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When people ask me how to get into transformation work, I usually have to start by admitting that I did not get into it on purpose.
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I have spent most of my career telling people that if you do the work right, the outcomes follow, and for a long time I believed that was the whole story.
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I've now worked inside very nearly every funding model there is, and they each leave a mark on how you think.
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I have watched the same thing happen enough times now that I have stopped being surprised by it, which is its own kind of sad.
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For most of my career, the holy grail in data was real time, and everyone in the field chased it.
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There is a statistic that gets quoted in almost every conversation about digital transformation, the one that says seventy percent of them fail, and I have heard it repeated so many times, in so many rooms, that it has stopped functioning as a fact and st…
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When I step into a new role, the first thing I do is go wide, fast, and the document I reach for before almost anything else is the org chart, because that single page tells me more about how a company actually behaves than any deck or strategy memo ever…
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Rainfall cleared the App Store today, which is a nice sentence to be able to write, but the approval was never really the thing I was testing.
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I have been building my own things lately, partly because I have always wanted to, and partly because anything I build might one day be worth something to someone else.
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A couple of years ago I was on the buying side of this exact problem, and I want to start there, because it is the part I think about most now that the situation has reversed itself on me.
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When a company decides that its sales force could be doing better, the proposed fix is almost always the same thing, and it's almost always delivered with total confidence.
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When I describe the data problem we inherited at Southern Glazer's, people tend to assume I'm exaggerating it for effect, and I'm not.
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When I describe what we built at Southern Glazer's, the line that lands hardest with people outside the beverage-alcohol world is the one that sounds least likely on its face.
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The integration of AI into enterprise engineering is genuinely reshaping how organizations manage their product development teams.
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At a company I worked with earlier in my career, someone made an observation in a meeting that I have genuinely never been able to forget.
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The trouble with projects, the thing I kept running into for years before I could name it cleanly, is that they end, and the uncomfortable truth is that not everything should.
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When Proof launched, our sales team was fairly convinced it was there to replace them, and the honest thing to say is that they were not wrong to worry.
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There is a warehouse worker I keep thinking about, long after the project that introduced me to his story has ended.
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As we navigate the complexity of engineering, product development, and digital transformation, it is easy to find ourselves trapped in a cycle of relentless problem-solving.
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Nearly every business book I have ever read puts a revenue goal squarely inside the vision, and I have come to do the opposite.