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Strategies, advice and opinions helping to define and develop the role of IT leaders and their staffs.

The Greatest CIO Interview of All Time

Most interesting CIO





He fixed a catastrophic mainframe failure with the pointy end of a rat-tail comb.

He refereed an arm-wrestling contest between Bill Gates and Steve Jobs.

He was a moustache double for Tom Selleck during season four of Magnum PI.

He correctly texted the Declaration of Independence while running with the bulls at Pamplona.

He is… “The Most Interesting CIO in the World”.

It is doubtful that there is anyone in IT today who is not familiar with the exploits, accomplishments, intrigues and affaires of The Most Interesting CIO in the World. His brash – some would say swashbuckling – approach to IT management, as technology head of three of the world’s leading organizations, is the stuff of legend.

But until now, this very public figure has proved devilishly difficult to pin down for an interview. Happily, that ends today with the publication of this conversation, which I recorded with my famous seatmate during a flight to Rio, where he was delivering a paper on “Superstring Theories and their Impact on IT Management”.

Me: You are amazingly knowledgeable on a host of different subjects. You could have been anything you wanted. What made you decide to become a CIO?

TMICIOITW: It was not easy, my friend. After my return from the New Guinea rainforest, where I spent nine weeks in a 60-meter high tree house as a guest of the lost Korowai tribe, I decided that my life was lacking the kind of challenge and exhilaration to be found in only a few professions: black mamba wrangler, Formula One driver, tornado chaser. But after much consideration, the choice was clear. No profession held more excitement for me than that of CIO – these digital high-wire artists who, it could be argued, control the fate of corporations, of nations, of humanity itself.

Me: It has been widely reported that the world was spared from the global Y2K computer meltdown because of a hundred lines of code you wrote on the back of a napkin while waiting for a hamburger at Solly’s Grille in Milwaukee. Is there any truth to that?

TMICIOITW: Like many things written about me in the press, the story is inaccurate. It was a bacon double cheeseburger.

Me: You have been linked with some of the most beautiful women of our time: Angelina, Scarlett, Jennifer, Mila, to name a few. Why do you think that you, in particular, and CIOs in general are so sought after by such women.

TMICIOITW: My fantastico moustaches notwithstanding, beautiful women are naturally attracted to men of great power, gravitas and sexual magnetism – traits common to all CIOs, men and women alike. We are a rare breed, my friend.

Me: Some say that you invented the Internet two years before Al Gore. Is that correct?

TMICIOITW: Al Gore is a great man. Perhaps not the fastest off the mark on some things, but a great man, none the less. That is all I will say on the matter.

Me: You are said to be working on a personal digital device that will be more popular than tablets, cell phones and GPSs combined. What can you tell us about that device?

TMICIOITW: I do not like talking about things before they are a reality. But I will offer you two words, my friend – make of them what you will. Electronic hamster.

Me: According to the latest rumours, you have set your sights on creating Canada’s answer to “Burning Man”, the annual temporary community built in the Black Rock Desert, dedicated to radical self-expression. What can you tell us about that project?

TMICIOITW: In this case, the rumours are indeed true. I am in the early stages of organizing “Freezing Man”, to be held every February on the Barnes Ice Cap on Baffin Island. This event will be dedicated to radical self-preservation. Like its counterpart in Nevada, it will be clothing optional.

Me: That sounds pretty extreme.

TMICIOITW: Only for those who are unprepared. As every CIO knows, preparation is everything. I have already begun immersing myself in a bath of ice cubes for one hour every night.

Me: You have been CIO of the world’s largest bank, the world’s biggest entertainment conglomerate, and the world’s most successful agribusiness. You have helmed IT teams larger than the population of Iceland and Tonga combined. Is there anything left for you to do as a CIO?

TMICIOITW : Never fear, my friend, there are plenty of things to do. Only last week I was lining up an eagle putt on the 13th green at Augusta, when my partner, Barack, said more or less the same thing to me. I reminded him of the words of another famous man, the great tenor Luciano Pavarotti, who once lamented, “You just can’t buy Beatle boots no more.” As my double-breaking 30-footer found the centre of the cup, I said to him, “The challenges for the CIO are endless, Barack. With exceptional IT management, we can make a world in which we will want for nothing – not even Beatle boots.”

Me: I would be remiss if I did not ask you about your predilection for a certain brand of Mexican liverwurst, which seems to be ever present when you are caught by the cameras. Some say it is made of horse meat.

TMICIOITW: I don’t always eat liverwurst, but when I do I prefer Dos Equus.

With a wry smile, he added, Stay hungry, my friend.

He then reclined his seat and soon began to snore gently.

Past Attendees

ADP - VP Architecture & Infrastructure

AESO - VP, Information Technology

Agnico Eagle Mines - VP, IT

Agrium - Global Mgr., IT Security

Agrium - Senior Director IT Shared Services

Aimia - SVP & Global CIO

Ainsworth Engineered - Director IT

Air Canada Vacations - Director IT

Alberta Energy Regulator - Director, Office of the CIO

Anthem Properties - VP IS

AON Risk Solutions Canada - Head of IT

Avison Young - VP Global Enterprise Architecture & Integration

Aviva Canada - VP, Architecture & Strategy

Bank of America Merrill Lynch - CTO

BC Ferry Services - VP & CIO

Bell Business Markets - Director, Strategy & Planning

Bell Canada - National Director, Digital Transformation

Bellatrix Exploration - Director, Information Technology

Bentall Kennedy - VP IT


BFL CANADA - Director, Cybersecurity & IT Risk Management

Black Press - CTO

BlackBerry - VP Corporate IT

BMO Financial Group - Director, Technology & Operations Transformation

BMO Financial Group - Head of Services Delivery

Bombardier Aerospace - CISO

Bonavista Petroleum - Head of IT

Borden Ladner Gervais LLP - Global CIO

Bow Valley College - Director, IT Services

Bridgewater Bank - Head of IT

BuildDirect - VP IT

Bulk Barn - Head, IT

Burnco - CIO

Caisse de Depot et Placement du Quebec - VP, IT Planning, Architecture, Governance, Operations

Calfrac Well Services - Head of IT

Canada Goose - CTO

Canada Live - VP of Technology

Canada Mortgage and Housing - VP, Information & Technology

Canada Protection Plan - Head of IT

Canadian Depository for Securities - CIO

Canadian Direct Insurance - CTO

Canadian Payments Association - VP & CIO

Canucks Sports - Head of IT

Capgemini - Service Delivery Director


Cardel Homes - VP MIS

Cargojet - CIO

CBI Health Group - CIO

CCS Corp. - VP IT

CDSPI - Board Director

Centerra Gold - Director IT & Comm

CI Global Asset Management - VP of Enterprise Infrastructure $amp; Operations

CIBC - Senior Director, Infrastructure Planning & Engineering

CIBC - SVP & CIO, Retail and Business Banking Technology

CIBC Mellon - AVP, Enterprise Architecture

CIBC Mellon - SVP & CIO

Cineplex Entertainment - CTO

City of Brampton - Senior Manager, IT Architecture & Planning

City of Richmond Hill - CIO

City of Toronto - Director of Strategic Planning & Architecture

CN Rail Service - Chief Information Security Officer

Coast Capital Savings - VP Technology

Colliers - Head of Technology & Data

Concordia University - AVP & CIO

Crescent Point Energy - Head of IT

Dairy Farmers of Ontario - Head of IT and Administration

Dale Parizeau Morris Mackenzie - VP, IT

Davies Ward Phillips & Vineberg LLP - Director, Information Technology

DealerTrack Canada - Director, Technology

Defence Construction Canada - Corporate Manager, IT

Deloitte - Director, Risk Advisory

Dentons - Canada CIO

Devon Energy - Director, Integrated Business Services

Direct Cash - VP IT & Security

Dynamic Tire Corp - CIO

D+H Partnership - VP, Head of Canadian Mortgage Technology

eHealth - EVP, Technology

eHealth Ontario - VP, IT Systems & Services

Encana - Director, InfoSec

Enbridge Inc. - VP, Technology and Information Services

Enerflex - CIO

Enerplus - VP. IS


Equitable Bank - CIO

Equitable Bank - CISO

Equity Financial Trust - VP, IT

Essential Energy Services - Director, IT

Expedia Cruise Ship Centers - VP IS

FGL Sports - VP, Information Technology

Finastra - SVP, Head Technology Managed Services

Fix Auto Canada - COO & SVP - CIO

Freedom Mobile - Head, Customer Applications, Experience, & Strategy

FT Services - CIO

FundServ - CIO

Genus Capital Management - CTO

Genworth Financial Inc. - VP IT

Geotab - Board Member

Golder Associates - CTO

Gran Tierra Energy - Director IT

Grant Thornton LLP - CIO

Grand River Hospital - Director, Data Governance & Analytics

Greenwin Inc - VP, Information Technology

Groupe Dynamite - Director, IT

GSK Canada - IT Director

GTAA - Acting CIO

H&R Block Canada - VP IT

Haventree Bank - VP, Technology

Hewitt Equipment Ltd. - VP & CIO

Hitachi Vantara - GVP & Global CTO

Home Trust Company - CIO

Home Trust Company - CTO

Home Trust Company - VP & CISO

Horizon North Logistics - CIO

HSB Canada - VP IT

IBM Canada - Associate Partner, Payments Industry

Indigo Books and Music - CIO

Interac Corp - Director, Platform Engineering

ivari - SVP & CIO

JP Morgan Chase Canada - Executive Director, Information Risk Management

Keyera Energy - Director, Information Technology

KFC Canada - CTO

KnowledgeOne - CIO

LaFarge Canada - Director, IT

Landmark Cinemas Canada - VP, IT


LCBO - Director, Applications Systems


Leisureworld Senior Care Corp - VP IS

Lifeguard Digital Health - Chief Security & Informatics Officer

Loblaw Companies Ltd - Senior Director, Customer Engagement Technology

London Drugs - GM IT

Loto-Quebec - Corporate Director, InfoSec

Magna International Inc - VP & Global Leader, IT (CIO)

Manulife - Global Head of Private Markets & Real Estate Technology

March Networks - VP Professional Services & CIO

MaRS Discovery District - Managing Director, Fintech and Commerce

McCain Foods Limited - Manager InfoSec

McInnis Cement - Director of Information Technology

Medical Pharmacies Group - VP, Information Technology

MEG Energy - Manager, Information Technology Solutions & Services

Metrolinx - EVP & CIO

Minto Group - VP IT

MMM Group - CIO

Montreal Police Service - CIO

Morguard Investments - CIO

Moulding & Millwork - CIO

MullenLowe Group - Global CIO

National Bank of Canada - Information Security Officer

National Capital Commission - Chief, IT infrastructure & Support Services

NHL Players' Association - Head, Security & Technology

Northbridge Financial Corp - CIO

OEC Group Canada - Vice President, Information Technology and Client solutions


Oildex - VP, Architecture & Infrastructure

OPTrust - AVP, Enterprise Data Services

Olympia Financial Group - CIO

OMERS - EVP, Data & Technology


OMERS - SVP, Data & Advanced Analytics

Ontario Pension Board - CTO

Ontario Teachers' Pension Plan - SVP, Product & Delivery

Ontario Trillium Foundation - CIO

Osum Oil Sands Corp - Manager, IS

Ottawa Police Service - CIO

Pacific Western Transportation - CIO

Packers Plus - Global IT Director

Pason Systems - Manager, Digital Communications & Corporate IT

Patient News - CTO

Peel District School Board - CIO

Pengrowth Corp - Director IS

Penn West Exploration - Snr. Manager, IT Operations

Peterson Investment Group - Head of IT

PFB Corp. - CIO

Pizza Pizza - CIO & VP, IT

Precision Drilling - VP, IT

Precision Drilling - Director, IT Infrastructure & Security

PSP Investments - Snr. Director, Internal Audit & Business Infosec

Public Works and Government Services Canada - Director, IT Security Directorate

PwC - Managing Director, Real Estate Technology Advisory

Pythian - CTO

Qantas - Global CIO

Queen's University - Director, Information Technology

RBC Royal Bank - Head of Application Security, Data Protection & Security Consulting

RBC Royal Bank - VP, Technology Platforms & Risk Management

RBC Royal Bank - Global Cybersecurity VP

Regal Lifestyle Communities - CIO

Revera Inc. - CIO

Revera Inc. - Security Architect

Rheem Manufacturing - CISO & Enterprise Architect

Ricoh Canada - VP,IT

RioCan Property Services - VP IT

Roche - Head of IT Americas – Operations

Rogers Communications - SVP, Customer Experience IT


Russel Metals - VP,IS

Salvation Army Canada - Board Director

SCI Group - CIO

Scotiabank - Head, Systems Architecture & Platform Modernization

Scotiabank - VP - International Systems Technology

Scotiabank - Head, System Architecture & Platform Modernization

Scotiabank - Global Head, GBM Compliance & Transformation

Sears Canada - Divisional VP, Information Technology Services

Secure Energy Services - GM, IT

Shaw - Head, Customer Applications, Experience, & Strategy

Shaw Communications - VP, Technology Operations

Shaw Communications - Director, Risk Management

SMART Technologies - Director, IS Corporate Services

Smartcentres - Director IS, IT

SmartOne Solutions - President & CIO

Societe de Transport de Montreal - Division Head - Security and Compliance

Street Capital Financial - CIO

Sun Life Financial - AVP, Data & Business Intelligence Services

Sun Life Financial - VP Application Ops & Services

Sunco Communication - COO

Suncor Energy Inc. - Director, Application Portfolio Optimization, I&PM, Business Services

Symcor - CTO, VP Technology Services

Talisman Energy - SVP IT & Business Services

TD Bank - Enterprise Architect

Teknion - SVP, CIO

TELUS - Chief Security Architect

Tervita Corporation - VP, Information Technology

The Hudsons Bay Company - VP Technology

The Hudson's Bay Company - SVP & CIO

The Source - VP, Information Technology

TMX Group - CISO & Global Head of Infrastructure Services

Toromont Industries - VP & CIO

Toronto District School Board - Chief Technology Officer

Toronto Hospital for Sick Children - Director of Technology

Toronto Parking Authority - CIO

Toronto Police Services - CISO

Toronto Transit Commission (TTC) - Chief Enterprise Architect

Toronto Transit Commission (TTC) - CIO

Toyota Canada - National Manager, IS

Transamerica Life Canada - CIO

Trican Well Services Ltd. - Director, Business Information Systems

Tridel Corporation - CIO

Trillium Health Partners - IT Director, Applications & Clinical Informatics

UFA Cooperative - VP & CIO

University of Calgary - Executive Director, Development Services

University of Ottawa - CIO

University of Ottawa - Senior Director IT Services & Infrastructure

University of Toronto - Director, Centre for Management & Technology

University of Waterloo - Director, Technology Entrepreneurship

Valencia Risk - Managing Director

Vancity - VP Technology & Solutions

Viterra - Director Enterprise Technology

Wawanesa Mutual Insurance Company - Director of Innovation Outpost

World Health - Director IT

Wolseley Canada - CIO & COO

WSIB - Board Director

Yellow Pages Group - Director - Enterprise Data Management

York Region District School Board - CIO

York University - Board Director

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