Brent Gifford
30-year CIO/CISO. Two newsletters: the Digital Safety Playbook — plain-English online safety for everyday people (scams, fake stores, protecting your accounts and family) — and the CIO & CISO Executive Brief, governance for security leaders.
| Platform |  | Pricing | Only free issues | Publishes | Daily |
|---|---|---|---|---|---|
| Issues | 77 | Founded | 8 months ago | Last Issue | 4 days ago |
| Active | |||||
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brentdgifford.substack.comLatest Issues
CIO Executive Brief #36 — Adjudication Is the Constraint
TL;DR
· Every AI deployment in the technology function increases the volume of things requiring a human decision while leaving unchanged the number of humans who can make those decisions. The work AI removes and the work it creates are dif...
CISO Executive Brief #36 — The Trust Chains You Cannot Migrate in a Hurry
TL;DR
· The post-quantum date moved and most programs have not noticed. Google set 2029 in March — a year ahead of NIST’s 2030 deprecation and six ahead of the 2035 disallowance — and Microsoft and Cloudflare followed. Two executive orders...
CIO Executive Brief #35 — Government-Gated Frontier AI
TL;DR
· Executive Order 14409, signed 2 June 2026, established a classified benchmarking process to designate “covered frontier models” and a framework under which developers give the US government thirty days of pre-release access before...
CISO Executive Brief #35 — When AI Exposes Inconsistent Security Judgment
TL;DR
· Judgment-capture systems are sold as scale: encode how your best analyst triages, then apply it everywhere. The pitch is consistency. The first thing you actually get is a measurement — and it is usually of variance nobody knew was...
CIO Executive Brief #34 — The Semantic Layer Is Where Your AI Strategy Succeeds or Fails
TL;DR
· Most organizations diagnose the pilot-to-production gap as a model problem and buy their way toward a data problem. The constraint is rarely capability. It is that the same metric is calculated three different ways in finance, mark...
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30-year CIO/CISO. Two newsletters: the Digital Safety Playbook — plain-English online safety for everyday people (scams, fake stores, protecting your accounts and family) — and the CIO & CISO Executive Brief, governance for security leaders.
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