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 | 69 | Founded | 8 months ago | Last Issue | 4 days ago |
| Active | |||||
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brentdgifford.substack.comLatest Issues
CIO Executive Brief #33 — The Pipelines Nobody Owns: An Operating Model for Automation and Integration Workloads
TL;DR
· Automation stopped being a back-office scheduling tool and became the operational layer coordinating infrastructure, applications, data pipelines, and AI workflows across the enterprise. The 2026 state-of-automation benchmark puts...
CISO Executive Brief #33 — Your AI Platform Is the Newest Vendor on Your Risk Register, and the Largest
TL;DR
· On August 9 at DEF CON, Tenet Security demonstrated Ghostjacking — an attack that plants instructions inside a security log, waits for an analyst to ask an AI agent to review the event, and lets the agent carry out the attacker’s i...
CIO Executive Brief #32 — Quantum vs. AI: The Strategic-Plan Collision No One Budgeted For
TL;DR
• Microsoft pulled its post-quantum cryptography deadline forward four years — from 2033 to 2029 — and Google and Cloudflare have set the same date. This is no longer one vendor’s roadmap; it’s a coordinated signal from the companies...
A quick correction — did you land on the right newsletter?
A short, honest note — housekeeping, not a regular Brief.
When I launched the Digital Safety Playbook back in May, I set it up in a way that accidentally subscribed some of you to this newsletter — the professional one — when what you actu...
CISO Executive Brief #32 — Your AI Security Framework Governs the Wrong AI: The Agentic Exclusion Nobody Read
TL;DR
• In April 2026, U.S. bank regulators issued SR 26-2, the first major update to model-risk governance since SR 11-7 in 2011. Buried in it is a sentence most security leaders missed: generative and agentic AI are explicitly excluded f...
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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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