AI and the Humanity of Sales

Felicia Shakiba asked me on The CPO Playbook to go back to the exact moment I realized AI was going to change sales for good. It wasn't experimenting with ChatGPT as a party trick in late 2022 — it was a few months later, when I sent a tool a draft of my sales kickoff keynote and it started proactively telling stories about me that I hadn't written down anywhere, pulled from podcasts and articles it had read. It was maybe 80% right, but that was still a huge amount of time back.

I started my career as employee number 26 at a dot-com that briefly became the world's largest tech IPO before Google took that title away, so I've watched one full hype cycle collapse and rebuild already. That's part of why I compare AI today to the early internet: people worried the .com era would put call center agents out of work booking airline tickets, and instead travelers just started flying 300% more, with those same agents doing more of the human parts of the job. I think AI in sales plays out the same way — it takes data prep and account research off a seller's plate so there's more time for the empathy and trust-building AI still can't fake.

That only works with real guardrails. I mentioned Tennessee's 'Elvis Act,' a real law aimed at stopping AI from convincingly simulating someone's voice or likeness, because just because a tool can sound like your CEO doesn't mean it should be allowed to. My advice for any revenue leader starting this work: begin with small, low-stakes pilots that build people's trust in the tool before you ever let it act or speak on your behalf, and keep a human reviewing the output the whole way through.