How do you strengthen your cybersecurity posture before attackers find the gaps?

In Part Two of this proactive cybersecurity series, Christian Redshaw and Zach(ary) Eikenberry are joined once again by Laura Payne, CEO of White Tuque and Robert D Stewart, Founder, Chairman, and Head of Strategic Threat Intelligence at White Tuque.

This episode explores the proactive practices that help organizations reduce cyber risk before an attack happens. From penetration testing and vulnerability management to security awareness training, Laura and Rob explain how security leaders can prioritize the right risks, empower their people, and build stronger, more resilient organizations.

In this episode, you'll learn about:

1. The biggest myths surrounding penetration testing

2. Why security testing improves more than just security

3. Prioritizing vulnerabilities based on real business risk

4. Common mistakes organizations make with vulnerability management

5. Building a security-aware culture without blame

6. Why continuous awareness training delivers better results

Whether you're an MSP, IT leader, cybersecurity professional, or business executive, this episode provides practical guidance on proactive cybersecurity, penetration testing, vulnerability management, security awareness, and cyber resilience.

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How prepared is your organization for a cyber incident?

In this episode of the Digital Trust Podcast, Christian Redshaw and Zach(ary) Eikenberry are joined by Laura Payne, CEO of White Tuque, and Rob Stewart, Founder, Chairman, and Head of Strategic Threat Intelligence at White Tuque, for Part One of a two-part series on proactive cybersecurity and cyber incident response.

Together, they discuss why effective incident response starts long before a ransomware attack or security breach occurs. From defining decision-makers and communication plans to testing response procedures through tabletop exercises, they share practical strategies that help organizations strengthen cyber resilience and respond with confidence when an incident happens.

In this episode, you'll learn about:

• Preparing for the response—not just the attack
• The building blocks of an effective incident response plan
• Identifying decision-makers before a crisis
• Why incident response is a business-wide responsibility
• Keeping your response plan current and tested
• Key lessons from real-world incident response

Whether you're an MSP, IT leader, cybersecurity professional, business executive, or part of an incident response team, this episode offers practical advice to help you improve cyber preparedness, strengthen business continuity, and build a more resilient security program.

Subscribe to the Digital Trust Podcast for more conversations on cybersecurity, digital trust, risk management, security leadership, and practical strategies for building resilient organizations.

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Calling employees a "human risk" is costing your security program before training even starts.

David Shipley, CEO of Beauceron Security, makes the case for reframing the whole category on the Digital Trust podcast.

• "Human Risk Management" signals to employees they're liabilities, not assets — it's demotivating by design
• The goal is helping people make good choices with technology, not minimising the human
• New employees are higher risk than any specific role; target behaviour, not job title
• Security Awareness data shows over-training suppresses reporting rates
• The answer is frequency, not volume

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Shame-based security training only hides incidents. So, what's the real solution here?

David Shipley, CEO of Beauceron Security, makes that case on the Digital Trust Podcast and explains what actually builds a security culture that works.

• Why walls of shame silence the reporting you need most.

• Why "we care, you matter" is the most important security message leadership can send.

• How knowledge and vigilance are both required, and why most programs only develop one.

If your security strategy focuses more on controlling people than empowering them, this episode is a must-watch.

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Zero trust gives you the ability to know what and who to trust.

On Season 2 Episode 18 of the Digital Trust Podcast, host Christian Redshaw and co-host Zach(ary) Eikenberry sit down with Scott Peterson, CSO of Cyber Solutions, CTDO at Lyra Recovery, and CSO of a managed zero trust environment, to unpack why organizations struggle with proactive security and what it really takes to build a mature zero trust strategy.

Drawing from years of experience in cybersecurity leadership, incident recovery, and managed services, Peterson shares practical lessons from real-world recovery cases, including the overlooked gaps that continue to leave organizations exposed.

The conversation dives into:

• Why Zero Trust starts with mindset, not tools

• The most common security gaps organizations still ignore

• Why reactive security creates long-term risk

• Practical first steps toward a mature security posture

• The importance of executive buy-in for cybersecurity success

If your security strategy only starts after something breaks… this episode is a must-watch.

#DigitalTrustPodcast #CyberSecurity #ZeroTrust #MSP

#RiskManagement #ITLeadership #DigitalTrust

#CyberResilience #ScottPeterson #ChristianRedshaw

#ZackEikenberry #PeopleProcessTechnology

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We want to have all the answers. But have you ever thought if it would be better to ask the right questions, instead?

On Season 2 Episode 17 of the Digital Trust Podcast, host Christian Redshaw and co-host Zach(ary) Eikenberry sit down with Scott Peterson, CSO of Cyber Solutions, CTDO at Lyra Recovery, and CSO of Managed Zero Trust, to unpack what truly separates effective security leaders and mature MSPs from the rest.

With experience spanning multiple leadership roles across security, recovery, and managed services, Peterson shares why listening—not tooling—is the most underrated skill in cybersecurity, and how over-reliance on reactive solutions is holding organizations back.

The conversation dives into:

• Why listening skills are a security leader’s biggest advantage

• The hidden impact of imposter syndrome in cybersecurity teams

• Reactive vs. proactive security and why most MSPs get stuck

• What an unhealthy vs. mature MSP actually looks like

• Why security needs a seat at the executive table

If your security strategy starts after something breaks… this episode will challenge how you think.

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AI is making phishing smarter… are we becoming weaker?

On Season 2 Episode 16 of the Digital Trust podcast, host Christian Redshaw and co-host Zach(ary) Eikenberry sit down once again with Gavin Roberts, CTO of Topsec Cloud Solutions, to continue the conversation on the evolving realities of email security.

Drawing from decades of experience in fraud detection and cybersecurity, Roberts offers a grounded perspective on the industry’s growing reliance on AI, emphasizing the importance of maintaining strong technical foundations alongside emerging tools.

The discussion highlights how email continues to dominate as the primary attack vector, why improved phishing quality hasn’t necessarily translated to better detection outcomes, and how overdependence on automation can introduce new risks within security teams. Roberts also reinforces the need for layered security approaches, ensuring organizations aren’t relying solely on default protections.

If your organization is leaning heavily on AI without reinforcing fundamentals, this is a conversation worth tuning into.

#DigitalTrustPodcast #CyberSecurity #EmailSecurity #AI

#Phishing #ITLeadership #RiskManagement #DigitalTrust

#GavinRoberts #ChristianRedshaw #ZackEikenberry #PeopleProcessTechnology

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90% of cyberattacks still start with email yet most organizations are still underestimating it.

On Season 2 Episode 15 of the Digital Trust podcast, host Christian Redshaw and co-host Zach(ary) Eikenberry sit down with Gavin Roberts, CTO of Topsec Cloud Solutions, to unpack why email security remains one of the biggest and most misunderstood risks in cybersecurity.

With over 25 years of experience across fraud detection, financial systems, and email security, Roberts shares why AI is making phishing attacks more convincing than ever, while also warning against over-reliance on automation without maintaining strong technical fundamentals.

The conversation dives into:

• Why email continues to be the #1 attack vector

• The real impact of AI on both attackers and defenders

• Why layered security beats “all-in-one” solutions

• The growing risk of skill gaps in security teams

If you're relying on default email security alone… this episode is a must-watch.

#DigitalTrustPodcast #CyberSecurity #EmailSecurity #AI

#Phishing #ITLeadership #RiskManagement #DigitalTrust

#GavinRoberts #ChristianRedshaw #ZackEikenberry #PeopleProcessTechnology

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On Season 2 Episode 14 of the Digital Trust podcast, host Christian Redshaw and co-host Zach(ary) Eikenberry welcome back Grady J. Global Director of Business Development at eSentire.

Building on his experience across CIO, CSO, and product leadership roles, Johnston shares practical insights on how IT leaders can rethink vendor relationships; not as transactional exchanges, but as strategic partnerships that advise, support, and enable business growth.

The conversation dives into how to evaluate vendors beyond price, why proof-of-concept testing in controlled environments is critical in today’s fast-moving AI landscape, and how organizations can leverage vendor ecosystems to reduce costs while strengthening internal capabilities. Johnston also highlights the importance of aligning technology decisions with broader business outcomes, helping IT teams move from reactive cost centers to proactive strategic drivers.

#DigitalTrustPodcast #CyberSecurity #ITLeadership #VendorManagement #StrategicPartnerships #RiskManagement #ITStrategy #DigitalTrust #GradyJohnston #ChristianRedshaw #ZackEikenberry #PeopleProcessTechnology

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On Season 2 Episode 13 of the Digital Trust podcast, host Christian Redshaw and co-host Zach(ary) Eikenberry sit down with Grady J. Johnston, Global Director of Business Development for eSentire.

Drawing from experience as a CIO, CSO, IT director, and product leader, Johnston shares practical insights on building effective security teams and strengthening the relationship between IT and the broader business.

The conversation explores why mentorship and continuous training are essential for growing IT talent, how IT leaders can leverage vendor ecosystems for free training and development resources, and why cultivating long-term professional networks creates lasting value across organizations. Johnston also explains how forming cross-department compliance committees can help IT leaders gain strategic buy-in for security initiatives and technology changes—transforming IT from a cost center into a strategic business partner.

#DigitalTrustPodcast #CyberSecurity #ITLeadership #Mentorship #ChangeManagement #VendorPartnerships #ITStrategy #DigitalTrust #GradyJohnston #ChristianRedshaw #ZackEikenberry #PeopleProcessTechnology

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