AI Sales

I still remember the worst discovery call of my career. I was twenty minutes into what I thought was a brilliant interrogation of a CFO at a growing tech company, rattling off question after question from my carefully prepared list. Budget? Check. Authority? Check. Need? Check. Timeline? Check. I was hitting every qualification box, feeling…

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I distinctly remember a meeting when our sales and marketing teams brainstormed how to grow the business: “We need more leads,” echoed the sales team. “No, we don’t. We need to learn to close better,” said the CMO. “Wait, what’s the actual plan?” said the confused voice in my head. Everyone was brewing with ideas…

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Purchase order numbers. I wonder how many invoices I’ve added PO numbers to in my years as a freelance business reporter. That number may be in the thousands. I’ve seen just as many POs as an online shopper. And, I’ve benefited. Having the correct PO number on my invoice means I get paid a lot…

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I still remember the first time I tried to “build a funnel.” I had just joined a new company, and I wanted to prove myself. I mapped out buyer personas, stacked automation tools, drafted clever messaging sequences, and organized a color-coded CRM that looked like a sales manager’s dream. It was clean, sharp, and complete.…

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Most reps aren’t prepared to sell to C-level executives. Here’s my honest take: Most salespeople are overprepared for objections and underprepared for business conversations. They rehearse demos instead of researching pressure points. They come armed with product knowledge, but not enough market insight. And they try to impress executives when they should be enabling decisions.…

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Last year, I hit a wall trying to scale sales as a solo consultant. I was doing strategy calls, sending follow-ups, chasing proposals — basically playing rep, manager, and ops lead all at once. Hiring wasn’t an option, and most tools I tried just added dashboards, not real help. So I started experimenting with AI…

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I still remember the first time I froze on a sales call. I had no script, no structure. I just had a vague idea of what I was selling and a whole lot of nerves. The executive on the other end waited in silence after my clumsy pitch, and all I could think was, “I’m…

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Insurance gives you an extra layer of coverage when life throws an emergency your way — whether that be a run to the doctor, the mechanic, or the dentist. If you own a business, you can tap into that extra protection with a business owner’s policy. In my years reporting on business and finance, I’ve…

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