The Exit Five Podcast

Latest Episodes:

The Future of B2B Marketing with Kieran Flanagan Jan 05, 2026

Show notes

#318 | Dave is joined by Kieran Flanagan, SVP of Marketing at HubSpot and former CMO at Zapier. They break down how AI is reshaping B2B marketing workflows, content creation, and team structure, plus Kieran’s leadership philosophy for managing a 300+ person team while staying deeply involved in creative execution. This episode offers a clear look at how AI is changing the game and how B2B marketers can stay creative, strategic, and indispensable in the process.

Timestamps

(00:00) - – Intro + why AI matters now
(02:44) - – Kieran’s career + the 2-year mission framework
(08:14) - – The grind, early-career advice, and earning your stripes
(10:44) - – Operator vs. manager + strong opinions in leadership
(18:44) - – Why collaborative brainstorms fail
(23:44) - – ChatGPT vs. Claude + how Kieran actually uses AI
(30:08) - – Where AI is taking B2B marketing (answers → actions)
(41:38) - – Picking a lane: technical vs. creative marketers
(49:08) - – The future CMO + agencies, in-person, and what still matters

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:

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.

***

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 Master LinkedIn for B2B Jan 01, 2026

Show notes

#317 | Dave hosts a live session with Dasha Shakov (Head of Marketing, Proton.ai), Emeric Ernoult (Founder, CEO, Agorapulse), and Finn Thormeier (Founder, Project 33) to break down what’s working on LinkedIn right now. They discuss why LinkedIn is the most important channel for B2B, why social media is the best marketing channel available today, how founder-led and employee content drives growth, and what’s changed about how people use the platform over the last five years. The group also gets into LinkedIn’s thought leader ads, thoughts on measuring results when attribution is messy, and how to sell LinkedIn’s value to leadership and convince them to spend time there. It’s a look into how B2B teams can earn attention, build credibility, and make LinkedIn a massive growth channel in 2026.

Timestamps

(00:56) - – Why LinkedIn is still Dave’s favorite B2B channel
(03:17) - – Panel intros: Dasha, Finn, Emeric
(05:41) - – Why LinkedIn changed and why it matters now
(07:50) - – “Our buyers aren’t on LinkedIn” is mostly wrong
(10:42) - – Who should post: CEO, team, or company page
(15:03) - – Why promo posts flop (and why that’s okay)
(20:00) - – What to actually post when starting from zero
(35:05) - – Why thought leader ads outperform everything else

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 Build a Brand People Pay Attention To Dec 29, 2025

Show notes

316 | In this episode, Dave breaks down how the best companies win by standing out through smart ideas, creative execution, and consistent attention. He pulls lessons from Drift, Savannah Bananas, and his own wins to show why ideas matter, why brand is a durable long-term advantage, and how strong content can still break through today. Plus: thoughts on AI slop, why LinkedIn can be a powerful channel when used well, leadership lessons from The Hard Thing About Hard Things, and rapid-fire listener questions on playbooks, thought leadership, and building something bigger than Exit Five.

Timestamps

(00:00) - – Why attention became a dirty word in marketing
(02:00) - – Personal update: hip surgery, burnout, and getting back in rhythm
(04:00) - – The LinkedIn algorithm isn’t broken. Your content probably is
(05:10) - – The big idea: attention is the real game in marketing
(06:30) - – Lessons from Savannah Bananas and stealing ideas outside B2B
(08:50) - – How Drift won by sucking the oxygen out of the market
(11:10) - – Scrappy attention plays: billboards, protests, and founder brand
(14:00) - – Why brand comes before product messaging
(17:15) - – Listener Qs: playbooks, AI slop, and building real leverage
(25:00) - – Final takeaway: stop being boring, earn attention first

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 Marketing Teams Are Using AI to Drive Pipeline Dec 25, 2025

Show notes

315 | Jess Lytle (Head of Marketing at Exit Five) hosts a live roundtable with Morgan Cole (VP of Demand Gen at Red Canary), Lisa Cole (CMO at 2X), and Jean Cameron (Sr. Director of Field & Partner Marketing at Demandbase) on how B2B teams are using AI to drive pipeline and revenue. They share real examples of how marketers are identifying in-market buyers earlier, moving deals faster, replacing outdated lead scoring, and keeping marketing, sales, and ops aligned around revenue. The conversation goes deep on intent signals, buying groups, predictive analytics, brand vs demand, and what’s changing in the new era of pipeline accountability.

Timestamps

(00:00) - AI hype vs real revenue impact
(05:08) - Panel intros and GTM perspectives
(07:38) - The real pipeline problem: growth without more headcount
(10:08) - How teams use AI to identify in-market buyers earlier
(15:38) - Buying groups, not leads: why account signals matter
(19:38) - Predictive analytics, pipeline forecasting, and deal analysis
(26:28) - Why traditional lead scoring is breaking
(35:08) - How teams “swarm” accounts with marketing + sales
(41:28) - Brand and demand together: building future pipeline

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 Write Great Marketing Copy (And Generate More Ideas, Faster) Dec 22, 2025

Show notes

314 | In this episode, Dmitry Shamis sits down with Dave to break down how Dave writes—the process behind emails, newsletters, landing pages, and posts that get attention. They talk about why Dave starts with the hook, why editing matters more than writing, and why most B2B marketing fails by trying to say too much. Dave also shares how podcasting shaped his thinking, why formatting is underrated, how he decides when something is “done,” and why shipping beats waiting for perfection. If you want to learn more behind Dave’s writing, creation, and marketing this episode is a great one for you; Dave shares a bunch of his behind the scenes style that he’s not shared on the podcast before.

What’s Your Process?is hosted by Dmitry Shamis—co-founder of OhSnap!, former Head of Brand and Creative at HubSpot, and one of the early pioneers of self-service brand systems for B2B tech. The show is an in-depth look at the processes behind top marketers, with past guests including Jess Cook, Ross Simmonds, Eddie Shleyner, Lashay Lewis, and Melissa Rosenthal.

Timestamps

(00:00) - – Why this conversation matters
(04:30) - – Dave’s background and path into marketing
(08:45) - – What Dave is world-class at (and why copy is the leverage)
(13:20) - – Why hooks come first and editing beats writing
(18:40) - – How podcasting sharpened Dave’s instincts
(24:10) - – Formatting, focus, and making writing easier to read
(30:15) - – Deciding when something is “done” and when to ship
(36:45) - – Why most B2B marketing fails by trying to say too much
(43:30) - – Raising the bar, big bets, and making hard leadership calls

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 Standout in B2B with Udi Ledergor, Chief Evangelist at Gong Dec 18, 2025

Show notes

#313 | In this episode, Udi Ledergor joins Dave to break down the ideas behind his new book, Courageous Marketing, and why most B2B marketing fails because it plays it safe. He also shares his journey from marketer #1 to CMO to Chief Evangelist at Gong, where he led category creation, brand, and marketing through massive scale. They unpack how Gong built a brand that actually stood out, what it means to punch above your weight as a B2B marketer, and how to think about brand ROI without fake dashboards.

Timestamps

(00:00) - – Meet Udi and his path into marketing
(07:08) - – Early career lessons and building marketing from zero
(14:08) - – How Gong found product-market fit and nailed positioning early
(18:18) - – Courageous Marketing: why Udi wrote it and what it really means
(22:08) - – Brand first: personality, positioning, then visuals
(26:00) - – Campaigns that punched above their weight (billboards, experiments, perception hacks)
(32:50) - – Proving brand impact: soft ROI, pipeline, and exec buy-in
(45:20) - – The future: product-led marketing, AI, and courageous teams

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 Do Better Email Marketing Dec 15, 2025

Show notes

#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
(01:22) - — Why email and messaging aren’t dead… bad messaging is
(04:50) - — How AI changed the inbox and why standing out is harder than ever
(05:26) - — Why human senders beat brand senders in email
(08:55) - — Writing emails like you were invited into someone’s personal space
(11:10) - — Balancing stakeholder requests vs. what your audience actually wants
(14:20) - — Real talk on AI personalization, enrichment, and where it actually works
(20:25) - — Subject lines, preview text, and how people really decide what to open
(22:00) - — Email stories and empathy-driven content that outperform
(27:55) - — SMS, in-app, and email orchestration: what to use when
(34:00) - — Measuring impact when email is assist, not hero
(42:00) - — The future: AI-driven workflows, data challenges, and what’s coming
(50:40) - — Favorite tools (Claude, NotebookLM, etc.) and how people use them

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

Five Marketing Principles That Matter More Than AI Dec 11, 2025

Show notes

#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
(03:00) - - Getting back into podcasting + November setup
(04:30) - - The 5 timeless marketing principles
(13:20) - - How to apply those principles in real marketing
(14:30) - - Exit Five team trip to Arizona
(16:20) - - Why in-person time matters
(19:00) - - Dave’s hip surgery and recovery
(21:30) - - What he read and watched in November
(25:00) - - The Thanksgiving overrated/underrated debate
(27:20) - - Big news: Dan promoted to CEO and what’s next for Exit Five

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 be Irreplaceable in B2B Marketing (with Josh Lowman) Dec 08, 2025

Show notes

#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
(02:14) - – Why Category Creation Got So Noisy
(06:32) - – The Real Goal: Becoming Irreplaceable
(11:18) - – How Customers Actually Form Categories
(15:47) - – The Four Paths to Category Leadership
(22:05) - – The Trap of “Fake” Category Design
(27:48) - – Product Reality vs. Marketing Narrative
(33:12) - – Why Vibe, Soul, and Taste Still Win
(39:26) - – Community as a Differentiator
(44:03) - – Josh on Therapy, Mindset, and Creative Clarity
(49:55) - – Final Takeaways for B2B Marketers

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 Make Your Product Positioning Impossible to Ignore with April Dunford (Founder, Ambient Strategy) Dec 04, 2025

Show notes

#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
(02:12) - – Teaching Buyers to Spot Competitor BS
(05:40) - – Turning Differentiators into Real Value
(09:18) - – The Trap of Overthinking Categories
(13:05) - – Choosing Your Go-To-Market Before Your Positioning
(17:42) - – Building a Story Only You Can Tell
(22:10) - – When Great Storytelling Backfires
(26:33) - – Positioning Multi-Product Companies
(30:14) - – When and Why to Reposition
(34:02) - – Bringing It All Together in Sales

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

Our TOPPODCAST Picks

Follow Us

Stay Connected

Related Podcasts

Links

Stay Connected