Most of my career maps to five recurring situations. Each page covers what the problem looks like from the inside and what I've done about it.
“A major customer just asked for our SOC 2.”
Most companies meet this problem cold: a major customer or prospect suddenly requires SOC 2, ISO 27001, or HIPAA, nobody in-house has done it before, and the clock is contractual. I have been through that full cycle, starting from zero.
More on this →“We’re supposed to have an AI strategy.”
Boards want AI; budgets want returns you can defend. The hard part is measuring honestly, and being straight about where AI will not work in a given business.
More on this →“We’ve outgrown our MSP.”
Growing companies often discover they are paying managed-service prices for break-fix outcomes, with rising costs, slow support, and nobody owning technology strategy. I have rebuilt that situation more than once.
More on this →“We’re buying a company (or being bought).”
Technology risk can quietly reprice a deal, or stall an integration for years. Most diligence checklists miss client dependencies, key-person risk, and the real cost of systems consolidation.
More on this →“Technology is holding back our growth.”
Systems that don’t talk to each other, reporting nobody trusts, projects that never land, and no one senior enough to own the roadmap or challenge vendors. Most growing companies hit this wall eventually; untangling it has been the core of my career.
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