AI strategy assessment and setting
Where AI pays, what it may touch, and the controls that let a board say yes.
Sheet 01 · Home
Fractional CISO and CTO.
I take the audit, the cloud bill, or the AI rollout that is stuck, find the real cause, and get it to done.
Named work · Thirty years, at
- SentinelOne
- 2021 to 2026
- Nike
- 2016 to 2021
- RelayHealth
- 2014 to 2016
- Intel
- Late 1990s
- Silicon Graphics
- 1998 to 1999
- Bank of America
- Y2K remediation
- GoldMail
- Contract engineer, then CTO · 2006 to 2008
- Triverium
- Founder and CTO · 2012 to 2015
- 802 Secure
- Acting CTO · 2014
02 · Comparison
What changes when I take the seat.
Each row is tied to the record it comes from.
| The usual way | With Paul |
|---|---|
| A multi-year outside plan for the certification. | Scoped tightly to a hardened account. AWS Security Competency done directly, without the inherited two-year outside-firm plan.PV-2021 |
| SOC 2, SOX, and FedRAMP run as separate fire drills. | Driven together, in one program.PV-2021 |
| Cloud spend modeled as “it scales with agents.” | Real spend analysis found the savings in Presto and Kubernetes.PV-2022 |
| Security asks for budget with adjectives. | One benchmarked slide. The CFO challenged the method, then signed off on it. The largest CIS security-budget increase in Nike’s history.PV-2016 |
| AI bought as licenses, adoption left to chance. | Training, an approval flow, and token governance. Helped move 800+ people across engineering, product, sales engineering and IT onto AI-accelerated development in weeks.PV-2025 |
| Security as the team that says no. | Risk owners decide, inside the company’s risk appetite.PV-2016 |
03 · Services
What I do on an engagement.
Four services, each backed by the record.
Core issue diagnosis
The real cause, in writing, before anyone spends on a fix.
Architecture and delivery guidance for correction
The fix, sequenced, and the team that can run it after I leave.
Compliance acceleration
SOX, SOC 2, FedRAMP, and HIPAA on the business’s schedule, not the auditor’s.
04 · Engagement
Two ways to start.
Start with a fixed assessment, or put me in the seat.
Model A
Assessment
Focused and fixed scope on one of the four services. It ends in a written plan and a readout.
- Duration
- Typically 4 to 6 weeks
- Fee
- Credits toward the retainer if you continue
Model B
Retainer
Fractional CISO or CTO. I own the lane and work inside your leadership team.
- Time
- About a day a week
- Minimum term
- 3 months
Scoped and priced in writing after a 30-minute call.
How engagements are shaped05 · Proof
Track record.
Situation, objective, action, result, and how the work got led.
PV-2021 · Lead for compliance acceleration
SOX, SOC 2 and FedRAMP driven together. AWS Security Competency without the two-year plan.
- Situation
- Pre-IPO SentinelOne needed AWS Security Competency, FedRAMP Moderate recertification, SOC 2 Type 2, and a SOX audit, with about 18 months to do it.
- Objective
- Land all four on that clock, without the inherited two-year outside plan.
- Action
- Replaced the outside-firm plan, filled in the Competency paperwork directly, and scoped it to a hardened AWS account. Drove SOX, SOC 2, and FedRAMP through alongside it.
- Result
- SOX, SOC 2 Type 2 and the FedRAMP Moderate recertification came through. AWS Security Competency announced October 13, 2021, which put SentinelOne on the AWS Marketplace.
How it was led
- Approach
- Scope a certification tightly to a hardened account.
- Partnership
- Helped the future CISO build the diagnosis and the proposed fixes before I joined.
- Influence
- Built the first real cloud spend analysis, where the working model had been that spend scales with deployed agents.
- Delivery
- The planned two-year landing zone migration, bypassed.
- Dwg
- PV-2021
- Org
- SentinelOne
- Period
- 2021 to 2022
- Seat
- Senior Director, Cloud Operations
PV-2025 · Lead for ai strategy assessment and setting
AI adoption, gated and governed
- Situation
- A CEO initiative to put SentinelOne on an AI coding tool. Onboarding a new vendor usually took 3 to 6 months.
- Objective
- Windsurf acquired, onboarded and in daily use fast, with about 800 seats and gated access.
- Action
- Pushed 30+ people across finance, compliance, IT, procurement, and security to move fast. Wrote the training, the approval flow, and the token governance.
- Result
- Procurement in under a month. Helped move 800+ people across engineering, engineering managers, product managers, sales engineers, IT and other staff onto it in weeks.
- Approach
- Instrument the counterfactual, or you will read the gain backwards.
- Partnership
- Ran the training with the Coralys training team and the AI Champions program.
- Influence
- Opened group trainings with my own history, vi to IDE to debugger, so the tool read as the next step in developer tooling, not a replacement.
- Delivery
- The unit test coverage bar met across most of the codebase within weeks.
- Dwg
- PV-2025
- Org
- SentinelOne
- Period
- 2025 to 2026
- Seat
- Principal Infrastructure Engineer
PV-2016
A board-level budget case, a mission, and a BizOps function for Nike CIS.
- Situation
- Nike CIS budget asks came back smaller than requested, and mid-year give-backs were handled one Senior Director at a time, with no shared target.
- Objective
- Fund security at a level benchmarked to Nike’s industry and revenue, and give CIS control of its own budget, buying and delivery.
- Action
- With the other strategists, built CIS its own BizOps function. Designed the Quick Wins process, and built one benchmark slide setting CIS budget against industry security spend, adjusted for Nike’s revenue.
- Result
- The largest CIS security-budget increase in Nike’s history. The CFO challenged the benchmark method, then signed off that it was accurate.
- Approach
- Turn a budget ask into a governance lever.
- Partnership
- Wrote the CIS mission with review from two senior CIS individual contributors.
- Influence
- Budgets are board-approved, so the benchmark made the CIS budget a governance and fiduciary question for the board.
- Delivery
- Four multi-year strategies, reviewed quarterly and driven to the CISO.
- Dwg
- PV-2016
- Org
- Nike
- Period
- 2016 to 2019
- Seat
- Expert Cyber Security Strategist, Nike Corporate Information Security
06 · How I work
A fractional seat that works like a full one.
Access
The person on the call is the person who does the work.
- Replies within 24 hours.
Knowing the team
- SentinelOne’s first CISO was given Cloud Ops and invited me in as Senior Director of Cloud Operations.PV-2021
- GoldMail’s CFO is today, through CXOSI, my most active channel for fractional and advisory work.Bleenq
- Advised director Michael Mann on the film Blackhat, then secured his company, 2013 to 2016.Forward Pass
Building it with you
- Helped SentinelOne’s future CISO build the diagnosis and the proposed fixes before I joined.PV-2021
- Wrote the Nike CIS mission, reviewed by two senior CIS individual contributors and adopted by the CISO without changes.PV-2016
- Pushed 30+ people across finance, compliance, and security to move fast, and onboarded a vendor in under a month.PV-2025
07 · Book
Bring the problem.
Leave with the next three moves.
- Length
- 30 minutes
- With
- Paul, directly
- Reply
- Within 24 hours
- After
- Scoped and priced in writing after a 30-minute call.