The Interim CISO for the Board's Worst Day
I'm brought in when reassurance has failed.
- Board-level cyber failure or regulator pressure
- Interim authority required, not advisory noise
- You already know the cost of getting this wrong
If you're looking for vendor selection, tool comparisons, or compliance checklists—I'm not the right advisor.
My work is designed to withstand regulatory hindsight.
5-Minute Board Summary
Who I Am
27 years in cybersecurity. 21 years in financial services. Experience across all Big 4 firms. Advisor to boards overseeing $500B+ in assets. Expert witness in UK/EU financial litigation.
When I'm Called
Following material breaches, regulatory intervention, failed transformation programmes, or pre-deal cyber due diligence. Typically post-incident, when internal teams need external authority.
What I Deliver
90-day stabilisation. Board-ready risk reporting. Regulator-defensible remediation plans. Operational continuity during crisis. Institutional knowledge transfer at exit.
How to Engage
Next availability: Q3 2026. 2–3 advisory engagements per year. Typical engagement: 90-day interim CISO or board advisory retainer. Contact via secure channels below.
What Most Boards Get Wrong About Cyber Risk in 2026
They treat cyber as a technology problem
Cyber risk is a business continuity problem. The board that asks "are we secure?" is asking the wrong question. The right question: "If we're breached tomorrow, can we still operate, and will regulators accept our response?"
They confuse compliance with resilience
DORA and NIS2 are not checklists. They're frameworks for demonstrable operational resilience. Most firms will pass audits and still fail incidents. The gap is judgment, not controls.
They underestimate the speed of AI-enabled threats
Attackers are already using AI to accelerate reconnaissance, craft phishing, and automate exploitation. Defenders are still writing policies. The asymmetry is widening, not closing.
These are the conversations I have with boards. If your current advisors aren't raising these questions, we should talk.
Request a Board Briefing
Kieran Upadrasta, CISSP
CISO and Founder of Cyber Artificial Intelligence Systems Inc. Expert witness in UK/EU financial services litigation. Advisor to national cyber defence initiatives (non-public roles).
27 years in cybersecurity. 21 years in financial services. All Big 4 firms. Advisory work with boards overseeing $500B+ in aggregate assets.
Areas of Specialisation
Deep expertise across the critical domains that define modern enterprise security and risk management.
DORA Compliance
Digital Operational Resilience Act expertise. ICT risk management, incident reporting, and third-party governance for European financial services.
AI Governance & ISO 42001
AI Security Design Authority specializing in responsible AI frameworks, EU AI Act compliance, and enterprise AI risk management.
Zero Trust Architecture
Enterprise Zero Trust frameworks on Azure, AWS, and GCP. 40+ successful migrations across complex multi-cloud environments.
Board Reporting
Translate complex cyber risk into board-ready language. Develop metrics, reporting frameworks, and executive communication strategies.
M&A Cyber Due Diligence
Technical security assessments for mergers and acquisitions. Identify hidden cyber risks before they become expensive liabilities.
NIS2 Directive
Network and Information Security Directive compliance. Critical infrastructure protection and security requirements for essential services.
Skills Matrix
Comprehensive expertise across enterprise security domains, platforms, and technologies.
Security Architecture & Strategy
Identity & Access Security
Risk Management
Threat & Vulnerability Management
Governance, Risk & Compliance (GRC)
Cybersecurity Platforms
Standards & Assurance
Data Protection & Insider Threat
Cloud & DevSecOps
Security Operations & SIEM
Network, Endpoint & Perimeter
Regulatory & Government
Core Specializations
How Engagements Actually Begin
Something has failed
A breach. A failed audit. A departure. A regulator letter. Internal teams are stretched. The board needs external authority.
A referral is made
A NED who's seen this before. A law firm advising on exposure. A regulator-adjacent contact. I don't advertise. Work finds me through reputation.
A conversation happens
30 minutes. Secure channel. No pitch deck. If the problem is one I can solve, and I have availability, we discuss terms. If not, I refer to trusted peers.
I take 2–3 engagements per year. If this sounds like your situation, the form below will reach me directly.
Case Studies
Quantifiable results from enterprise security transformations across financial services and critical infrastructure.
Post-Breach Stabilisation
Tier 1 financial institution. Major breach discovered. No security leadership. Established command and restored stakeholder confidence within 90 days.
Regulatory Readiness
€2B AUM asset manager with minimal security function. Built comprehensive ICT risk framework achieving full DORA compliance ahead of deadline.
Enterprise Migration
Global insurer with 15,000 endpoints across 12 countries. Designed and implemented Azure-native Zero Trust architecture with zero disruption.
How I Help Boards
Interim CISO
Immediate executive leadership. Establish command within 90 days. Stabilise post-breach environments and build sustainable security programmes.
AI Risk Advisory
AI Security Design Authority services. ISO 42001 implementation. EU AI Act readiness. Responsible AI governance frameworks.
DORA & NIS2 Compliance
Digital Operational Resilience Act and NIS2 Directive readiness. ICT risk management, incident reporting, and third-party governance.
Zero Trust Architecture
Enterprise Zero Trust frameworks on Azure, AWS, and GCP. Evidence-based blueprints from 40+ successful migrations.
M&A Due Diligence
Technical security assessments for mergers and acquisitions. Identify hidden cyber risks before they become liabilities.
Board Advisory
Translate complex cyber risk into board-ready language. Develop metrics, reporting frameworks, and executive communication strategies.
Not the Right Fit For
To ensure maximum value for clients, I focus exclusively on strategic, high-stakes engagements. This practice is not suited for:
Problems I'm Brought In For
How Peers Describe My Role in Crises
"When our CISO departed mid-breach, Kieran was the only name that came up twice in the same conversation—once from our lawyers, once from a NED. That doesn't happen by accident."— Former Group CRO, European Investment Bank
"I've worked alongside Kieran on three separate regulatory responses. He understands how regulators think because he's been on both sides of the conversation."— CISO, FTSE 100 Financial Services
"Most consultants deliver slides. Kieran delivers operational stability. There's a reason he's the person firms call when they can't afford a learning curve."— Partner, Global Law Firm (Cyber Practice)
"Quoted in confidence by a FTSE Chair following a post-incident regulatory review: 'Kieran was the steadiest hand in the room when we needed it most.'"— Regulatory submission documentation, 2024 (client permission granted)
Names withheld at peer request. References available upon serious inquiry.
What Leaders Say
Kieran brought clarity to our board on cyber risk like no one before. His ability to translate technical complexity into strategic language transformed how we approach security investment decisions.
Post-breach, we needed someone who could stabilise fast and communicate with confidence. Kieran established command within weeks and rebuilt stakeholder trust across the entire organisation.
Verified on Request
Full credentials, certifications, awards, and detailed accomplishments are available to regulators, courts, and boards conducting due diligence.
CISSP • CISM • CRISC • CCSP • ISACA Platinum • ISC² Gold • University Gold Medal (UCL)
Request Full CredentialsPublications & Research
Strategic frameworks, white papers, and research spanning AI governance, cybersecurity, and regulatory compliance.
Strategic Frameworks & White Papers
Harmonizing DORA and NIS2: Unified Resilience Framework
A Strategic Framework for Boards, CISOs, Risk Committees, and Supervisory Authorities. Research across 47 European financial institutions revealing 75-95% control overlap.
Read White Paper →The Sovereign Zero Trust Model
Data Immunity and Supply Chain Resilience in 2026. The Third Maturity Phase: Identity → Access → Resilience. Featuring The Upadrasta Index™: Proprietary Research on Cross-Border Recovery Capability.
Read on Slideshare →THE CISO'S 2027 PLAYBOOK
Sovereign AI Resilience & Quantum-Proof Identity. Building the Apex Architecture for Non-Linear Threat Convergence.
Read on Slideshare →COMMANDING THE CRISIS
An Interim CISO's 90-Day Roadmap to Boardroom Confidence. The definitive playbook for establishing security command during crisis.
Read on Slideshare →ARCHITECTING THE AI CONTROL PLANE
From Perimeter to Portfolio: Enterprise Governance for the Agentic Era. The Definitive Framework for Board-Level AI Risk Governance.
Read on Slideshare →From Compliance to Competitive Advantage
Board-Level Cyber Governance Under DORA and NIS2. Transform Regulatory Compliance into Enhanced Valuations, Reduced Cost of Capital, and Accelerated M&A Outcomes.
Read on Slideshare →Governing the Agentic Enterprise
From Shadow AI to Autonomous Security. A Strategic Framework for Board-Level AI Agent Governance, Machine Identity Security and Regulatory Compliance.
Read on Slideshare →THE BOARDROOM CYBER PLAYBOOK
Governance, Resilience, and Value Creation. A Research-Based Strategic Guide for Directors and Executives.
Read on Slideshare →The Azure Zero-Trust Blueprint
From Compliance Mandate to Competitive Advantage in the AI Era. How Boards, Regulators, and CISOs De-Risk AI, Supply Chains, and Identity at Scale. Evidence-Based Insights from 40 Enterprise Migrations.
Read on Slideshare →The AI-Driven Threat Frontier
Zero Trust, Identity & Supply Chain Resilience. A Security Leader's Roadmap for 2026 and Beyond.
Read on Slideshare →The CISO Transformation Playbook
From Cost Centre to Chief Trust Officer. Transform Regulatory Compliance into Revenue Enablement, Board-Level Influence, and Measurable Business Value Under DORA and NIS2.
Read on Slideshare →THE SOVEREIGN COURTROOM
Scaling Azure AI for Resilient Legal Operations. Board Governance, Regulatory Compliance, and Enterprise Implementation.
Read on Scribd →ARCHITECTING CLOUD-NATIVE AI STACKS
A Strategic Framework for Migrating .NET to Python-React. Board-Level Decision Guide | Evidence-Based Methodology | Risk-Managed Execution.
Read on Slideshare →THE SAP PAYROLL TRANSFORMATION PLAYBOOK
Mitigating Risk and Maximizing Value in Multi-Workstream HRIS Transformations. A Technical Blueprint for 2025-2026 with AI Governance, TCO Analysis & Hypercare Framework.
Read on Slideshare →Media Coverage & Recognition
The Cybersecurity Pioneer Fueling Innovation
Exploring AI in digital security, analyzing how algorithms predict and prevent cyber threats.
Read Feature →Visionary Leader in Cybersecurity
Career profile covering 27 years of cybersecurity experience and Big 4 consulting.
Read Profile →Honorary Doctorate in Literature
Recognition for contributions to cybersecurity, AI, and quantum computing.
Read Announcement →Renowned Cyber Security Expert
Expert in incident response, crisis management, and stakeholder engagement.
Read on Benzinga →25 Years as Cyber Security Architect
Career milestone coverage: information security consulting and risk management.
Read on Digital Journal →What I'm Watching Q1 2026
Contrarian positions based on 27 years of pattern recognition. Not predictions—observations about where the herd is wrong.
Why 30% of EU Banks Will Fail DORA First Wave
Most compliance programmes are focused on documentation, not operational resilience. When ESMA starts testing, the gap between "compliant" and "resilient" will become painfully visible. The banks that treated DORA as a checkbox exercise will discover their third-party dependencies are still single points of failure.
Position taken: January 2026The First Material AI-Enabled Breach Is Closer Than You Think
Attackers are already using LLMs for reconnaissance and spear-phishing at scale. Defenders are still writing policies. The asymmetry will produce a landmark incident—likely in financial services—where AI wasn't the vulnerability but the weapon. Boards will be asked why they didn't see it coming.
Position taken: January 2026Cyber Will Become a Board-Level Insurance Issue by Q4 2026
D&O insurers are quietly rewriting policy language around cyber governance. Within 12 months, board members without demonstrable cyber oversight will face personal liability exposure that no indemnification can cover. The smart NEDs are already demanding evidence of operational resilience—not just strategy decks.
Position taken: January 2026These are personal observations, not advice. If your organisation is navigating any of these areas, I'm available for confidential conversation.
Frameworks & Templates
The 90-Day Post-Breach Playbook
Board Edition — Used in Tier 1 financial services incidents
Stabilisation
Establish command, contain scope, secure evidence, brief board
Assessment
Root cause analysis, regulator communication, stakeholder management
Remediation
Control implementation, resilience testing, exit criteria, handover
This framework has been used in material incident responses across European financial institutions. It is not a checklist—it is a decision architecture.
I'm brought in when reassurance has failed.
Request the Full Playbook
The complete 90-Day Post-Breach Playbook includes detailed decision trees, board communication templates, and regulator liaison frameworks.
Request AccessLet's Secure Your Future
For interim CISO engagements, board advisory, AI governance, DORA compliance, or strategic security consultations.
I do not offer ongoing managed services, virtual CISO retainers, or tool implementation.
Dublin, Ireland
Initiate Contact
Messages are read personally. If this isn't the right fit, you'll be referred onward.
Response within 48 hours. Secure channel (Signal/Wire) available on request.