Isaac Chiles has been on both sides of the enterprise sales table — first as a customer, now as a Sales Executive — and he’s learned a lot along the way about what works and what doesn't when it comes to driving business transformation. With nearly a decade in AI-powered workflows, solution consulting, and sales, Isaac’s career has been about finding the sweet spot between technology and real-world business impact. He’s grown territories from 10x, created workshops, been a featured speaker, and built demos that actually help people understand how solutions work in the real world. And he founded eduSwipe, a digital publishing platform that brought authors onto a new business model, shaking up the traditional publishing industry. Isaac believes that anything we spend much of our lives doing is worth doing well, and that learning is always a two-way street. While he’s happy to share what he’s learned from his journey in solution consulting and sales, he’s just as eager to learn from others. Sharing ideas isn’t about lecturing—it’s about creating conversations where everyone can grow, improve, and get better at what they do, together.
Process
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Oct 4, 2022
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4 min read
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The human side of enterprise AI adoption. The capability is real, and it gets cheaper every month. Most organizations still aren't getting value from it. The gap between those two facts is what this newsletter is about. I'm working it out in the open — three years buying enterprise software, seven years selling it, and a decade watching what platforms actually do to the people who have to use them. Every edition is what I'm currently thinking, including the parts I haven't finished thinking. Essays every other week. Field notes in between. For the people accountable for whether any of this actually lands.