Join hosts Fern and Troy as they sit down with legendary negotiator and cybersecurity expert Jean Shapiro (formerly of American Express) for an in-depth discussion on navigating cybersecurity budgets, building trust with vendors, leveraging crises for improvement, and fostering a culture of transparency. From managing $2B budgets to avoiding sales pitfalls and tying security to business impact, Jean shares real-world insights from her decades in the field. Whether you’re dealing with ransomware recovery, brand protection, or innovation funding, this episode is packed with gold nuggets for CISOs, security leaders, and vendors alike.

If you enjoy raw, unfiltered conversations on cyber defense, hit that LIKE button, SUBSCRIBE for more episodes, and drop a comment below: What’s your biggest budgeting challenge in cybersecurity?

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#Cybersecurity #CISOBudget #SecurityFunding #VendorManagement #Ransomware #CISOAdvice

Timestamps:

00:00 – Intro & Jean Shapiro’s Epic Entrance

03:27 – Why Non-Tech Leaders Struggle to Understand Security

06:10 – Educating Buyers Through Breach News & Real-World Examples

09:06 – Gold Nugget #1: Never Let a Good Crisis Go to Waste

12:36 – Building a Culture of Transparency (No Finger-Pointing)

16:21 – Partnering with CIOs: Fixing Legacy Issues Without Blame

18:46 – Getting Budget: Tie Security to Revenue Loss & Business Impact

23:29 – Risk & Brand Protection in Budget Conversations

26:11 – Risks Breakdown: Litigation, Regulation, Operational Downtime

28:00 – Ransomware Myths: Why Paying Isn’t a Quick Fix

31:56 – Frameworks (NIST, MITRE ATT&CK) for Data-Driven Budgets

37:32 – Carving Out Budget for Innovation & AI Tools

40:46 – Tips: Align with Strategic Initiatives (Don’t Just Slap AI on It)

43:02 – Sales Call Frustrations: “What Keeps You Up at Night?”

47:19 – Protecting Proprietary Info in Vendor Calls (No Recordings!)

51:23 – Post-Sale Support: Don’t Ghost After the Deal

55:38 – Burning Vendor Bridges: When to Replace Tools

58:03 – Sales Ghosting Between Roles: It Bites Back

1:05:16 – Sales Incentives Exposed: Why Renewals Get Weird

1:10:20 – Negotiating with VARs: Avoid Desperation Deals

1:19:00 – Closing Thoughts: Know Your Numbers, Talk Business Language

Thanks for watching! Stay secure out there.

Linkedin:

Damian: https://www.linkedin.com/in/damianchung/

Troy: https://www.linkedin.com/in/kosovotroy/

Fern: https://www.linkedin.com/in/fernrojasaz/