Limited availability · Board & advisory engagements

AI transformation,
led by someone who
has already delivered it.

I'm Robert Kehoe — CTO, board advisor, and CISSP-certified cybersecurity leader. Twenty years steering engineering and security organisations through change, now focused on helping boards and executive teams navigate AI transformation and Cybersecurity with a clear-eyed view of both the opportunity and the risk.

Board Advisory → Proof of Work →
Robert Kehoe
Robert Kehoe CTO · Board Advisor · CISSP
Executive tenure
20+years · CTO & Head of Eng
Credentials
CISSP · ISC²
Current focus
AI transformation & governance
Availability
2NED / advisory seats
domains:AI transformation Cybersecurity governance Agentic product strategy Detection & response Board & audit readiness
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Board Advisory

● Accepting engagements

Most AI and cyber advice at board level is abstracted from delivery. I've spent two decades leading engineering and security organisations through transformation — and I'm still close enough to the work to tell the difference between a real agentic opportunity and a vendor pitch.

Engagements are structured around the decisions boards and executives face now: AI transformation roadmaps, cyber posture reviews ahead of funding or audit, technology strategy for agentic products, and regulatory exposure in AI-adjacent workflows.

A.01

AI transformation strategy

Roadmaps for boards and executive teams that separate genuine agentic opportunity from vendor theatre. Where to invest, where to wait, and how to measure progress.

A.02

Cybersecurity governance

Board-level oversight frameworks, risk reporting that reflects reality, and readiness ahead of regulatory, investor, or acquisition scrutiny.

A.03

Technical & AI due diligence

Pre-investment and pre-acquisition reviews of engineering organisations, security posture, and AI claims — with a view sharp enough to see through the deck.

A.04

Interim & fractional CTO

Executive technical leadership during transitions, scaling pressure, or post-incident rebuild periods. Senior judgement, available immediately.

— Who this is for
Scale-ups (Series B+) PE-backed portfolios Regulated sectors Financial services Health & data-intensive Pre-acquisition / IPO readiness
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Proof of Work

Advice grounded in delivery, not decks

The advantage I bring to the boardroom isn't theory — it's a track record of driving AI transformation and shipping agentic products inside real organisations. Below is a snapshot of what that looks like.

Track record

Executive delivery across engineering, security, and AI

As CTO and head of engineering, I've led organisations through product transformation, security maturity programmes, and the shift to AI-native product development. Current focus: helping leadership teams translate agentic AI from proof-of-concept into operational advantage.

AI product transformation
Led the design and delivery of agentic product lines in regulated environments — from strategy through to production.
Security programme leadership
Built and scaled detection & response functions across MDR and enterprise settings; CISSP-certified oversight.
Engineering organisation design
Structured and scaled engineering teams through Series B+ growth, M&A integration, and platform rebuilds.
Board & executive reporting
Translating technical and cyber risk into the language boards and audit committees can act on.
Domains

Where I work

Areas I know deeply enough to lead or advise with conviction.

Strategy
AI transformation
Engineering
Organisation design
Risk
Board & Cybersecurity
M&A
Tech, SasS & AI DD
Hands-on credibility

Still close to the work

I don't only talk about this — I'm actively building with it, so the advice stays current.

focus
Agentic workflows for security operationsProduction multi-agent systems augmenting analyst triage and investigation.
Active
focus
Detection engineering as a software disciplineCI-gated rule pipelines, evaluation harnesses, and platform-agnostic tooling.
Active
tools
Claude API · MCP · evaluation frameworksCurrent toolset — kept deliberately small and close to production.
Daily
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Writing & POV

Updated periodically — not a content strategy
AI & Agents 11 min

Claude Mythos and what it means for Organisations & BoD.

Apr 2026 ↗
AI & Agents 09 min

The agent evaluation problem: why 87% passing is worse than 40% failing loudly.

Mar 2026 ↗
Board & Governance 11 min

A cyber risk register that your board will actually read — and what to cut from the current one.

Jan 2026 ↗
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About

Cork · Remote-first · EU & UK

Two decades leading engineering and security organisations through change.

My career has moved between software engineering, cybersecurity, and executive leadership — typically in environments where regulation, adversaries, or scale made the margin for error small. That's shaped how I think about AI: cautiously optimistic, sharply practical.

What boards and executive teams get from working with me is senior judgement informed by current delivery. I still get my hands dirty with the technology I advise on, because the alternative — advising from a position outside the work — is how bad decisions get made.

certCISSP exp20+ yrs roleCTO · Head of Eng sectorRegulated · MDR · SasS
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Get in touch

Replies within 48 hours
Or reach me directly

Prefer email or a LinkedIn message? Both inboxes are mine and I read them. A couple of sentences on context is usually enough to work out a next step.

Email
robert@robertkehoe.com
→
LinkedIn
linkedin.com/in/robertkehoe
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Replies within 48 hours on weekdays. Based Cork · available across EU & UK time zones.