The Dave Gerhardt Show (from Exit Five)

#326 | Dave is joined by Eoin Clancy, VP of Growth at Airops, to break down what it takes to create great content without pumping out AI slop. They talk about the rise of the content engineer role and why more teams are hiring for it and three dead-giveaway signs content is low-quality AI generated. Eoin also shares why webinars are Airops’ best growth channel right now, including how they choose topics, source guests, why the sessions are ungated, and how to follow up in a way that drives revenue. A tactical episode for marketers trying to move faster with AI while keeping quality high.Timestamps(00:00) - Why AI content, content engineers, and webinars matter right now (03:44) - What Airops does and the AI search problem they’re solving (04:39) - What a “content engineer” actually is (16:19) - How to use AI without creating AI slop (19:35) - The 3 signals content is AI slop (34:23) - Why webinars are Airops’ best growth channel (36:48) - How they choose webinar topics and guests (53:00) - Other channels working (enablement, community, events) (56:00) - Final takeaways and wrap-up Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

325 | Lashay Lewis helps B2B SaaS companies create profit driven content strategies. We talk about why a B2B content strategy should be built from the bottom of the funnel up, why she interviews sales teams to understand "life before using the product" and why she interviews customer success teams to understand "life after using the product" and how that influences content strategy, how writing influences buyers, the power of a strong company POV, training in-house writers and freelancers in a way that scales, where podcasting fits in a B2B content strategy, why search volume can be misleading, and thoughts on how content marketers can use AI. Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

#324 | Dave is joined by three marketing leaders from different industries to talk on a live session about AI and SEO and what they've learned over the last year. Dave Steer (CMO at Webflow), Marcy Comer (CMO at EagleView) and Clare Schmitt (VP, Marketing & Communications at Piedmont Global) break down how buyers are learning about products through ChatGPT and why traditional SEO fundamentals still matter. The group shares real examples of how they’re approaching content, prompt tracking, PR, and brand authority, plus advice for marketers on where to focus, what to ignore, and how to guide their teams through this search shift.Timestamps(01:06) - Why AI + SEO is the hottest (and most confusing) topic in B2B marketing right now (05:14) - Meet the panel: marketing leaders from Webflow, EagleView, and Piedmont Global (08:52) - How AI search is changing buyer behavior vs traditional Google search (12:35) - EagleView’s real approach to AI search, greenfield opportunities, and prompt tracking (15:42) - What “black hat” vs “white hat” tactics look like in AI-driven search (19:49) - Webflow’s take: integrated marketing, generosity, and building useful tools (29:24) - Getting past high-level advice and into real execution (34:24) - “Circle the buyer”: how content builds demand before buyers are in-market (38:07) - Why PR is back: long-form press, citations, and brand credibility in AI search (45:07) - What to do if you’re a startup with no budget: focus on positioning first Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

#323 | Anthony Pierri from Fletch PMM joins Dave to talk about what actually matters in B2B positioning and messaging. They break down how to think about value props, why buyers don’t care about your features, and what makes a homepage instantly click. Anthony shares lessons on positioning from working with hundreds of early-stage B2B SaaS companies and explains how to connect real customer problems to clear outcomes. Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

#322 | Louis Grenier joins Dave for a conversation about what it actually takes to stand out in B2B marketing when everything feels the same. Louis sent Dave 10 surprise gifts to open during the show, and each one sparks a conversation about marketing, career, and life. They talk about the reality of how people decide to buy and why Louis is so focused on timeless fundamentals.Timestamps(00:00) - — Timeless marketing vs the AI hype (05:01) - — The colonoscopy story. (12:21) - — Trojan Horse marketing. Get attention first. Sell later. Stop leading with your product. (17:21) - — Why you can’t create demand, only redirect it. (23:01) - — Category creation vs sub-categories. Most startups get this wrong. (25:51) - — Meaning-free brand assets. Why weird mascots and visuals actually work. (33:09) - — How to sell bold ideas internally without asking for permission. (36:59) - — Ads that look like ads fail. Attention is the job. (45:39) - — Triggers vs pain points. How people actually decide to buy. (50:59) - — First principles, repetition, history, and why this stuff still works no matter the tech wave. Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

#321 | Jess Cook, VP of Marketing at Vector, joins Dave to break down what’s actually working in early-stage B2B marketing. They dig into how she thinks about attribution for brand channels, how Vector's podcast became a top marketing channel, why they created a brand mascot, and details on what content strategy is working on LinkedIn right now. They also cover shift from content leader to VP of Marketing and how to drive demand without a massive team or budget.Timestamps(03:06) - — Meet Jess Cook & What is Vector? (07:16) - — B2B Influencer pilot setup: why this channel, why now (14:34) - — The result: 45 demos, ~$1.1M pipeline, and how she tracked it (16:32) - — How to run influencers (21:57) - — Scaling idea: retainer-style influencer partnerships (25:51) - — Vector’s podcast: “awareness magnet” and the format that works (28:15) - — The production system: in-person batch recording a full season in 2 days (42:01) - — Jess’s LinkedIn strategy: why she started posting and what she optimizes for (53:49) - — Content → VP shift: the two muscles she’s building (metrics + leadership) Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

#320 | Matt Carnevale, Head of Community at Exit Five, joins Dave for a discussion about community building. They dive into a bunch of the lessons learned from building the Exit Five community over the last few years, including specific plays like onboarding, matchmaking, and moderation. If you’re thinking about community building in 2026, this is a good primer; plus the guys give their opinion on what “community” actually means and whether you should build a private community like Exit Five or focus more broadly on community building.Timestamps(00:02) - – Matt’s path from BDR to Head of Community at Exit Five (08:06) - – What “community” actually means (and what it definitely isn’t) (12:51) - – Why most B2B communities fail before they ever get traction (17:31) - – Community vs. content: what gets people in vs. what makes them stay (22:06) - – Why Slack groups aren’t a strategy (26:51) - – Treating community like a product, not a marketing channel (34:39) - – The role of trust, curation, and saying no to the wrong people (40:14) - – What community managers actually do behind the scenes (47:09) - – How in-person events changed the Exit Five community (53:19) - – The biggest lessons Matt’s learned after two years building Exit Five Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

#319 | Dave sits down with Jess Lytle, Head of Marketing at Exit Five, to talk about how AI is changing the job of B2B marketers and the reality of how AI is actually being adopted internally. They also cover how AI even helped Jess get her job at Exit Five and why she’s become obsessed about deploying AI in marketing and really believes this is the most important martech wave yet. Timestamps(00:00) - – Goals, manifestation, and reverse-engineering outcomes (05:51) - – Meet Jess Lytle, Head of Marketing at Exit Five (08:05) - – How Jess got hired at Exit Five (webinar → DMs → job) (10:05) - – From demand gen to AI: early adoption, teaching, and Lovable (15:35) - – Why AI feels different than traditional martech (18:05) - – Content in 2026: originality, human insight, and AI distribution (29:07) - – NotebookLM: real marketing workflows and internal use cases (35:07) - – AI tools, team structure, and hybrid marketer roles (45:47) - – Working at Exit Five, founder-led marketing, and brand bets Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

#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 (04:05) - – Kieran’s career + the 2-year mission framework (09:35) - – The grind, early-career advice, and earning your stripes (12:05) - – Operator vs. manager + strong opinions in leadership (20:05) - – Why collaborative brainstorms fail (25:05) - – ChatGPT vs. Claude + how Kieran actually uses AI (33:07) - – Where AI is taking B2B marketing (answers → actions) (44:37) - – Picking a lane: technical vs. creative marketers (52:07) - – The future CMO + agencies, in-person, and what still matters Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

#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 (04:38) - – Panel intros: Dasha, Finn, Emeric (07:02) - – Why LinkedIn changed and why it matters now (09:11) - – “Our buyers aren’t on LinkedIn” is mostly wrong (12:03) - – Who should post: CEO, team, or company page (16:24) - – Why promo posts flop (and why that’s okay) (21:21) - – What to actually post when starting from zero (38:04) - – Why thought leader ads outperform everything else Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

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 (03:21) - – Personal update: hip surgery, burnout, and getting back in rhythm (05:21) - – The LinkedIn algorithm isn’t broken. Your content probably is (06:31) - – The big idea: attention is the real game in marketing (07:51) - – Lessons from Savannah Bananas and stealing ideas outside B2B (10:11) - – How Drift won by sucking the oxygen out of the market (12:31) - – Scrappy attention plays: billboards, protests, and founder brand (15:21) - – Why brand comes before product messaging (20:14) - – Listener Qs: playbooks, AI slop, and building real leverage (27:59) - – Final takeaway: stop being boring, earn attention first Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

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 (06:29) - Panel intros and GTM perspectives (08:59) - The real pipeline problem: growth without more headcount (11:29) - How teams use AI to identify in-market buyers earlier (16:59) - Buying groups, not leads: why account signals matter (20:59) - Predictive analytics, pipeline forecasting, and deal analysis (27:49) - Why traditional lead scoring is breaking (38:07) - How teams “swarm” accounts with marketing + sales (44:27) - Brand and demand together: building future pipeline Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

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 (05:51) - – Dave’s background and path into marketing (10:06) - – What Dave is world-class at (and why copy is the leverage) (14:41) - – Why hooks come first and editing beats writing (20:01) - – How podcasting sharpened Dave’s instincts (25:31) - – Formatting, focus, and making writing easier to read (33:14) - – Deciding when something is “done” and when to ship (39:44) - – Why most B2B marketing fails by trying to say too much (46:29) - – Raising the bar, big bets, and making hard leadership calls Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

#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 (08:29) - – Early career lessons and building marketing from zero (15:29) - – How Gong found product-market fit and nailed positioning early (19:39) - – Courageous Marketing: why Udi wrote it and what it really means (23:29) - – Brand first: personality, positioning, then visuals (28:59) - – Campaigns that punched above their weight (billboards, experiments, perception hacks) (35:49) - – Proving brand impact: soft ROI, pipeline, and exec buy-in (48:19) - – The future: product-led marketing, AI, and courageous teams Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

#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 (02:43) - — Why email and messaging aren’t dead… bad messaging is (06:11) - — How AI changed the inbox and why standing out is harder than ever (06:47) - — Why human senders beat brand senders in email (10:16) - — Writing emails like you were invited into someone’s personal space (12:31) - — Balancing stakeholder requests vs. what your audience actually wants (15:41) - — Real talk on AI personalization, enrichment, and where it actually works (21:46) - — Subject lines, preview text, and how people really decide what to open (23:21) - — Email stories and empathy-driven content that outperform (29:16) - — SMS, in-app, and email orchestration: what to use when (36:59) - — Measuring impact when email is assist, not hero (44:59) - — The future: AI-driven workflows, data challenges, and what’s coming (53:39) - — Favorite tools (Claude, NotebookLM, etc.) and how people use them Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

#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 (04:21) - - Getting back into podcasting + November setup (05:51) - - The 5 timeless marketing principles (14:41) - - How to apply those principles in real marketing (15:51) - - Exit Five team trip to Arizona (17:41) - - Why in-person time matters (21:59) - - Dave’s hip surgery and recovery (24:29) - - What he read and watched in November (27:59) - - The Thanksgiving overrated/underrated debate (30:19) - - 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/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

#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 (03:35) - – Why Category Creation Got So Noisy (07:53) - – The Real Goal: Becoming Irreplaceable (12:39) - – How Customers Actually Form Categories (17:08) - – The Four Paths to Category Leadership (23:26) - – The Trap of “Fake” Category Design (29:09) - – Product Reality vs. Marketing Narrative (36:11) - – Why Vibe, Soul, and Taste Still Win (42:25) - – Community as a Differentiator (47:02) - – Josh on Therapy, Mindset, and Creative Clarity (52:54) - – Final Takeaways for B2B Marketers Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

#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 (03:33) - – Teaching Buyers to Spot Competitor BS (07:01) - – Turning Differentiators into Real Value (10:39) - – The Trap of Overthinking Categories (14:26) - – Choosing Your Go-To-Market Before Your Positioning (19:03) - – Building a Story Only You Can Tell (23:31) - – When Great Storytelling Backfires (29:32) - – Positioning Multi-Product Companies (33:13) - – When and Why to Reposition (37:01) - – Bringing It All Together in Sales Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

#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 (03:47) - – Jen’s Story & Why She’s Here (06:37) - – The Real Enemy: Buyer Status Quo (10:44) - – The Shiny Object Era (14:44) - – How Status Quo Kills Deals (22:14) - – The Close-Lost Audit (30:09) - – The “We” Problem in Outbound (32:54) - – The Raincoat Example & Messaging Shift Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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

#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/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by: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.Optimizely - An AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive (PS - you'll get a FREE pair of Meta Ray Bans if you do). 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