#312 | Jess Lytle (Head of Marketing at Exit Five) hosts a roundtable with a group of email experts on what’s actually working in email, SMS, and in-app messaging right now. They dig into AI’s impact on the inbox, how to sound human when everyone’s using the same tools, and why relevance beats volume. The group also breaks down how to personalize without being creepy, what to do with “lurkers” who never click but still convert, and how to build messaging that survives the AI slop era. It’s a sharp look at how B2B marketers can cut through the noise, earn attention, and actually get people to respond.

Timestamps

• (00:17) - — Jess welcomes everyone

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:

Optimizely - the AI platform for marketers. Build your own AI agents or pull from a directory of 50+ pre-built ones for marketing use cases. Their new Virtual Teammates can join meetings, complete tasks, support campaigns, and keep your website optimized. Learn more at optimizely.com/exitfive.

Webflow - A website platform built for the agentic web, letting modern marketing teams build fully custom sites that perform in AI search with no developer needed. Learn more at webflow.com/for/exitfive.

Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive.

Compound Growth Marketing - A full-funnel demand gen agency helping high-growth cybersecurity and enterprise software companies show up earlier in the buying journey, combining AEO, modern paid advertising, and a dedicated go-to-market engineering team. Podcast listeners get two free media planning sessions to find out what channels are driving the best ROI. Learn more at compoundgrowthmarketing.com/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

#311: Dave goes solo this week (his decision, he said give me the mic; but Dan is also on him about podcast downloads around the holidays) with a quick November breakdown from real life - recapping the Exit Five team trip to Arizona, a big leadership update at the company, and covering five timeless marketing principles that matter more than ever (if you care about fighting AI slop). He also talks about recovering from hip surgery (everyone’s been asking how old he is), what he’s been reading, and a Thanksgiving food debate.

Timestamps

• (00:00) - - Intro + the sunglasses bit

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:

Optimizely - the AI platform for marketers. Build your own AI agents or pull from a directory of 50+ pre-built ones for marketing use cases. Their new Virtual Teammates can join meetings, complete tasks, support campaigns, and keep your website optimized. Learn more at optimizely.com/exitfive.

Webflow - A website platform built for the agentic web, letting modern marketing teams build fully custom sites that perform in AI search with no developer needed. Learn more at webflow.com/for/exitfive.

Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive.

Compound Growth Marketing - A full-funnel demand gen agency helping high-growth cybersecurity and enterprise software companies show up earlier in the buying journey, combining AEO, modern paid advertising, and a dedicated go-to-market engineering team. Podcast listeners get two free media planning sessions to find out what channels are driving the best ROI. Learn more at compoundgrowthmarketing.com/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

#310 Category Creation | In this episode, Dave Gerhardt digs in with Josh Lowman, Founder & CEO of Gold Front, to unpack what “category creation” actually takes, why most companies get it wrong, and how the best brands win by owning a spot in the customer’s mind. They get into the four real paths to category leadership, the trap of “fake” category design, why vibe and soul still beat spreadsheets, and how personal development quietly powers great marketing. If you’re building a B2B brand and trying to stand out in a market that feels painfully same-same, this one hits exactly where you’re stuck.

Timestamps

• (00:00) - – Dave’s Intro

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:

Optimizely - the AI platform for marketers. Build your own AI agents or pull from a directory of 50+ pre-built ones for marketing use cases. Their new Virtual Teammates can join meetings, complete tasks, support campaigns, and keep your website optimized. Learn more at optimizely.com/exitfive.

Webflow - A website platform built for the agentic web, letting modern marketing teams build fully custom sites that perform in AI search with no developer needed. Learn more at webflow.com/for/exitfive.

Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive.

Compound Growth Marketing - A full-funnel demand gen agency helping high-growth cybersecurity and enterprise software companies show up earlier in the buying journey, combining AEO, modern paid advertising, and a dedicated go-to-market engineering team. Podcast listeners get two free media planning sessions to find out what channels are driving the best ROI. Learn more at compoundgrowthmarketing.com/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

#309 Product Positioning | This episode is from a Drive 2025 (our annual Exit Five event) session with April Dunford (Founder, Ambient Strategy). April pulls from working with 300+ tech companies to unpack the real patterns behind winning positioning from calling out competitors’ nonsense to teaching buyers what actually matters, avoiding category-creation traps, and fixing the sales messes that weak positioning creates. It’s sharp, funny, brutally honest, and basically a crash course in how to make your product unmistakably different in a market full of noise.

PS. Want to join us at Drive 2026?

Head over to exitfive.com/drive to join the waitlist for Drive 2026 and be the first to know when tickets go on sale.

Timestamps

• (00:00) - – Why Positioning Breaks

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:

Optimizely - the AI platform for marketers. Build your own AI agents or pull from a directory of 50+ pre-built ones for marketing use cases. Their new Virtual Teammates can join meetings, complete tasks, support campaigns, and keep your website optimized. Learn more at optimizely.com/exitfive.

Webflow - A website platform built for the agentic web, letting modern marketing teams build fully custom sites that perform in AI search with no developer needed. Learn more at webflow.com/for/exitfive.

Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive.

Compound Growth Marketing - A full-funnel demand gen agency helping high-growth cybersecurity and enterprise software companies show up earlier in the buying journey, combining AEO, modern paid advertising, and a dedicated go-to-market engineering team. Podcast listeners get two free media planning sessions to find out what channels are driving the best ROI. Learn more at compoundgrowthmarketing.com/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

#308 Sales Alignment | 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 join the waitlist for Drive 2026 and be the first to know when tickets go on sale.

Timestamps

• (00:00) - – Dave’s Intro

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:

Optimizely - the AI platform for marketers. Build your own AI agents or pull from a directory of 50+ pre-built ones for marketing use cases. Their new Virtual Teammates can join meetings, complete tasks, support campaigns, and keep your website optimized. Learn more at optimizely.com/exitfive.

Webflow - A website platform built for the agentic web, letting modern marketing teams build fully custom sites that perform in AI search with no developer needed. Learn more at webflow.com/for/exitfive.

Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive.

Compound Growth Marketing - A full-funnel demand gen agency helping high-growth cybersecurity and enterprise software companies show up earlier in the buying journey, combining AEO, modern paid advertising, and a dedicated go-to-market engineering team. Podcast listeners get two free media planning sessions to find out what channels are driving the best ROI. Learn more at compoundgrowthmarketing.com/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

#307 Building Community | In this episode Dave joined Ali Orlando Wert (Director of Content Marketing & Brand at Databox) on their podcast called Move the Needle. She did an interview with Dave focused on community building. They cover how Exit Five grew 80 percent by operating more like a startup than a Slack group. Dave gets into the truth of building community, why most companies should not launch one, how to measure brand without losing your mind, and why AI has everyone simultaneously energized and spiraling.

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:

Optimizely - the AI platform for marketers. Build your own AI agents or pull from a directory of 50+ pre-built ones for marketing use cases. Their new Virtual Teammates can join meetings, complete tasks, support campaigns, and keep your website optimized. Learn more at optimizely.com/exitfive.

Webflow - A website platform built for the agentic web, letting modern marketing teams build fully custom sites that perform in AI search with no developer needed. Learn more at webflow.com/for/exitfive.

Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive.

Compound Growth Marketing - A full-funnel demand gen agency helping high-growth cybersecurity and enterprise software companies show up earlier in the buying journey, combining AEO, modern paid advertising, and a dedicated go-to-market engineering team. Podcast listeners get two free media planning sessions to find out what channels are driving the best ROI. Learn more at compoundgrowthmarketing.com/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

#306 Executive Insights | This episode was recorded live at our annual event, Drive 2025. I hosted Sylvia LePoidevin (CMO, Kandji), Trinity Nguyen (CMO, UserGems), and Natalie Taylor (Head of Marketing, Capsule) for a leadership panel breaking down what’s working in B2B marketing. They get into events that reliably create pipeline, outbound that still converts, media plays LLMs keep citing, and the tactics they’ve stopped running (like generic webinars that no one shows up for).

Want to come to Drive next year? Head over to exitfive.com/drive to join the waitlist for Drive 2026 and be the first to know when tickets go on sale.

Timestamps

• (00:00) - – Intro + Drive 2025 context

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:

Optimizely - the AI platform for marketers. Build your own AI agents or pull from a directory of 50+ pre-built ones for marketing use cases. Their new Virtual Teammates can join meetings, complete tasks, support campaigns, and keep your website optimized. Learn more at optimizely.com/exitfive.

Webflow - A website platform built for the agentic web, letting modern marketing teams build fully custom sites that perform in AI search with no developer needed. Learn more at webflow.com/for/exitfive.

Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive.

Compound Growth Marketing - A full-funnel demand gen agency helping high-growth cybersecurity and enterprise software companies show up earlier in the buying journey, combining AEO, modern paid advertising, and a dedicated go-to-market engineering team. Podcast listeners get two free media planning sessions to find out what channels are driving the best ROI. Learn more at compoundgrowthmarketing.com/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

#305 Influencer Marketing | This episode is a live session from Drive 2025 with Brianna Doe, where she breaks down why influence is now shaping every step of the buying journey, how smart B2B brands are borrowing plays from B2C, and what it really takes to build a creator program that doesn’t flame out on day one. She gets into the messy reality of picking the right creators and measuring impact without deluding yourself with vanity numbers.

Head over to exitfive.com/drive to join the waitlist for Drive 2026 and be the first to know when tickets go on sale.

Timestamps

• (00:00) - – Intro

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:

Optimizely - the AI platform for marketers. Build your own AI agents or pull from a directory of 50+ pre-built ones for marketing use cases. Their new Virtual Teammates can join meetings, complete tasks, support campaigns, and keep your website optimized. Learn more at optimizely.com/exitfive.

Webflow - A website platform built for the agentic web, letting modern marketing teams build fully custom sites that perform in AI search with no developer needed. Learn more at webflow.com/for/exitfive.

Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive.

Compound Growth Marketing - A full-funnel demand gen agency helping high-growth cybersecurity and enterprise software companies show up earlier in the buying journey, combining AEO, modern paid advertising, and a dedicated go-to-market engineering team. Podcast listeners get two free media planning sessions to find out what channels are driving the best ROI. Learn more at compoundgrowthmarketing.com/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

#304 | AI Buying Shift | This episode is from a recent Exit Five live session where I pulled together Lindsay O'Brien (Head of Marketing & Operations, Predictiv), Tom Wentworth (CMO, incident.io), and Aditya Vempaty (VP of Marketing, MoEngage) for a real talk on how AI is completely rewiring the B2B buying journey. We got into why buyers no longer need your pretty funnel, how AI-powered research changes the sales call, and what that means for your GTM strategy.

Timestamps

• (00:00) - – Intro + Dave Sets the Stage

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:

Optimizely - the AI platform for marketers. Build your own AI agents or pull from a directory of 50+ pre-built ones for marketing use cases. Their new Virtual Teammates can join meetings, complete tasks, support campaigns, and keep your website optimized. Learn more at optimizely.com/exitfive.

Webflow - A website platform built for the agentic web, letting modern marketing teams build fully custom sites that perform in AI search with no developer needed. Learn more at webflow.com/for/exitfive.

Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive.

Compound Growth Marketing - A full-funnel demand gen agency helping high-growth cybersecurity and enterprise software companies show up earlier in the buying journey, combining AEO, modern paid advertising, and a dedicated go-to-market engineering team. Podcast listeners get two free media planning sessions to find out what channels are driving the best ROI. Learn more at compoundgrowthmarketing.com/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

#303 Storytelling | This episode is from Drive 2025, our 2-day in-person event for B2B marketers in Burlington, VT. Harry Dry, creator of Marketing Examples and one of the best copywriters on the internet, shared a masterclass on storytelling, creativity, and writing marketing that actually connects—showing how to find great ideas, turn real stories into memorable campaigns, and make people feel something in the process.

Head over to exitfive.com/drive to join the waitlist for Drive 2026 and be the first to know when tickets go on sale.

Timestamps

• (00:00) - – Intro from Dave

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:

Optimizely - the AI platform for marketers. Build your own AI agents or pull from a directory of 50+ pre-built ones for marketing use cases. Their new Virtual Teammates can join meetings, complete tasks, support campaigns, and keep your website optimized. Learn more at optimizely.com/exitfive.

Webflow - A website platform built for the agentic web, letting modern marketing teams build fully custom sites that perform in AI search with no developer needed. Learn more at webflow.com/for/exitfive.

Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive.

Compound Growth Marketing - A full-funnel demand gen agency helping high-growth cybersecurity and enterprise software companies show up earlier in the buying journey, combining AEO, modern paid advertising, and a dedicated go-to-market engineering team. Podcast listeners get two free media planning sessions to find out what channels are driving the best ROI. Learn more at compoundgrowthmarketing.com/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