommunication #Innovation