The Dave Gerhardt Show (from Exit Five)

#388 | Dave sits down with Melissa Rosenthal, co-founder of Outlever and former CCO at ClickUp, CRO at Cheddar, and VP of Creative at BuzzFeed, to talk about why most B2B content strategies fail because they're measured like ad campaigns instead of built like an actual media outlet. Melissa breaks down how she trains writers to think like journalists instead of bloggers, why third-party trade publications tend to outperform company blogs, and what it actually takes to run a media operation instead of just posting content. They also get into her wild LinkedIn distribution playbook - five posts a day, no rules followed - and whether AI can ever replace real editorial judgment.
Timestamps

(00:00) - - Today's guest: Melissa Rosenthal, co-founder of Outlever

(01:58) - - From Buzzfeed to Cheddar to ClickUp

(06:33) - - Why most B2B content strategies get abandoned too soon

(09:20) - - The B2B companies actually winning at content right now

(10:32) - - What building a real media company looks like from the inside

(12:22) - - Training writers to think like journalists, not bloggers

(16:48) - - Should your content live on your own site or somewhere else

(21:57) - - Why separating the newsroom from marketing makes content credible

(24:55) - - Her LinkedIn playbook: five posts a day and breaking every rule

(26:23) - - Why the biggest wins never show up in the analytics

(28:36) - - The obvious question nobody in B2B wants to answer

(32:18) - - Can AI ever replace real editorial judgment

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

#387 | Six B2B marketers share tactical plays for using AI to make content that doesn't sound like AI. This Exit Five Live session breaks down a set of specialized agents that lifted blog traffic 700% in six months, a 23-step agent that researches and writes AEO content straight into WordPress, and the winning play: turning original survey data into an ownable narrative. Also on the agenda: a structured review process that replaces vibes-only QA, a Claude skill trained on stakeholder feedback so drafts land pre-aligned, and five rules for using AI to learn faster without outsourcing your thinking. One thing the full group agreed on: the human stays in the loop.

Timestamps
(00:00) - - Intro and the Exit Five Live Format

(03:47) - - Meet the Lineup

(07:38) - - Build a Digital Team of Specialized AI Agents

(14:33) - - Before the Prompt and After the Prompt

(21:42) - - A 23-Step Agent That Writes AEO Content for LLMs

(30:11) - - Turn Original Research Into a Content Differentiator

(33:20) - - Treat Your Edits as Training Data

(35:55) - - Faster to Content and Faster to Internal Buy-In

(43:19) - - Rules for Learning With AI

(49:16) - - The Winning Play

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

#386 | When your ad budget is zero but your creative ambition isn't, three simple techniques can still make you scroll-stopping. Dasha Shakov sits down with Shlomo Genchin, founder of unbore.com, the "unofficial school for B2B ads," to break down what actually makes a B2B ad good. Shlomo walks through his two-part research process for beating the blank page, then unpacks three frameworks - A World Without, Visual Analogy, and Personification - behind some of his highest-performing client campaigns. They also get into hiring actors on a budget, winning over a nervous CEO, and why Shlomo believes advertising should follow culture instead of trying to lead it. Plus his honest take on where AI actually helps and where it still falls flat.
Tools & swipe files
reddit.com/answers
adfolio.design
blackcamel.agency/b2b-video-ads-library
Ads referenced (but not shown)
Fibbler’s AI ad

Timestamps

(00:00) - - Welcome: Shlomo Genchin

(01:51) - - How ad school and B2B's "Wild West" pulled Shlomo out of the agency world

(07:05) - - Beating the blank page: practical research vs. personal research

(13:15) - - The biggest myths about creativity, and how to "steal like an artist"

(16:29) - - The three pillars of a great B2B ad, and technique #1: World Without

(21:35) - - Technique #2: Visual analogy, and why a winning ad can run for years

(29:45) - - Technique #3: Personification, and how to hire actors on a budget

(38:05) - - Getting a nervous leadership team to say yes to a fun idea

(42:04) - - AI philosophy: why advertising should follow culture, not lead it

(46:11) - - The highest-leverage move for a team with zero ad budget

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

#385 | Five B2B marketers share their single best-performing webinar play - with the real numbers to back it up. This Exit Five Live session breaks down the exact tactics behind a signup flow that 5x'd conversions, a post-webinar follow-up system that closed $1M in pipeline in a week, and a series format built to compound results instead of resetting with every session. You'll also get a look at running a webinar program like an in-person conference, and how to borrow an influencer's audience to solve the cold-start problem. Real plays, receipts, and step-by-step mechanics you can steal for your own program.
Timestamps

(00:00) - - Why Exit Five Live exists, and today's webinar bracket format

(06:01) - - Turning the thank-you page into a qualifying survey to 5x conversions

(13:06) - - Building a webinar series that compounds instead of resetting each time

(20:01) - - The post-webinar follow-up system that closed $1M in pipeline in a week

(23:14) - - Building AI agents to personalize that follow-up at scale

(27:31) - - Structuring a webinar series like an in-person conference

(33:09) - - Borrowing an influencer's audience to solve the cold-start problem

(35:55) - - Automating content repurposing from one webinar transcript

(40:09) - - Why first-party research is the real lead magnet

(40:49) - - Live vote, the winning play, and closing announcements

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

#384 | A lot of people say B2B marketing is boring - those people couldn't possibly be in B2B. Take Clare Corriveau, VP of Marketing at Tekmetric: her buyer is an auto repair shop owner who isn't on LinkedIn, doesn't check email, and isn't downloading anything. Clare walks through how Tekmetric built its messaging around a founder who ran a shop for a decade, why every new hire visits an actual shop before touching a campaign, and how peer groups and an unmanaged 6,000-member Facebook community became a real lever in the company's growth engine. This episode focuses on marketing to an overlooked B2B category, and the huge upside that comes with it. The opportunity is anything but boring.
Timestamps

(00:00) - - Why "boring" B2B categories are actually the biggest opportunity

(06:00) - - Why a founder who ran a shop for 10 years shapes every messaging decision

(11:00) - - Events at scale: 100+ a year, plus a 1,000-person first-time conference

(17:00) - - What the VP of Marketing job really is

(21:00) - - Hiring humans when everyone is saying AI will replace them

(24:00) - - Betting on channels the team almost skipped: Bing and Facebook

(26:00) - - Peer groups and a 6,000 member Facebook community

(30:00) - - How to get customers to love, support, and defend your brand

(37:00) - - The real competitor is status quo

(38:00) - - Why new hires visit a real shop before they touch a campaign

(45:00) - - The opportunity: 5% market share in a category growing 50% a year

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