The Dave Gerhardt Show

#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 (06:14) - – Meet Jess Lytle, Head of Marketing at Exit Five (08:28) - – How Jess got hired at Exit Five (webinar → DMs → job) (10:28) - – From demand gen to AI: early adoption, teaching, and Lovable (15:58) - – Why AI feels different than traditional martech (18:28) - – Content in 2026: originality, human insight, and AI distribution (29:16) - – NotebookLM: real marketing workflows and internal use cases (35:16) - – AI tools, team structure, and hybrid marketer roles (45:56) - – 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:Optimizely - A no-code 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. AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. ***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 (04:28) - – Kieran’s career + the 2-year mission framework (09:58) - – The grind, early-career advice, and earning your stripes (12:28) - – Operator vs. manager + strong opinions in leadership (20:28) - – Why collaborative brainstorms fail (25:28) - – ChatGPT vs. Claude + how Kieran actually uses AI (33:16) - – Where AI is taking B2B marketing (answers → actions) (44:46) - – Picking a lane: technical vs. creative marketers (52:16) - – 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:Optimizely - A no-code 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. AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. ***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 (05:01) - – Panel intros: Dasha, Finn, Emeric (07:25) - – Why LinkedIn changed and why it matters now (09:34) - – “Our buyers aren’t on LinkedIn” is mostly wrong (12:26) - – Who should post: CEO, team, or company page (16:47) - – Why promo posts flop (and why that’s okay) (21:44) - – What to actually post when starting from zero (38:13) - – 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:Optimizely - A no-code 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. AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. ***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 (03:44) - – Personal update: hip surgery, burnout, and getting back in rhythm (05:44) - – The LinkedIn algorithm isn’t broken. Your content probably is (06:54) - – The big idea: attention is the real game in marketing (08:14) - – Lessons from Savannah Bananas and stealing ideas outside B2B (10:34) - – How Drift won by sucking the oxygen out of the market (12:54) - – Scrappy attention plays: billboards, protests, and founder brand (15:44) - – Why brand comes before product messaging (20:23) - – Listener Qs: playbooks, AI slop, and building real leverage (28:08) - – 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:Optimizely - A no-code 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. AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. ***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 (06:52) - Panel intros and GTM perspectives (09:22) - The real pipeline problem: growth without more headcount (11:52) - How teams use AI to identify in-market buyers earlier (17:22) - Buying groups, not leads: why account signals matter (21:22) - Predictive analytics, pipeline forecasting, and deal analysis (28:12) - Why traditional lead scoring is breaking (38:16) - How teams “swarm” accounts with marketing + sales (44:36) - 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:Optimizely - A no-code 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. AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. ***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