The Dave Gerhardt Show (from Exit Five)

Exit Five
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Interviews with top marketers sharing tactical tips, strategies, and lessons learned to help you grow your business. Hosted by Dave Gerhardt, founder of Exit Five, former CMO, and author of Founder Brand. Learn more at exitfive.com

  1. 8 HR AGO

    How to Upgrade Your Webinar and Email Strategy for 2026 with Jay Schwedelson (Founder, SubjectLine.com)

    #329 | Dave is joined by Jay Schwedelson, Founder of SubjectLine.com and GURU Media Hub, to break down why most webinars and email programs underperform and what to do instead. They talk about how packaging drives performance, why the word “webinar” kills registrations, and how small tweaks like renaming your session, shortening it to 22 minutes, or adding an “attend to receive” hook can dramatically increase show rates. Jay also shares tactical email plays, from using white space and tighter subject lines to increasing reply rates and improving inbox placement. Timestamps (00:00) - Why packaging matters more than the content (03:04) - Jay’s virtual event business and the GURU acquisition (05:50) - Why you should stop calling it a “webinar” (07:45) - The “attend to receive” tactic to boost show rates (10:19) - Why on-demand is hurting your engagement (14:28) - Why Fridays and Sundays outperform for B2B email + webinars (18:01) - How to choose webinar topics based on your goal (18:28) - Why 22-minute webinars and shorter podcasts win (29:15) - The white space + no preview text email hack (37:27) - The “reply with GUIDE” tactic to boost engagement (39:13) - 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

    42 min

  2. 1 DAY AGO

    The Strategy Behind Canva’s B2B Growth with Emma Robinson and Kristine Segrist

    #329 | Dave is joined by Emma Robinson, Head of B2B Marketing at Canva, and Kristine Segrist, Global Head of Consumer Marketing at Canva, to break down how Canva is scaling growth across both enterprise and consumer audiences. They talk about how Canva balances brand-building with pipeline accountability, how they turn bottom-up product adoption into enterprise deals, and why brand investment is a long-term growth lever. Emma and Kristine also share how their team structure, data science investments, and creative bets like the Love Your Work campaign help Canva scale without losing the brand identity that made them famous. Timestamps (00:00) - – Intro (03:21) - – Canva’s marketing org structure (06:21) - – Blurring B2B and B2C (11:21) - – How Canva measures marketing impact (16:21) - – Turning free users into enterprise deals (21:21) - – Data science’s role in marketing (24:21) - – Balancing brand bets with ROI (30:59) - – Inside the “Love Your Work” campaign (37:59) - – How Canva executes large campaigns (41:59) - – Building enterprise credibility and trust (44:59) - – FedEx case study on brand governance (48:59) - – Lessons from Google and Meta (52:59) - – Why creativity is a marketing superpower (54:59) - – Closing thoughts 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

    53 min

  3. 2 DAYS AGO

    How to Lead Marketing Through the AI Shift with Bill Glenn (SVP of Marketing at Esper)

    #328 | Jess Lytle is joined by Bill Glenn, SVP of Marketing at Esper, for a conversation about what it actually looks like to lead a marketing team through the AI shift. They talk about why most teams are still figuring AI out, how leaders should think about adoption beyond just tools, and why curiosity and experimentation matter more than having the “right” answers. Bill also shares how Esper is rolling out AI across the company with guardrails, the internal process they use to evaluate new tools, and why the biggest opportunity right now is using AI to eliminate busywork and unlock better thinking. Timestamps (00:00) - Why AI feels overwhelming for marketing leaders (04:06) - What Esper does and why software powering hardware matters (06:51) - Why AI feels like the early internet shift (08:41) - Leading with curiosity instead of pretending to be an AI expert (11:21) - Why AI adoption is a behavior change problem, not a tools problem (13:21) - How Esper is rolling out AI with guardrails across the company (19:06) - Why “boring AI” that saves time matters most (20:21) - Phase 1 vs Phase 2 AI adoption in marketing teams (32:09) - AI, mentorship, and preparing the next generation of marketers (44:54) - Leadership advice for first-time CMOs and VPs (49:59) - 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

    53 min

  4. 4 FEB

    How to Use AI for Content Without Creating Slop with Eoin Clancy (VP Growth at Airops)

    #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

    1 hr

  5. 29 JAN

    How To Drive Revenue Through Content with Lashay Lewis (Founder, Authority Plug)

    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

    48 min

  6. 27 JAN

    How Marketing Leaders are Thinking About AEO

    #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

    53 min

  7. 22 JAN

    How to Master B2B Positioning with Anthony Pierri (Fletch PMM)

    #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

    54 min

  8. 19 JAN

    How to Stand Out in B2B Marketing (with Louis Grenier, Author of Stand the F*ck Out)

    #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

    1h 2m
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Interviews with top marketers sharing tactical tips, strategies, and lessons learned to help you grow your business. Hosted by Dave Gerhardt, founder of Exit Five, former CMO, and author of Founder Brand. Learn more at exitfive.com

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