CC

Chris Cunningham

Things Chris Says on Podcasts

Where to Find Them

Chris Cunningham has been a guest on The Marketing Millennials (2 times) , Founder's Story , The Dave Gerhardt Show (from Exit Five) , Do This, NOT That: Marketing Tips with Jay Schwedelson , The Rich Somers Report and Ahrefs Podcast .

Recently: “How To Win in B2B Social in 2026 with Chris Cunningham, Founding Member at ClickUp” on The Marketing Millennials (October 2026); “SPECIAL GUEST!! ClickUp's Co-Founder Chris Cunningham đź’¸ The $1,000 Content Hack Big Brands Miss | Ep. 532” on Do This, NOT That: Marketing Tips with Jay Schwedelson (July 2026); “How ClickUp Built a B2B Social Machine with Chris Cunningham from ClickUp” on The Dave Gerhardt Show (from Exit Five) (April 2026); “How To Win in B2B Social in 2026 with Chris Cunningham, Founding Member at ClickUp | Ep. 378” on The Marketing Millennials (December 2025); “Unpacking the Social Media Playbook of a $4B brand | Chris Cunningham (ClickUp)” on Ahrefs Podcast (July 2025); “The Path to 200 Million Impressions: Chris Cunningham’s Secrets to ClickUp’s B2B Success | S2 Ep. 151” on Founder's Story (November 2024).

What They Said

Asked how he thinks about AI content for 2026, ClickUp's Cunningham says he uses AI for ideas and streamlining but not for scripts or whole strategies, arguing audiences currently reward real human creators.

The Marketing Millennials · 2026-10-30 Permalink → Listen →
The Marketing Millennials Around 34:31 into the episode
Chris Cunningham

Doesn't mean they cared about it.

Daniel Murray

…impressions, CAC payback goes down, cost acquired, customer goes down, people know about click up more. All these metrics start going in the right direction. That's how you sell it. I think that's perfect. I wanted to ask you too, how are you thinking about AI content using AI and social in 2026?

Chris Cunningham

You know, I don't probably have the hottest take on here. I'm still in the camp of, I love AI. I use AI all the time. I don't think you should fully automate your content with AI. Like, I'm not the believer in that. I don't think it writes the best content. I don't use it for my scripts. I might use it for ideas here and there, but everyone's saying, oh, AI is just going to make every video. Okay. I don't see it yet. Because I still think right now people want creators. They want like genuine human. If anything, I've seen that requested more. Like they still, they'd rather see a lot of AI videos don't perform, right? Because people, they know it's AI and they want to keep scrolling. However, I do think there's a lot of good things you can do with AI. I've created an AI meme page. I think that's pretty good. I think you can still make some funny quick memes, images, videos without putting too much work into it and have some success with some thought. So I do believe in those. I do believe in still creating, like I posted an AI video the other day for clickup. I still believe in like making AI videos, but I don't believe making your whole strategy. And I don't believe handing…

Daniel Murray

Yeah, I think that's the best way to put it right now. Understand why it works, how it works, how to do it. But I do, I'm in the camp also, is there's some human things that AI can't replicate and this humor that hasn't been told yet that human, only humans could do this scripts. I feel AI doesn't…

Chris Cunningham

Exactly. That's a good way of saying it.

Daniel Murray

I want to ask you a question that I ask everybody in this podcast: what is a marketing hill you would die on?

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.