Beyond Checkbox Compliance

In this special International Women's Day episode, host Suzie Smibert, COO of RESTIV Technology, brings together an incredible panel of women in cybersecurity and tech leadership. They discuss the challenges of breaking into and thriving in a male-dominated industry, the importance of sponsorship over mentorship, and how to foster a more inclusive and diverse cybersecurity workforce.

Featuring:

• Megan Anderson, Chief of Staff at RESTIV Technology
• Jessica Wiseman, Director, Strategy and Transformation Office, PwC Canada
• Amy Caughlin, Co-Founder & Chief Growth Officer, Jazzberry
• Selina Lamb, Service Delivery Manager, Product Management, Fortinet

From imposter syndrome to the power of sponsorship, from career pivots to claiming space in the room, this conversation is an unfiltered look at what it takes to succeed in cybersecurity and beyond. If you're a woman in tech, aspiring to lead, or looking for actionable insights on supporting diversity in your organization, this is a must-listen episode.

Topics Covered:

• Biggest career challenges and how to overcome them
• Why cybersecurity is still underrepresented by women
• The impact of sponsorship vs. mentorship
• How flexible work policies (done right) can increase retention
• The importance of visibility and role models in cybersecurity
• Rewriting outdated hiring processes to attract diverse talent
• Advice for women looking to break into cybersecurity or advance in leadership

Notable Quotes:

💡 "We all have imposter syndrome. We all think it's unique to ourselves, but it's not. Nobody really knows what they're doing when they start out—just dig deep." – Amy Caughlin

💡 "Say it anyway. Just do it anyway. Find your voice, claim your space." – Megan Anderson

💡 "You may help others grow by doing the hard thing. So find that motivation somewhere else." – Selina Lamb

💡 "Find a team where people light up when you enter the room. That's where you want to be." – Jessica Wiseman

💡 "Sponsorship isn't just about opening doors—it's about putting someone's name in the room when they aren't there to speak for themselves." – Suzie Smibert

Key Takeaways for Listeners:

✔️ Own Your Space – Confidence is key, and so is surrounding yourself with people who believe in you.

✔️ Sponsorship Over Mentorship – Advocates who champion your career make the biggest difference.

✔️ Diverse Hiring Needs a Reboot – The traditional "tech bro" pipeline is outdated—skills and leadership matter more than rigid job descriptions.

✔️ Flexible Work Isn't Just About Fridays Off – True flexibility acknowledges different needs, from working parents to non-traditional work styles.

✔️ Network Relentlessly – Sometimes, your sponsor won't come from your company—build and nurture a strong external network.

✔️ Step Into Challenges – Leadership isn't about knowing everything, it's about being willing to take the lead.

Resources & Ways to Connect:

🌐 Learn More About RESTIV Technology: https://restiv.io

📩 Connect with the Guests on LinkedIn:

• Suzie Smibert

• Megan Anderson

• Jessica Wiseman

• Amy Caughlin

• Selina Lamb

🔗 Join the Conversation!

Tag us on LinkedIn and share your biggest takeaways from this episode using #WomenInCyber #Leadership #DiversityInTech

Security frameworks, regulatory acronyms, and "best practices" can only get you so far—especially when they're not built for how people actually work. In this episode, Devon is joined by Tim McCreight, Founder and CEO of Tale Craft Security, for a no-BS conversation on what businesses are getting wrong when it comes to security, and how a risk-based approach (the kind that actually works) is built on understanding people first.

Tim shares his journey from security executive to entrepreneur, what led him to build Tale Craft Security, and why storytelling—not scare tactics—is the key to building security programs that stick. From boardrooms to frontlines, this episode breaks down what it takes to move past fear and build resilience.

What You'll Learn in This Episode:

• Why focusing on human behavior is more important than any technical control.

• The real definition of risk (spoiler: it's not just about threats).

• How to align security programs with business goals—without the jargon.

• Why boards and executives need to rethink their role in cybersecurity.

• How better storytelling can bridge the gap between security teams and decision-makers.

Key Themes:

• Risk as Business Impact: Security decisions are business decisions—treat them that way.

• Human-Centered Security: People will work around your tools if they don't buy in.

• Storytelling Over Fear: Security leaders need to explain risk like it's a story—not a legal briefing.

• The Power of Sharing: Cyber adversaries collaborate—why don't we?

Memorable Quotes:

• "The effect of uncertainty on objectives—that's risk." – Tim McCreight

• "You don't need to be afraid of the chainsaw, but you'd better respect it." – Devon Smibert

• "Security professionals need to get better at telling stories—because that's how businesses actually understand risk." – Tim McCreight

Guest Spotlight:

Tim McCreight is the Founder and CEO of Tale Craft Security, a consultancy built on helping businesses understand risk, make better decisions, and build security programs that enable growth. Tim is a 45-year industry veteran, former President of ASIS International, and host of the long-running podcast Caffeinated Risk.

Resources Mentioned:

• Tale Craft Security – talecraftsecurity.com

• RESTIV: Cybersecurity Without Surprises – restiv.io

• Caffeinated Risk Podcast – Caffeinated Risk

• ISO 31000 Definition of Risk: "The effect of uncertainty on objectives"

Join the Movement:

RESTIV is rewriting the cybersecurity playbook—no fear, no fluff, just clarity.

👉 Follow RESTIV on LinkedIn for unfiltered insights: RESTIV LinkedIn

👉 Learn more at restiv.io

#CybersecurityWithoutSurprises #RESTIV #TaleCraftSecurity #BusinessRisk #SecurityThatWorks #ResilientBusiness #CyberRiskManagement #StorytellingSecurity

Hosted by Devon Smibert

"Security is everybody's responsibility. It's not just for the IT department."

In this episode of the 'Beyond Checkbox Compliance' podcast, host Devon Smibert sits down with Terry Singleton, a seasoned cybersecurity expert and sales leader.

Terry shares his unconventional journey from writing HTML in the dot-com bubble era to leading innovation at companies like Palo Alto Networks and Daz. Learn how his technical background has shaped his sales approach and discover valuable lessons about operationalizing technology, balancing security with business innovation, and the evolving cybersecurity landscape.

Whether you're an aspiring cyber defender or an industry veteran, this episode is packed with actionable insights.

Key Highlights:

• How Terry's high school math teacher inspired his interest in technology.
• The transition from coding to cybersecurity and sales leadership.
• Why operationalizing technology is just as important as innovation.
• Stories from the early days of cybersecurity at Palo Alto Networks.
• The importance of automation and unifying data in modern cybersecurity.
• Advice for aspiring cybersecurity professionals and organizations seeking innovation.

Security doesn't have to be a barrier

If today's conversation sparked your curiosity or gave you a fresh perspective on cybersecurity and innovation, we'd love to hear from you!

At RESTIV, we're all about helping businesses navigate the ever-changing security landscape with confidence. Whether you're looking to solve challenges, explore new opportunities, or simply connect with experts who care, we're here for you.

Visit us at https://restiv.io to learn more, get in touch, or join the conversation.