Jesse runs global sales development at Tipalti, a company that automates global payable operations. His org has 100+ SDR’s, 17 SDR Managers, and 4 SDR Directors across 7 cities.

Jesse is a history enthusiast and early adopter of AI, who also approaches tech adoption with two feet grounded in reality. It’s refreshing.

He sat down with Luke from Origami to explore old-school sales fundamentals and cutting-edge AI tools. 

I always tell people we've been dealing with this for hundreds of years. 

When Samuel Morse invented the telegraph because his wife died while he was away and no one could reach him, it put the Pony Express out of business. Everyone freaked out about technology replacing jobs. 

But the telegraph eventually gave us the telephone, which gave us the internet, which gave us AI. We're in year one of when the telegraph was invented. Everyone's like, "Oh my God, we're all going to be out of a job soon." 

But human beings continue to move on. They continue to have desires and problems that need to be solved. And there will be jobs to solve those problems.

I'm one of the biggest embracers of AI around here, but I worry about people getting overly reliant on it. 

I see folks doing account research in ChatGPT, asking it to craft personalized messages, then just taking it and going with it. 

There's an element of critical thinking that's lacking. 

When I started in sales, we didn't have automation. Every email was manual, so you had to use critical thinking. You had to think about who you're reaching out to, what you're saying, how it'll resonate.

I'm not expecting people to manually type every email, but when you're forced to, it makes you think differently than just copy-paste.

People are going to crave human connection more than ever. I think there's going to be a big uptick in events and trade shows.

There was a drop-off with COVID, but I think people will start going more because they're sick of interacting with AI. They want to shake someone's hand.

So when buying a tool, my philosophy is this - automate all the mundane stuff, but invest heavily in that human connection piece.

We recently went through a renewal with an AI tool and got pushback on ROI. Finance wants to see "spend $100, make $1000," but there are other factors. 

I don't have a clear number, but there's an element of stability. This AI tool gives us 100 predictable meetings per month regardless of turnover or new hire ramp-up. 

How do you value that stability? 

If I can have 100 meetings from AI and 300 from SDRs, that 100 is steady Eddie. It doesn't matter if we have hiring challenges. 

That's hard to articulate to finance, but the predictability has real business value that traditional ROI calculations miss.

That’s it for this week!

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Find more Modern GTM interviews here.

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And connect with Luke + Eric, if you feel so inclined.

‘Til next time!