Independent CIO & board advisory

When technology needs a decision. Or someone accountable.

For boards, CEOs and founders facing a leadership gap, rising technology costs or a consequential cyber or AI decision. I bring the judgement of a former Group CIO, working directly with you to decide what matters and take it forward.

Fractional or interim leadership. A defined independent review. Singapore-based, global remit.

Discuss an engagement Compare engagements

Michael Kennedy · Former Group CIO, Robert Walters
CISSP · IAPP AIGP · No vendor commissions
MSc Cybersecurity with Artificial Intelligence (in progress)

Michael Kennedy, founder of Kennedy Advisory

Services

Choose the help your situation needs.

Independent technology leadership for boards, executive teams, founders and PE-backed companies — Singapore-based, engaged globally.

I take no referral fees, no vendor commissions and no reseller margin. My only revenue is the fee you pay me, and I’ll send standard terms before anything starts.

You need someone accountable

Fractional & Interim CIO

Senior leadership for a CIO gap, a stalled transformation or a technology function that needs a clearer direction.

Shape: 1–3 days a week, or full interim cover. Mandate, authority, duration and fee are scoped around the situation.
What to define together: Immediate priorities, a delivery and governance cadence, decision rights and the handover required.

Fit, inputs & boundaries

Role & scope: Lead the operating model, priorities, service quality, vendors, cyber and AI governance with your executive team.

Bring the leadership gap, current priorities, reporting line and key constraints. This is senior leadership, rather than an outsourced help desk. Team capacity, specialist work and implementation responsibilities need to be explicit in the scope.

Discuss leadership cover

You need an independent decision

The Technology Ledger

A defined board-level review of technology risk, cost, capability and AI posture before a consequential decision.

Shape: Three weeks. About nine hours of your team’s time. A fixed scope and fee agreed before starting.
What you receive: Five written deliverables, including a prioritised action list and board summary, with a findings discussion.

Fit, inputs & boundaries

Role & scope: Examine the evidence, challenge assumptions and explain the priorities and options to the board or leadership team.

Needs documentation, contracts, interviews and a named coordinator. It is not ongoing CIO cover, a penetration test, a code audit or a complete estate inventory. An urgent leadership enquiry can go directly to CIO cover.

Explore the Ledger

You need a clearer way to run technology

Technology Operating Model Review

A focused review when decision ownership is blurred, teams and suppliers work at cross-purposes, or service performance and cost no longer match what the business needs.

Shape: Duration, fee and breadth agreed around the question, the parts of the organisation involved and the evidence in scope.
What you receive: A current-state assessment, target operating model and prioritised transition roadmap. Proposed responsibilities, decision rights and governance arrangements are scoped review outputs for your decision.

Fit, inputs & boundaries

Role & scope: Assess how technology is organised and run, and define a target operating model for the agreed part of the function.

Review focus: decision rights and accountability; teams and capabilities; service delivery; supplier interfaces; governance; service performance and cost.

Inputs: current organisation and responsibilities, supplier arrangements, service measures, cost information and the people closest to delivery. The exact evidence and interviews depend on scope.

Fit: boards and executive teams deciding how their technology function should operate. Enter directly, or follow a Ledger where a deeper operating-model review is useful. No prior paid diagnostic is required.

Boundaries: technology operating model only. This is not company-wide restructuring, employment decisions, legal advice, standalone certification or operational implementation. The client retains operational responsibility and decides whether to adopt proposed changes.

Discuss an operating model review

You need a defensible vendor decision

Vendor & Enterprise Readiness

Independent challenge for buyers selecting a vendor, or preparation for vendors facing enterprise scrutiny.

Shape: Two to four weeks, scoped up front. Start by agreeing which side of the decision you represent.
What to define together: The decision, evidence to review, gaps to resolve and written findings needed for the buying or readiness process.

Fit, inputs & boundaries

Role & scope: Buyer: examine vendor evidence, risk and commitments.
Vendor: identify gaps in security and procurement readiness.

Bring the selection criteria or enterprise questionnaire, supporting evidence and decision deadline. Readiness does not guarantee procurement acceptance or certification. Legal opinions, testing and delivery beyond the review need their own scope.

Discuss buyer or vendor needs

Need leadership now? Start with CIO cover. Need a broad diagnosis? Start with the Ledger. Need a focused review of how technology is organised and run? Choose the Operating Model Review directly. For a buyer or vendor decision, choose readiness work. If the route is unclear, describe the situation in a first conversation.

Relevant disciplines, selected to fit the agreed engagement: ISO/IEC 27001 and board-level cyber accountability · AI governance and assurance · service excellence and ESM (SLA → XLA) · operating model, shared services and vendor consolidation · technology due diligence.

A defined independent review

The Technology Ledger

One honest picture of your technology — risk, cost, capability and AI posture — inside three weeks. Fixed scope, a fee agreed before we start, and a session at the end to walk you through what I found.

Built for boards and founders who

Need an independent view before deciding how to fill a CIO gap or restart a stalled transformation. For immediate cover, go directly to leadership.
Need to give the board assurance on cyber or AI before a regulator, an incident or an enterprise buyer forces the question.
Are watching technology cost and service quality drift, without knowing which lever actually moves it.
Are about to invest, acquire or be acquired, and want an independent read before the money moves.
Have been told it’s all fine for two years, and no longer quite believe it.

3weeks, start to finish

~9hours of your leadership team’s time, in total

5written deliverables, not a slide deck

Discuss an engagement

One fixed fee, agreed before anything starts. Scope, access needs and terms agreed before work starts.

How it works

Week one

Listen

Structured interviews — CEO, CFO, the technology lead, and two or three of the people actually doing the work
The board papers, the risk register, the last audit, the contracts
What has been promised, to whom, and by when

About 4 hours of your team’s time

Week two

Examine

Architecture, cloud and data estate at the level a board needs — not a diagram nobody reads
Security posture against ISO 27001 and the questions an enterprise buyer or regulator will ask
AI inventory — what is in production, what is in a sandbox, and what nobody has mentioned
Vendors and spend — what you pay, what you get, what you are locked into

About 3 hours of your team’s time

What I need: read-only access to your documentation, one named coordinator, and the contracts. What this is not: a penetration test, a code audit or a full estate inventory. It is a board-level read on what is true and what it will cost you.

Week three

Report

Findings written up and tested with you for accuracy before anyone else sees them
Everything prioritised, costed and given an owner
A 60 to 90 minute session to walk through the findings and take the hard questions — with your board or leadership team if that helps, or just with you

About 2 hours of your time

What you walk away with

Current State Ledger

One honest picture of technology risk, cost, capability and AI posture — the version without the optimism.

Risk Heatmap

What could actually hurt you, ranked by impact against the effort to fix it. High impact and low effort is your Monday list.

Cost & Vendor Findings

Costs and vendor commitments examined against the agreed scope, with findings, estimates and assumptions made clear. The scope and fixed fee are agreed before the engagement starts.

Prioritised Action List

Costed, sequenced, with owners and dependencies. Executable from the week after, not aspirational.

Board Summary

Two pages your board will actually read. Present it yourself, or bring me in — whichever suits how you work.

A written report, and a proper conversation about it. Not a slide deck, and not a proposal for more work.

Track record

What this has looked like in practice

More than 25 years of it, most recently as Group CIO at Robert Walters. Four examples from my employment at Robert Walters, and the same disciplines I bring to advisory work. These are career outcomes, not Kennedy Advisory client results. Professional background on LinkedIn (new tab)

25+

Years of global technology leadership

Countries, 23 offices, one operating model

£3M+

Annualised savings delivered

150+

Global technology organisation led

Operating model

A blueprint the whole group adopted

Designed and led a global shared-services operating model across 14 countries and 23 offices — subsequently adopted as the group’s Business Services blueprint, well beyond technology.

Outcome: adopted as the group’s Business Services blueprint, beyond technology.

Cost & vendors

Grip on spend, without degrading service

Consolidated the global vendor estate by ~40%, renegotiated key contracts and put technology spend under genuine executive control — while service performance improved, not slipped.

Outcome: Recurring annualised savings delivered during my tenure.

Governance & AI

Security and AI made board-ready

Took ISO/IEC 27001 across every jurisdiction, established board-level cyber accountability, and brought AI into production with human-in-the-loop controls — not pilots that never ship.

Outcome: clean audits in 14 jurisdictions, and a board that could answer the cyber question.

Service excellence

Service quality the business could feel

Transformed a distributed global service organisation — experience-level agreements (XLAs) implemented alongside SLAs, so service was measured by the experience people actually had, not just process compliance.

Outcome: Service Desk Institute accreditation, with XLAs live in production.

In their words

From the people I worked with for sixteen years

Kennedy Advisory launched in 2026 and current engagements are under NDA, so these are from Robert Walters — the people who saw the work up close, including the executive I reported to. I’ll talk you through live engagements on a call, and two named referees will take one.

Credentials belong to Michael as an individual. View credential links and how the practice handles information →

“

An outstanding technology executive with the rare combination of strategic vision, operational excellence, and inspirational leadership… he has consistently delivered results — from transforming our global IT operating model to strengthening security and driving innovation — all while building a strong team culture founded on trust, accountability and growth.

Dominic DowChief Technology & Product Officer, Robert Walters Group — Michael’s direct manager

“

A visionary CIO with a strong commercial mindset and a clear ability to align technology with business outcomes. He consistently blends strategic thinking with practical delivery and sound judgement.

Chris AllenServices Director, Robert Walters

“

He has a rare ability to cut through complexity, focus on what truly matters, and consistently deliver value for the business… Any organisation would be fortunate to have Michael leading their technology function.

Robert CrossTechnology Leader, CISSP

Writing & building

Still in the work, not just advising on it

Most of what I advise on, I’m also doing. A book published this year, and products I continue to build and test.

Book · Published September 2026

The Full Ledger

Governing the True Footprint of Technology

Every cloud region selected, every AI model deployed, every dataset retained creates footprint — energy draw, water use, embodied carbon, inference cost. Yet it gets measured everywhere except where the decisions are actually made: in sustainability reports, far from the architecture forums and procurement reviews.

Not a sustainability manifesto. A governance book — a measurement framework, decision gates that fit the forums you already run, and board reporting that earns attention the way security once did.

View on Amazon

Inside

The Full Ledger Framework — eight dimensions of technology footprint, and how to measure each
The Invisible Footprint Audit, and the Accepted-Risk Script
Decision gates that fit existing architecture, AI, data and change forums
Board reporting structures, model curves and region profiles
The regulatory floor now arriving — the EU Energy Efficiency Directive and the disclosure wave
A 90-day starting plan, and a full implementation roadmap

Focuses on realistic governance rather than preaching about sustainability. The frameworks and examples feel genuinely useful for technology leaders.
Amazon reviewer, UK

The ‘ledger’ is not just a metaphor but a framework for tracking the social, environmental and ethical costs that often remain hidden.
Amazon reviewer, UK

Written from a CIO’s perspective, it focuses on real-world governance rather than abstract sustainability manifestos. Easy to jump straight to the chapters you need.
Amazon reviewer, UK

Essays

The Duty of Care · Part 1

Are We Treating People Merely as Means?

Most AI governance starts — and too often ends — with an outcomes test: will it work, and do the benefits outweigh the harms? The harder question sits underneath. On turning Kant’s principle into working design disciplines, and one personal test: authorise only the architectures you’d be willing to live inside.

Read on LinkedIn

The Duty of Care · Part 2

Why Green IT Is an Accounting Problem, Not a Values One

The honest case for Green IT isn’t a values appeal, it’s an accounting one. Put technology’s energy, carbon and waste on the books — where IT sits in SGX climate reporting, the rising AI energy bill, the six levers that cut cost and carbon together — and it becomes a decision a board can actually make.

Read on LinkedIn

An evolving series on the duty of care in technology. Follow on LinkedIn to catch new essays first.

Products & creative work

From idea to working product.

I design each product and take it through development, automated testing and release, using multi-model AI tools as part of the build process.

01 / Youth football academy platform

Trust The Process

Ongoing academy trials · UK & Singapore

A development record for each player: plans, released coach feedback and confirmed match information. Scheduling, attendance and family updates bring academy workflows together.

Explore TTP (new tab)

02 / Singapore conditions app

HazeWatch

TestFlight

Air quality, lightning and heat stress for the places you save, built on NEA open data. Conditions, alerts and shareable cards for home, school or the pitch.

Explore HazeWatch (new tab)

03 / Family command centre

FamilyDay Hub

A shared household calendar, chores, study plans and rewards, with a kitchen iPad display and an AI family briefing. One place for the family to see what comes next.

Explore FamilyDay Hub (new tab)

04 / Discipline challenge app

Proving

Private beta

Goal-based 40, 75 or 90-day challenges with Apple Health, photo, partner and self-reported evidence. An Integrity Score distinguishes proven work from ticked boxes.

Explore Proving (new tab)

Official product image

05 / Bill-splitting platform

CanSplit

Live web · iOS TestFlight

Singapore bill splitting with receipt recognition, itemised or equal splits and multi-currency settlement. PayNow QR codes show each person’s share.

Explore CanSplit (new tab)

06 / Multiplayer quiz platform

ClanQuiz

Web & Apple TV · TestFlight

Family quizzes and PSLE revision, with varied question formats, picture clues and phones as controllers. Bring the family together around the TV.

Explore ClanQuiz (new tab)

07 / Family party games

Duelville

TestFlight

Quick party games for two to four players sharing one iPhone, including Tank War and golf. Destructible terrain, a running score and no ads.

Explore Duelville (new tab)

08 / Online store & YouTube

CaledonianRoots

A Scottish heritage store for clan and tartan designs, alongside a YouTube channel of 4K Scotland films. A creative portfolio spanning print-on-demand, digital products and video.

Visit the online store (new tab)Watch on YouTube (new tab)

Which is why, when I’m advising on AI-native product, data consent or platform risk, it comes from current practice rather than memory. I also package the governance frameworks I use into board-ready toolkits, for teams who would rather run them themselves.

About

A global CIO, now independent

Credentials

—Former Group CIO, Robert Walters
—25+ years, global technology leadership
—CISSP, (ISC)²
—AIGP — AI Governance Professional, IAPP
—MSc Cybersecurity with Artificial Intelligence (in progress)
—CTO Programme, National University of Singapore
—ITIL Expert · PRINCE2 · MBCS
—Singapore Permanent Resident

Discuss an engagement

I started on mission-critical systems in a high-security nuclear research environment, and spent the next three decades in places where technology failing was not an option — regulated financial services, 24/7 online platforms, then sixteen years at Robert Walters across the UK, Europe and Asia. Singapore-based since 2008, with a global remit throughout.

The arc

2024–26Group CIO, Robert Walters — Singapore, global remit

2017–24Director of Technology Operations, Robert Walters — built the global shared-services model

2010–17IT Director & APAC leadership roles, Robert Walters — built the region’s technology capability

2009IT Operations Manager, F&C Asset Management — regulated financial platforms, Edinburgh

2006–08Infrastructure & Systems Manager, Mansion Group — 24/7 online gaming platforms, Gibraltar / Singapore

2004–06Technical Services Manager, Savcor — infrastructure and end-user services, Scotland

1997–2004Server Manager, UK Atomic Energy Authority — mission-critical systems in a high-security nuclear research environment

1996–97Omnes (Schlumberger) — enterprise messaging across UK / US oil & gas operations

Before you engage

A few practical questions.

Do I need a Ledger before engaging a CIO?

No. If you need immediate fractional or interim leadership, discuss that directly. The Ledger is a separate route for an independent review before a decision.

How does the Operating Model Review differ from the Ledger?

The Technology Ledger gives a broad picture of technology risk, cost, capability and AI posture, with priorities for a decision. The Technology Operating Model Review goes deeper into how the technology function should be organised and run, with a current-state assessment, target operating model and prioritised transition roadmap. It can be a direct entry or follow a Ledger where appropriate. Fractional or interim CIO cover provides ongoing accountable leadership. A Ledger is not a prerequisite for either.

How are scope and fees agreed?

The Ledger has a fixed scope and fee agreed before starting. The Operating Model Review, leadership cover and readiness work are scoped to the decision, responsibilities and involvement required. Duration, fee and exact breadth of the Operating Model Review are agreed before work starts. Ask about scope, exclusions, access, timing and fees before agreeing an engagement.

Does a review certify that we are secure or compliant?

No. The Ledger is a board-level review of the agreed evidence. It is not a penetration test, code audit, exhaustive inventory or legal opinion. Findings should distinguish what the evidence supports from what still needs specialist validation.

Who does the work, and what should I share?

You work directly with Michael Kennedy. Start with the business situation and decision; do not send confidential records in an initial enquiry. Read about information handling, AI use and scope →

Can I see an example without sharing my information?

Yes. The illustrative Ledger board pack is freely readable on this site. Every organisation, figure and finding in it is fictional.

A direct conversation

What is the decision on your desk?

Use a 30-minute conversation with Michael to discuss the situation, the decision or leadership gap, and which form of help may fit.

Book a 30-minute call (Google Calendar, new tab)

Prefer email, or cannot use the calendar?

michael@kennedyadvisory.co

Tell me whether you need leadership cover, a broad technology diagnosis, an operating model review, buyer assurance or vendor readiness. Information handling & scope →

01 / Before

Bring the business question, any deadline and who needs to be involved. Keep confidential material back.

02 / Discuss

Clarify the issue, the role you need and whether leadership cover, a Ledger, an operating model review or readiness work is relevant.

03 / If there is a fit

Define the scope, responsibilities, access, timing and fee before deciding whether to proceed.