Every salesperson on LinkedIn was President’s Club. Every resume shows quotas exceeded, records broken, number one on the team. But in a thirty-year career, nobody was at the top for thirty years in a row.
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Some habits never leave you. They simply evolve. For me, puzzling has always been one of them—a quiet, obsessive activity that pulls me in completely and refuses to let go until the last piece clicks into place.
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The myth of the founder-as-superseller has done real damage to early-stage companies. We have romanticized the image of the charismatic CEO who can close any room, and as a result we have pressured technical, product-obsessed, or operationally minded founders into roles they are temperamentally and skill-wise unsuited for.
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Reading was not assigned—it was inevitable. Books were not just a pastime; they were my primary form of entertainment, my travel to a different place and time.
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In last week’s CEO Masterclass, I laid out the common reasons why fractional executive engagements go sideways. Then one of the CEOs in the room did something that made the lesson land harder than any slide could: he squarely confirmed it.
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Fractional executives have always sold one thing above all: pattern recognition compressed into fewer hours. Artificial intelligence is now rewriting what those hours look like — for GTM leaders (fCMOs, fCROs), fCFOs, fCOOs, and fCTOs alike.
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The problem isn't product complexity. It isn't market conservatism. And it isn't price; sports technology is full of non-negotiable procurement decisions made at prices nobody expected the buyer to accept. The problem is translation.
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This one begins on a cold January Sunday, somewhere far enough from home to feel like an expedition, with frozen ground under our feet and one simple promise that kept us moving: there would be a fire, and we would grill sausages.
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Some people have photo albums that tell the story of their childhood. I had a wooden chest full of broken electronics—my personal monument to experimentation, triumph, and the occasional small explosion. Oddly enough, that chest has shaped how I lead a business far more than any textbook ever has.
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In the early life of a startup, few challenges are as misunderstood—and as costly—as building the first sales engine. Founders often assume that hiring a few salespeople will automatically translate into predictable revenue.
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