158 Sales Tools. One Honest Assessment

Summer Poletti asked me on Revenue Remix whether I ever sleep, given the CRO-of-the-year title, five private equity exits, and a food sanitation license I renew every four years to help serve 12,000 homeless meals a year in Chicago. The honest answer is that I get excited about something and go deep — sales, nonprofits, or, as it turns out, researching 158 different AI sales tools for a new book.

I told her about the Chicago Bell Garden, a joke restaurant I invented on Facebook during the pandemic for my tiny rooftop grill. A vegan burger company saw a photo with three likes, assumed I was a real bistro using a competitor's product, and started shipping me industrial-sized samples of kimchi, steak rub, and vegan cookies to win my business. Somebody's AI bot had made a real spending decision based on a joke it couldn't recognize as a joke, which is exactly the risk I now spend most of my time warning revenue leaders about.

Sequoia called it the $200 billion question two years ago; now it's the $600 billion question, because that's roughly what we've collectively spent chasing AI without much proof of return. My answer, and the core argument of The AI Handbook for Sales Professionals, is that AI should be treated as the new lowest-cost resource: the tool you hand your data prep and account research to, the same way you'd hand it to an intern, so sellers get their time back for the parts of the job only a person can do.

That only works with real oversight. The book lays out a maturity model that starts with small, low-stakes pilots before AI ever touches a customer directly, and every deployment stays human-led and human-reviewed, because the tools still get things wrong — sometimes in ways that cost you a case of kimchi, and sometimes in ways that cost a lot more.