The Dave Gerhardt Show (from Exit Five)

#347 | ClickUp drives millions of impressions for the company through videos and content for B2B marketers on social, and in this episode Dave sits down with Chris Cunningham, a founding member of the marketing team at ClickUp and the guy who runs social there now, to talk about how they do it. Chris breaks down why 99% of companies are doing social wrong, how ClickUp runs a weekly writers room and shoots 12 to 15 videos every Thursday, and why he tests every video with multiple hooks using Instagram trial reels before it ever hits the main feed. He also gets into how he manages 35 accounts across platforms, how he finds unknown creators with small followings and turns them into writers, and how this has driven real pipeline. Then the conversation shifts to AI and whether doubling down on human creativity might actually be B2B's biggest competitive advantage right now.

Timestamps

(00:00) - - Intro

(04:25) - - Chris's background and why he's been at ClickUp for nearly a decade

(06:21) - - The biggest mistake B2B companies make on social

(08:29) - - The rule of three: make people feel something, teach them, or make them laugh

(09:40) - - Why you should create for two platforms and distribute everywhere

(11:34) - - How ClickUp separates brand, comedy, and product accounts

(13:41) - - How social has driven real pipeline and closed deals

(16:01) - - How Chris interviews ICPs to find content ideas

(20:02) - - How to measure social when attribution is hard

(25:08) - - The weekly production process: writers room, shoot day, and content bank

(32:16) - - Tools and how to manage posting across 35 accounts

(33:50) - - Don't sleep on Facebook Reels

(35:22) - - How to start if you're camera shy and how to find unknown creators

(41:04) - - Where AI fits in and why doubling down on human creativity is the biggest moat

(45:48) - - Why brand is now the biggest competitive advantage in B2B

(47:55) - - Unique content formats worth studying and stealing

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/
***
Brought to you by:
Customer.io - An AI powered customer engagement platform that help marketers turn first-party data into engaging customer experiences across email, SMS, and push. Learn more at customer.io/exitfive.
Consensus - An AI-powered interactive demo platform that lets you put personalized, self-serve demos on your site to turn anonymous researchers into high-intent leads. Learn more at goconsensus.com/exitfive.
Knak - A no-code, campaign creation platform that lets you go from idea to on-brand email and landing pages in minutes, using AI where it actually matters. Learn more at knak.com/exitfive.
Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.

***
Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.
They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.
Visit hatch.fm to learn more

#346 | Dave sits down with Drew Pinta, Director of Growth Data at Ramp, to talk about what it actually looks like to measure marketing when the hardest things to measure are often the ones working hardest. Drew breaks down how Ramp uses incrementality testing and event studies to put real numbers on brand stunts, how they split budget 70/30 between proven channels and experimental bets, and how scanning thousands of Gong calls with AI surfaced attribution insights that contradicted every model they had. He also makes the bull case for why marketers might be better positioned than engineers in the age of AI, and doesn't shy away from the bear case either.

Timestamps

(00:00) - - Intro

(04:25) - - Drew's background: from the Fed to growth data

(07:15) - - Drew's role as a data partner to marketing

(09:51) - - How Ramp's funnel works

(11:34) - - Using AI to scan Gong calls and finding attribution was wrong

(16:15) - - Why measurement should meet the marketing, not the other way around

(27:50) - - The 70/30 budget split

(28:50) - - Ramp's channel maturity framework

(36:36) - - The marketing leader as pilot, data team as instruments

(39:51) - - The bull case: why marketers are better positioned than engineers in the age of AI

(43:36) - - The bear case

(48:36) - - Real AI workflows Ramp's marketing team has built

(53:30) - - How Ramp enabled the team on AI

(56:01) - - Guardrails for AI agents

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/
***
Brought to you by:
Customer.io - An AI powered customer engagement platform that help marketers turn first-party data into engaging customer experiences across email, SMS, and push. Learn more at customer.io/exitfive.
Consensus - An AI-powered interactive demo platform that lets you put personalized, self-serve demos on your site to turn anonymous researchers into high-intent leads. Learn more at goconsensus.com/exitfive.
Knak - A no-code, campaign creation platform that lets you go from idea to on-brand email and landing pages in minutes, using AI where it actually matters. Learn more at knak.com/exitfive.
Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.

***
Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.
They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.
Visit hatch.fm to learn more

#345 | Luke (Head of Growth & Marketing, ElevenLabs), Liz (CMO, Brain Labs), Vicente (Creative Director, Bitly), and Carter (Global Brand Team, UiPath) join this Exit Five Live session to show how they're actually using AI to do creative work. Luke breaks down how his team built a full brand video with one person in one day using voice cloning, image models, and AI video tools. Liz shows the Claude skill her team built so anyone in the org can self-serve on-brand design without going through a designer. Vicente walks through how Bitly cut video production time by two weeks using AI. And Carter shares how he's leading a video initiative that's changing the way a global brand team operates. If you're tired of AI hype and want a look at what people are actually doing, this one's for you.

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/
***
Brought to you by:
Customer.io - An AI powered customer engagement platform that help marketers turn first-party data into engaging customer experiences across email, SMS, and push. Learn more at customer.io/exitfive.
Consensus - An AI-powered interactive demo platform that lets you put personalized, self-serve demos on your site to turn anonymous researchers into high-intent leads. Learn more at goconsensus.com/exitfive.
Knak - A no-code, campaign creation platform that lets you go from idea to on-brand email and landing pages in minutes, using AI where it actually matters. Learn more at knak.com/exitfive.
Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.

***
Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.
They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.
Visit hatch.fm to learn more

#344 | Dave sits down with Katelyn Bourgoin, founder of Unignorable, to talk about the one strategic move most B2B marketers overlook: owning an idea so tied to you that it sounds like an echo coming from anyone else. Katelyn breaks down the six types of ownable ideas, from coined categories to named problems to X vs. Y frameworks, and walks through how to find the central argument your brand should be built on. They also get into why category creation isn't always the answer, what made "conversational marketing" work at Drift, and why ownable ideas matter more now than ever.

Timestamps

(00:00) - - Intro and Dave recaps the Exit Five Marketing Leadership Retreat

(03:27) - - Katelyn introduces the concept of ownable ideas

(07:58) - - Katelyn's background: failed startup, buyer psychology, and finding her niche

(10:45) - - What an ownable idea actually is (and why it's not category creation)

(13:00) - - The 6 types of ownable ideas with examples

(18:39) - - How to find your central argument (the webinar software example)

(21:20) - - Katelyn breaks down Dave's own central argument back to him

(26:48) - - The chocolate covered almond analogy

(28:49) - - How Dave extracted the ownable idea at Drift

(30:12) - - Why the founder has to own marketing (and what to do if they don't)

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/
***
Brought to you by:
Customer.io - An AI powered customer engagement platform that help marketers turn first-party data into engaging customer experiences across email, SMS, and push. Learn more at customer.io/exitfive.
Consensus - An AI-powered interactive demo platform that lets you put personalized, self-serve demos on your site to turn anonymous researchers into high-intent leads. Learn more at goconsensus.com/exitfive.
Knak - A no-code, campaign creation platform that lets you go from idea to on-brand email and landing pages in minutes, using AI where it actually matters. Learn more at knak.com/exitfive.
Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.

***
Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.
They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.
Visit hatch.fm to learn more

#343 | In this session from Drive 2025 titled “Building Pipeline in the Shiny Object Era”, Jen Allen Knuth unpacks why deals stall even when your product is objectively better, how the explosion of shiny tools and AI noise is making it worse, and why most teams are unintentionally fueling the problem with me-centric messaging. Jen shares the two zero-dollar exercises every team should run to quantify how much pipeline they’re losing today, align sales and marketing around the true blocker, and rebuild outbound messaging that creates curiosity.

PS. Want to join us at Drive 2026?
Head over to exitfive.com/drive to grab your ticket. 

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/
***
Brought to you by:
Customer.io - An AI powered customer engagement platform that help marketers turn first-party data into engaging customer experiences across email, SMS, and push. Learn more at customer.io/exitfive.
Consensus - An AI-powered interactive demo platform that lets you put personalized, self-serve demos on your site to turn anonymous researchers into high-intent leads. Learn more at goconsensus.com/exitfive.
Knak - A no-code, campaign creation platform that lets you go from idea to on-brand email and landing pages in minutes, using AI where it actually matters. Learn more at knak.com/exitfive.
Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.

***
Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.
They give you unlimited podcast editing and strategy for your B2B podcast.
Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.
Visit hatch.fm to learn more