The Exit Five Podcast

Latest Episodes:

Why B2B Marketers Need to Start Thinking Like Media Companies with Melissa Rosenthal Sep 08, 2026

Show notes

#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

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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.

Convertiv - A B2B marketing agency that helps enterprise teams build an AI-powered go-to-market strategy, specializing in AEO. Podcast listeners get a free AI search review showing how you stack up against competitors. Learn more at convertiv.com/exitfive.

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.

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.

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.

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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.
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Writing for Humans: The Real AI Workflows Behind Great B2B Content Sep 03, 2026

Show notes

#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

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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.

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B2B Ads that Don't Suck (with Shlomo Genchin, Unbore.com) Aug 31, 2026

Show notes

#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

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

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***

Brought to you by:

***

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

How to Win with Webinars: 5 B2B Marketing Pros Share Revenue-Driving Plays Aug 27, 2026

Show notes

#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:

***

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

Marketing to B2B buyers who aren't on LinkedIn (with Clare Corriveau, VP Marketing, Tekmetric) Aug 24, 2026

Show notes

#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:

***

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

YouTube for B2B Marketing (with Samu Kovács) Aug 20, 2026

Show notes

#383 | YouTube is the second-largest search engine on the planet, yet few B2B marketers know how to use it optimally. Dasha Shakov, the newest Exit Five podcast host, sits down with Samu Kovács, founder of the B2B YouTube agency KS Media, to unpack why he calls YouTube the hedge against AI slop. Samu breaks down the research process his team runs before writing a script, what belongs in a hook that keeps people watching, and how clients repurpose high-performing LinkedIn posts into YouTube videos instead of starting from zero. They also cover the realistic 90-day timeline for results, how to tell if YouTube is lifting your other channels, and the exact AI stack his team uses for scripting and thumbnails.

Timestamps

(00:00) - - Why YouTube is B2B marketing's hedge against AI slop
(02:19) - - Who hires a B2B YouTube agency, and why YouTube still scares most marketers
(06:26) - - The direct and indirect ROI of nailing YouTube
(08:33) - - Where YouTube fits in the funnel, and when a niche is too small for it
(13:33) - - Mapping ICP pain points, then reverse-engineering proven video formats
(19:54) - - Doing the research yourself, and diagnosing a failed YouTube strategy
(22:39) - - The hook, the structure, and repurposing LinkedIn content into scripts
(33:09) - - Publishing cadence and the realistic 90-day timeline
(35:44) - - Shortening sales cycles and proving YouTube's impact across channels
(39:42) - - Where AI fits in the process, from research to scripting to editing
(44:22) - - Samu's exact AI model stack

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:

***

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

From Startup to IPO: How the CMO of Varonis Has Kept the Same Job for 15 Years, ft. Rob Sobers Aug 17, 2026

Show notes

#382 | Rob Sobers has been CMO of Varonis for 15 years - through its growth from startup to public company doing over $700 million in revenue. Dave talks with Rob about how he's stayed sharp enough to keep the job this long, starting with the fact that as an engineer, he still writes JavaScript and even fixes bugs on the Varonis website from time to time. Rob explains why no manager on his team oversees work they don't do themselves, why he'd rather keep marketing simple than layer on complexity as the company scales, and his "reasonableness test" for deciding which programs don't need to be forced into a pipeline number. They also cover his approach to saying no to his own team, and why longevity gives him a wider lens on the business.

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Timestamps

(00:00) - - Meet Rob Sobers, CMO of Varonis for 15 years
(01:18) - - Why Rob still writes JavaScript and fixes bugs on the website
(05:06) - - Learning a new marketing discipline every time he was out of his depth
(05:55) - - Why there are no career middle managers on the Varonis marketing team
(07:24) - - The communication tax of overstaffing a team
(09:59) - - Keeping goals dead simple: opportunity creation as the north star metric
(14:28) - - Getting good at saying no to his own team, but not too good
(18:02) - - The reasonableness test: why not everything needs a pipeline number
(20:49) - - Reverse-engineering the marketing budget from the revenue number
(23:04) - - What separates a CMO from a VP of Marketing
(26:26) - - The ClickUp $1M "one-person marketing team" debate
(35:26) - - Marketing to skeptical CISOs, acquisitions, and why B2B brands need a mascot

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:

***

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

The Strategy Behind Canva’s B2B Growth with Emma Robinson and Kristine Segrist Aug 13, 2026

Show notes

#381 | Dave sits down with Emma Robinson, Head of B2B Marketing at Canva, and Christine Siegrist, VP of Consumer Marketing at Canva, to talk about how the two teams operate as one org instead of fighting over lead credit. They get into Canva's matrixed structure across consumer, B2B, and international, how signals from free users turn into team and enterprise upgrades, and why Canva built a dedicated data science team so marketers can make bigger creative bets instead of smaller, "provable" ones. They also unpack the Love Your Work campaign, why out-of-home ads make a consumer brand feel legitimate to enterprise buyers, and the lessons Emma and Christine carried over from their time at Google and Meta.

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:

***

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

60-Minute B2B Blitz Part 2: 8 Marketers Share Their Best Plays from 2026 (So Far) Aug 10, 2026

Show notes

#380 | Eight B2B marketers get two minutes each to pitch the single best marketing play they ran this year - and the crowd votes on who moves forward. Dave Gerhardt and Dasha Shakov hosts the second round of the Exit Five B2B Marketing Blitz, and this episode covers a lot of ground: updating old blog content to win AI search citations, turning product into research that got a company's CEO in front of Congress, an AI agent that rewrites website copy for different buyer personas, why LinkedIn articles are quietly dominating AI search results, scaling influencer marketing from a tiny four-creator pilot, a multi-channel brand campaign built around customer wins, and how one team turned a physical book into a 65x return on target accounts closed. Tune in to find out who makes it through to the second round, and who was ultimately crowned the Blitz MVP.

Timestamps

(00:00) - - The B2B marketing Blitz kicks off
(03:56) - - Turning sales, success, and support calls into content gold
(06:48) - - Updating old blog content to win AI search citations
(08:58) - - Using your own product to get your CEO in front of Congress
(11:09) - - An AI agent that rewrites content for different buyer personas
(15:38) - - Why LinkedIn articles are winning AI search citations
(17:49) - - Scaling influencer marketing from a tiny pilot to a full program
(20:18) - - A multi-channel brand campaign built around customer wins
(22:39) - - Turning a physical book into a 65x return on target accounts
(26:43) - - The exact AI workflow behind the content optimization play
(35:40) - - The specific questions to ask sales, success, and support teams
(42:53) - - Following up a book launch with an account-based magazine

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:

***

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

How to Talk to Finance About Marketing Budget with Patrick Shea (Global Head of Marketing at BlueVoyant) Aug 06, 2026

Show notes

#379 | Dave sits down with Patrick Shea, SVP of Global Marketing at BlueVoyant, to discuss how enterprise marketing really works inside a $175 million cybersecurity company built heavily on partnerships. Patrick breaks down the difference between hyperscaler tech alliances and reseller partnerships, how BlueVoyant defines and qualifies leads by account rather than volume, and why he treats partnership stakeholders like a market of their own. They also get into the cost-per-opportunity formula Patrick uses to win budget back from finance, why he's trying to kill long-term planning in favor of annual focus areas and the wild HubSpot coincidence that made him responsible for Dave's success.

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:

***

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

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