Practical, opinionated writing on technology strategy, digital transformation, and the decisions that define how SMBs grow.
Most growing SMBs have IT. Few have anyone deciding what IT is for. The fractional CIO role exists to fill that gap — and most leaders only recognize the vacancy after it has already cost them.
Read →KPMG's 2024 survey of Canadian SMB leaders found that 72 percent reported being attacked by cybercriminals in the past year, up from 63 percent the year before. IBM reports that the average cost of a data breach in Canada reached CA$6.98 million in 2025. A global Mastercard survey of small and medium-sized enterprises found that nearly one in five businesses that suffered a cyberattack then filed for bankruptcy or closed. These are not enterprise numbers describing enterprise problems. They are SMB numbers describing the businesses that believe they are below the threshold of interest. The gap between that belief and the data it contradicts is where most of the exposure lives.
Read →Most SMB technology decisions feel reasonable in the moment and expensive in hindsight. Not because the tools were wrong. Because the problem was never named precisely enough to know what a good outcome would look like. The businesses gaining durable advantage from technology - AI included - are not the ones that adopted earliest. They are the ones that adopted with intent and precision.
Read →Your team is already using AI. You did not authorize it. No one owns what it produces. That is not a future risk. That is the current state of most SMB operations. Every governance model we built for technology was designed for bounded tools. A CRM manages customer data. An ERP runs operations. Each has a defined scope, a clear owner, a measurable outcome. AI has none of those things.
Read →If a semi-technical person can produce a coherent multi-site platform in eight days, the reference points for development timelines, costs, and complexity have shifted. Clients will know this, even when they cannot articulate it precisely. The project that once justified six months and six figures will face a different set of questions.
Read →SMB leaders tend to treat risk as an afterthought, what remains after cost has been managed and growth has been planned. That framing is wrong. Risk in a technology-dependent business is structural. It accumulates in the same way complexity does: through decisions that solved local problems without anyone asking what they left exposed. By the time the business is too big to wing it, the exposure is already embedded.
Read →When customer relationships live in people’s heads rather than in systems, the business is one resignation away from losing its pipeline.
Read →ERP becomes appropriate when core processes are stable enough to standardize without constant exception-handling, when leadership agrees on how revenue, cost, and margin should be defined and measured, when decision rights are clear enough that the system can enforce them, and when growth complexity exceeds what informal control can safely manage.
Read →Outsourced IT can keep systems running. Vendors can demonstrate features. Advisors can recommend platforms. But only leadership can decide how the business is meant to operate. That decision shapes every tool selection, every integration priority, every trade-off between speed and sustainability.
Read →Most SMB "technology failures" aren't caused by bad software. They happen because leaders buy a system expecting it to simply work, then discover, mid-implementation, that the assumption was conditional.
Read →The most dangerous technology decisions don’t fail early. They fail after you’ve built around them.
Read →This is for SMB owners and executives who never planned to “own” technology, yet find themselves approving budgets, resolving escalations, and absorbing the consequences of decisions that seemed reasonable at the time.
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