The Right and Wrong Way to Use AI Agents in Customer Service with Jason Maynard, CTO of Zendesk

The Right and Wrong Way to Use AI Agents in Customer Service with Jason Maynard, CTO of Zendesk

The Right and Wrong Way to Use AI Agents in Customer Service with Jason Maynard, CTO of Zendesk

0:00/1:34

Also on

Also on

Jason Maynard, APAC CTO at Zendesk, joins Georgie Healy for a conversation that cuts through the AI automation hype and gets to what is actually happening on the front lines of customer service.

Jason shares the framework every business needs right now for deciding where automation genuinely helps customers and where it quietly destroys trust. He introduces the dolphin problem, the counterintuitive reason why the brands that listen hardest to complaints end up winning the most. And he explains why, despite everything you are hearing about AI replacing jobs, customer service job postings in the United States went up 10% in 2025.

They also get into digital snap and how to design your way out of it, why your AI agent is really just an extension of your brand identity, a brand new role emerging inside service organisations that looks a lot like what happened to marketing in the early 2000s, and three rapid fire scenarios that reveal exactly when you need a human and when you do not.

This is one of the most grounded and practical conversations we have had on the show about what AI in customer service actually looks like when it is done well.

This Episode Is Brought To You By Our Partners

Click our partners below to see their unique offers

More Episodes You Might Like

Let's talk

Turn podcasting into pipeline

We help founders, funds and operators build trust, authority and deal flow with a show tailored to their market.

Win better deals and stay top‑of‑mind with founders.

Close more deals and build a category you own.

Reach founders and operators with a show they trust.

Day One® exists to help founders and startup operators make better business decisions more often

Subscribe for helpful content from other successful founders, operators and investors

Join 755 other founders & investors receiving our emails. They're cool, are you? :)

* Regrettably, mel@canva.com is not on our list… yet.

Day One® is a registered trademark of W2D1 Media Pty Ltd. All rights reserved. © 2026 W2D1 Media Pty Ltd.

Day One® exists to help founders and startup operators make better business decisions more often

Subscribe for helpful content from other successful founders, operators and investors

Join 755 other founders & investors receiving our emails. They're cool, are you? :)

* Regrettably, mel@canva.com is not on our list… yet.

Day One® is a registered trademark of W2D1 Media Pty Ltd. All rights reserved. © 2026 W2D1 Media Pty Ltd.