In this episode of Ctrl-Alt-Secure, Valentina Flores sits down with Timothy Shields, Partner at Kelley Kronenberg, to unpack what data privacy law really looks like when it meets real-world technology, security, and business constraints.

Timothy brings a rare perspective to privacy law, having started his career as a software developer and academic before becoming a tech and data privacy attorney. That technical background shapes how he advises companies today—moving away from unrealistic “zero-risk” thinking and toward practical, defensible decision-making.

The conversation explores where organizations most often misunderstand data privacy requirements, why documentation and intent matter as much as tools, and how companies can reduce legal exposure before something goes wrong. Valentina and Timothy also discuss breach response, AI-related legal risk, and why small companies are just as exposed as large enterprises.

Key topics covered in this data privacy episode:

• Why legal risk in tech is rarely “zero risk” — and why that mindset fails
• How a technical background changes the way privacy law is applied in practice
• Common privacy blind spots engineers and executives overlook
• The biggest legal mistakes companies make after a breach
• Why proactive security testing and planning matter more than perfection
• The critical role of documentation when regulators or courts get involved
• Why not doing what you said you would do creates more liability than getting breached
• Where AI liability is headed and what companies should be doing now
• Why “we’re too small to be a target” is one of the most dangerous privacy myths

Who should listen?

This episode is essential for founders, executives, legal teams, engineers, security leaders, and anyone responsible for handling customer data, building software, or managing cyber risk. If your company collects, processes, or stores data—or is experimenting with AI—this conversation offers practical guidance you can actually act on.

About Ctrl-Alt-Secure

Ctrl-Alt-Secure is brought to you by Red Sentry, a human-led, tech-powered penetration testing firm helping companies identify and fix vulnerabilities before attackers can exploit them.

🔗 Learn more about Kelly Kronenberg: https://www.kelleykronenberg.com/
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