By Stephen Taylor · Stephen Taylor Advisory · Managing Teams The hardest part of managing a global product team isn’t the time zones. Time zones are a scheduling problem. You solve them with calendar discipline and asynchronous infrastructure. What you cannot solve with a scheduling tool is the more fundamental challenge underneath: the fact that the people on your team do not just live in different places. They have been shaped by different cultures, different professi

Agentic AI systems that take autonomous action are arriving fast in financial services. The product and governance questions they raise are ones most regulated companies are not ready for. Here is what defensible looks like.

In regulated markets, the way you sell is as scrutinized as what you sell. Four GTM levers that move enterprise buyers in financial services, from 150% of quota experience

By Stephen Taylor · Stephen Taylor Advisory · Product Strategy Every regulated SaaS company faces this decision at some point. Usually more than once. Build the capability internally. Acquire a company or technology that has it. Form a partnership or reseller arrangement. All three paths are defensible in the right circumstances. All three are expensive in the wrong ones. What I have observed, having led three technology acquisitions across two organizations and lived t

By Stephen Taylor · Stephen Taylor Advisory · Culture & Teams Culture is not an empty concept. It is not a team offsite, a set of operating principles, or a paragraph in an employee handbook. Culture is what your team does when no one is watching, when the deadline is slipping, when the regulator calls, when a critical defect surfaces the night before a major client goes live. In regulated environments, that definition is not abstract. It is testable in real time. A pro

By Stephen Taylor · Stephen Taylor Advisory · Product Management The first question most incoming product leaders ask when they take a new role is some version of this: “What does the roadmap look like?” It is the wrong question. Not because the roadmap does not matter because quite clearly it does. But the roadmap is a downstream artifact. Asking about it first is like a new head chef asking to see next week’s menu before understanding anything about the kitchen, the s

By Stephen Taylor · Stephen Taylor Advisory · AI Transformation There is a question that a regulator will ask your Chief Product Officer that most AI strategies cannot answer. It was a question that was asked of me in a DC office a few years back. It is not a technical question. It is not about model accuracy or training data. It is this: If this AI system makes a decision that harms a customer, a case, or a compliance outcome — can you explain exactly why it made that