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Webinar replay

5-Minute
vCISO Prep Skill

A free AI skill that turns last call's notes, tickets, and client emails into a client-ready cadence call agenda. Built with a working vCISO, so it writes like one.

Recorded live on October 8, 2026.

Jesse Miller
Jesse MillerCreator of the PowerGRYD vCISO System

Get the skill

Enter your email and we'll send you the 5-Minute vCISO Prep Skill. You get a .skill file for Claude, ChatGPT, or the LLM of your choice, plus an .md version for Lexful.

Watch the replay

Jesse walks through the skill on a sample client, refines it as he goes, then reviews the finished itinerary section by section and answers questions.

What's covered

  • What makes a skill worth using: one specific job, done with real expertise behind it
  • The four vCISO meetings, and why the cadence call is the one this skill preps
  • Why the vCISO role is advisory, and why the skill asks you instead of guessing
  • The finished itinerary, section by section: headlines first, OKRs, current tasks, hot stove items, and future items
  • Why the itinerary works as a discoverable, due-care business record
  • Q&A: context sources, call transcripts, explaining skills to clients, starting a vCISO program, and the .skill and .md files
Get the skill

The problem

Advisory work is hard, and the unseen work is what trips most MSPs up. Having a bulletproof plan for your program's cadence calls is what actually makes or breaks the contract.

Prepping properly takes 30 to 60 uninterrupted minutes, and your client can tell when you skip it. Generic AI makes it worse, happily writing "all risks accepted" into the record when that call belongs to a client executive.

The itinerary is the business record of the security program, discoverable and all. That document deserves real preparation, every single week.

What it does

Five minutes of prep, start to finish.

Makes your client feel like you spent hours on the account.

Scans your emails, tickets, and last call's itinerary for what belongs on this week's agenda
Carries the record forward: tasks, owners, due dates, dated updates, nothing dropped
Writes in a vCISO's voice: measured entries, advisory framing, zero risk determinations you never made
Ends with a pre-call brief that prepares you and gives you coaching and consensus-building talking points.
vCISO Cadence Call

Cedarline Fabrication, Inc.  ·  25 August 2026

Stakeholders
NameRoleOrganization
Victor ReyesClient SPoC; Director, ITCedarline Fabrication, Inc.
Diane OkaforClient Executive Sponsor; COOCedarline Fabrication, Inc.
Sam WhitfieldClient Compliance OfficerCedarline Fabrication, Inc.
Nora QuinnvCISORidgeline Security
Security Program: Objectives
  • Risk reduction to 42% by year-end
    Supports margin stability by lowering the chance of unforecasted incident spend.
  • CMMC Level 2 readiness, assessment targeted Q1 2027
    Protects the defense revenue line and supports winning two new defense primes.
  • Incident Response Plan published and exercised
    Reduces the cost and disruption of security events.
Current Tasks
StatusOwnerTaskDue
Past-dueSam WhitfieldConfirm CMMC assessment scope with prime contractor.21 Aug 2026
In-progressNora QuinnDraft incident summary for the insurance carrier with caveat language.26 Aug 2026
In-progressDiane OkaforSocialize security budget adjustment with CFO ahead of Q4 planning.28 Aug 2026
To-doElena NovakComplete OT asset reconciliation for the two hosts missing serials.[date?]
Hot Stove Items

Business Email Compromise Incident (AP and Purchasing Mailboxes)

  • 19 Aug 2026Ad-hoc incident review held. At this point there is no indication sensitive data was accessed; the mailbox content review is ongoing, with the forensics vendor engaged.
  • 21 Aug 2026Victor completed the tenant-wide mailbox rules audit. No additional hidden rules identified to date; monitoring continues.

Board Pre-Read Incident Briefing

  • 20 Aug 2026Diane requested a one-page, plain-English incident briefing she can lift into the board pre-read distributing 03 Sep.
Updates

Incident Response Plan

  • 11 Aug 2026Executive sign-off received. The tabletop exercise remains open and ownership for scheduling it still needs to be assigned.
  • 19 Aug 2026Plan has been published to the organization. The incident comms template still carries an outdated distribution list.

CMMC Level 2 Readiness

  • 28 Jul 2026Gap assessment complete. 31 of 110 practices need remediation or documentation.
  • 19 Aug 2026Calvert scheduled the scope call for 27 Aug 2026 and will bring the flow-down matrix to settle which CUI touchpoints are in scope.

How it works

STEP 1

Add the skill to Lexful, Claude, ChatGPT, or any LLM of your choice. In Lexful, add the .md file in Settings, then Skill Library, and call it from Ask Lex.

STEP 2

Point to last call's itinerary and whatever materials you want to reference.

STEP 3

Review the output, walk into your vCISO meeting prepared, and give your client a high-value experience every time.

The lineup

Who you'll hear on the replay

Jesse MillerJesse Miller
Creator of the PowerGRYD vCISO System
Kevin CluneKevin Clune
Founder, MSP Growth Hacks
Eric PerezEric Perez
Growth Marketing Manager, Lexful