The Human Side of Go-To-Market AI Can't Replace | GTM Crossroads Ep #8

GTM Crossroads Podcast Ep #08: The Human Side of Go-To-Market AI Can't Replace

In the eighth episode of GTM Crossroads, RevPartners CEO Brendan Tolleson sits down with OutboundSync Founder Harris Kenny, and Octave Co-founder and CEO Zach Vidibor to discuss how go-to-market strategy, pricing models, and product adoption are evolving in an AI-driven world.

They also touch on the tension between automation and human connection, and why trust, relationships, and positioning still matter most.

Check it out! 👇

5 Minute Rundown:

GTM Still Needs Humans

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Zach: "You can’t rip out the heart and soul of your go-to-market and replace it with AI... it's not a panacea in and of itself. It’s an engine, you gotta put a car around it."

As go-to-market (GTM) strategies become more automated and AI-driven, it’s easy to believe technology alone can win deals. GTM still hinges on trust, relationships, and real human connection. Tools help, but they’re just that: tools. The heart of go-to-market is still people selling to people. Ignore that, and your strategy will feel robotic, disconnected, and ineffective.

Events Matter More Than Ever

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Harris: "All this like AI kind of stuff... I think it's like being face to face is pretty important."

Despite the AI hype and shift to virtual everything, live events still carry unmatched weight. MicroConf is a good reminder that in-person conversations spark deeper thinking, create unexpected insights, and drive real alignment on marketing, pricing, and positioning. With Southbound on the horizon, the message is clear: real conversations still move the needle more than any algorithm.

GTM Is Not a Lab Experiment

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Zach: "People think go to market is some riddle you can solve in a laboratory... it’s different at each company. There’s trust involved. There are relationships."

Go-to-market isn’t a science fair project. Treating it like a clean formula leads teams down the wrong path. Success isn’t about reverse-engineering a perfect playbook, but rather adapting to your market, your people, and your context. It’s unpredictable and often messy, built on trust and iteration. The idea that GTM is something you can blueprint and automate from day one is false.

Pricing is Math + Strategy

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Harris: "Sometimes I feel like... is it because my pricing is dumb? Like if I had better pricing, could I solve these problems for people who want me to solve them?"

Pricing decisions shape who adopts your product, how fast you grow, and what kind of customers you attract. It’s not about picking the “right” number, it’s about finding a structure that reflects how people actually want to buy. Especially as new GTM motions like PLG and partner-led emerge, pricing has to flex with how your product is discovered, tested, and expanded.

The Real Challenge Today Is Go-to-Market, Not Product

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Zach: "There's a lot more belief in like, you'll figure out the tech... but can you market it? Can you price it effectively? Can you package it effectively?"

Building products is getting easier. Between AI, templates, and toolkits, the barrier to launching something new is lower than ever. What’s harder now, and more critical, is go-to-market execution. Knowing your ideal customer, crafting the right message, and structuring pricing that makes sense. The skill gap here is what separates momentum from stall-outs.

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