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Someone Else's Debt

A Quantitative Framework for Cyber Diligence at Deal Speed

Cyber risk in M&A gets treated as a compliance check, a heat-map of red and yellow boxes, or a problem to deal with after close. By then it is too late.

Quantitative Cyber Diligence (QCD) replaces qualitative cyber diligence with a five-pillar framework that produces a single dollar-denominated figure the investment committee can argue about — calibrated, defensible, and reproducible. Each pillar maps to a measurable exposure: external attack surface, vendor concentration, data sensitivity, security program maturity, and integration risk. The framework aggregates per-pillar exposures with explicit correlation discount, surfaces tail-driver scenarios that conventional analysis misses, and translates the aggregate figure into deal-architecture recommendations: reps and warranties, escrow, price adjustment, or walk-away.

This book documents how QCD engagements actually run. Two worked examples (healthcare-IT and industrial-IT). Practitioner templates. Per-pillar pseudocode. Industry loss benchmarks. The complete framework, calibrated to the post-Change-Healthcare era.

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About

About

About the Book

A deal closes. Eighteen months later, the breach hits. Cyber risk that wasn't priced into the deal architecture becomes a cost the acquirer absorbs alone — sometimes in the billions.

Quantitative Cyber Diligence is the framework that prevents this. Five pillars. Correlation-adjusted aggregation. A single dollar figure the investment committee can argue about. Calibrated, defensible, and reproducible across the deal-process lifecycle.

This is the practitioner's guide to running QCD engagements at deal speed — Tier 1 snapshots in seventy-two hours, Tier 2 full diligence in five days, continuous post-close monitoring across the multi-year hold period. Two worked examples, twelve operational chapters, five appendices, and the engagement-evidence learning loop that compounds calibration improvement across the engagement corpus.

Author

About the Author

Yolonda Smith

Yolonda Smith is a cybersecurity executive, startup founder, and U.S. Air Force veteran with over 20 years in the field. She has served as Head of Cybersecurity at Grubhub and sweetgreen — where she led security through the company's IPO — and as Business Information Security Officer at Target. She held product leadership roles at Pwnie Express and spent eight years as an Air Force Cyberspace Operations Officer. Yolonda is the founder and CEO of vCISO Lite, which delivers automated compliance and risk management for small and mid-size businesses. She holds a Certified CISO credential from Carnegie Mellon's Heinz College and maintains CISSP, CISM, GSEC, and GCIH certifications. She lives in Atlanta.

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