The Dave Gerhardt Show (from Exit Five)

#337 | Dave sits down with Erin May, CMO at User Interviews, who joined as the company's first marketer with a two-page website and zero recurring revenue and helped grow it to $20M+ ARR over eight years. Erin breaks down how she picked one niche audience and went all in, why she led with ungated content, and how she built a quarterly operating rhythm around "Bangers," tentpole marketing moments that get the entire company involved. They also get into podcasting ROI, what she'd do differently with AI-driven search today, and why she thinks the brand vs. demand debate is just noise.Timestamps(00:00) - Intro: 8 years, one niche, a two-page website, and $20M ARR (05:16) - How Erin identified the right audience to go all in on (07:18) - Building the UX Research Field Guide and the early SEO strategy (09:47) - Why she went ungated and still captured 13% email conversion (13:28) - What she'd do differently with content strategy today (16:04) - Stacking channels one at a time instead of doing everything at once (18:43) - How to plan for the next phase of growth before you need it (21:14) - Introducing Bangers: the quarterly marketing OS (23:42) - Top of funnel vs. bottom of funnel Bangers (30:25) - How LinkedIn and employee advocacy fit into the Banger playbook (34:44) - Why Erin started a podcast seven years ago when no one else was (38:07) - How to think about podcast ROI when attribution is fuzzy (40:59) - AI expectations for her marketing team (45:27) - Why the brand vs. demand debate is stupid (48:39) - The real secret: making your customer the hero 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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

Eoin Clancy (VP of Growth at AirOps), Connor Beaulieu (Senior SEO Manager at LegalZoom), and Adina Timar (Head of AEO at Weflow) join this live session to talk about how to create high-quality content with AI. Connor walks through a workflow his team built at LegalZoom to automatically source expert quotes.. Adina shows how she rebuilds competitor pages from scratch using sales calls, LLM data, and live competitor analysis. And Eoin shares the research behind why content quality is now the single biggest lever in AI search. If you want to see what content engineering actually looks like in practice, this one is for you. 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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

#335 | Jeff Hardison, now VP of Product Marketing at Sanity, joined Dave when he was running product marketing at Calendly to break down what the product marketing role should actually look like inside a B2B company. They get into how Jeff structured his team to serve both a PLG motion and an enterprise sales team at the same time, why he hires for specialization instead of making everyone a generalist, and how he thinks about measuring a function that touches almost every team in the company. Jeff also shares his take on positioning and messaging, how to run product launches that actually rally the company, and the two interview questions he uses to figure out if someone will be happy in a product marketing role. 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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

#334 | Dave is joined by Jessica Serrano, CMO at Bagel Brands (Einstein Brothers, Noah's, Bruegger's, Manhattan Bagel), for a conversation about what B2B marketers can learn from consumer restaurant marketing. They discuss why consumer and B2B marketing are way more similar than people think, how she’s using AI across her marketing and sales process, and her philosophy that her job is to ‘build brand over time and drive sales overnight.’ Jessica shares how COVID forced Dig Inn to rebuild itself as an e-commerce business, how she built a B2B catering sales motion from scratch using HubSpot and buyer personas, and how filtering work emails out of a consumer list became a real customer acquisition tactic. Listen to this episode to learn tactics that work whether you're selling bagels or software.Timestamps(00:00) - Why a consumer CMO listens to B2B marketers (and vice versa) (03:33) - How COVID forced Dig Inn to rebuild as an ecommerce business overnight (06:55) - The math behind going after $500 catering orders vs. $15 walk-ins (10:33) - Building buyer personas for office admins, sports nutritionists, and universities (16:05) - Why Jessica switched from ChatGPT to Claude (and the breakthrough moment) (22:54) - Using AI for rapid product testing on a budget that wouldn't cover traditional research (30:06) - "Build the brand over time, drive sales overnight" and what that looks like at Bagel Brands (32:59) - Why you can't just copy a playbook from Taco Bell to Burger King (37:18) - The biggest lesson from working at brands with nearly 1,000 locations (40:46) - Google reviews as a source of truth for aligning marketing and operations (47:49) - Why organic-first content matters more in the age of AI and dead internet theory 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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

#333 | Dave is joined by Clare Schmitt, a seasoned marketing leader and a member of our CMO community, to walk through what it actually takes to lead a rebrand at a mid-market B2B company. Clare shares how she partnered with her CEO to drive a full rebrand, from hiring a naming agency and running an RFP, to managing a small decision-making council, rolling out the new brand across every department, and measuring success post-launch. If you're a marketing leader thinking about a rebrand, this episode is a practical, top to bottom playbook from someone who just did it.Timestamps(00:00) - Why rebrands come up and what this episode covers (02:58) - Clare's role at Piedmont Global and how the rebrand got started (05:13) - Should you hire a naming agency? What it costs and what they actually do (08:41) - Running an RFP and why they chose Focus Lab (09:27) - Why the CEO has to own the rebrand go-to-market (11:03) - Keeping the decision-making council small and who was in it (19:09) - How to get CEO buy-in: framing a rebrand as infrastructure, not a marketing initiative (21:46) - Timeline: how long a rebrand actually takes ($50M+ companies) (23:28) - The rollout: project management, execution, and building the website internally (25:25) - Measurement, post-launch QA, and tracking whether your narrative is sticking 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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

#332 | Dave is joined by Domi de Saint-Exupéry, CMO at Lemlist, a bootstrapped $40M ARR sales engagement platform, to break down exactly how she turned $1.2M in marketing spend into $31M in new ARR in 2025. Domi shares the full breakdown of every channel, agency, influencer strategy, and partnership play that drove results. This includes how they went from $0 to $500K in paid ads, why partnerships are the most underrated B2B growth channel, how they built a micro-influencer program, and what AI use cases are actually working (and which are overrated). If you want real numbers and real playbooks, this one's for you.Timestamps(00:00) - Introduction: $1.2M in spend, $31M in new ARR (03:33) - What Lemlist does and how the company got to $40M ARR (06:48) - Going from $0 to $500K in paid ads: what triggered the shift (11:03) - How to execute paid ads well: outsourcing vs. in-house, and scaling by channel (17:18) - LinkedIn ads creative: why "on-brand and safe" was the wrong approach (21:48) - Mistakes made in paid: Snapchat, Spotify, and channels that didn't work (25:18) - The micro-influencer playbook: how to find, brief, and measure creators (36:44) - How influencer content compounds with paid ads and outbound (the Julio story) (42:14) - Partnerships: why $450K went here and why it's the most underrated B2B channel (50:44) - AI in marketing: what's overrated (content generation) and what's actually working 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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

#331 | Dave is joined by a group of marketing leaders from Ramp, Snowflake, and Hightouch for a discussion about ABM and their plans for 2026. Casey Patterson (Director of ABM, Snowflake), Drew Pinta (Director of Growth Data Science, Ramp), and Brian Kotlyar (CMO, Hightouch) break down what ABM actually looks like in 2026 and what’s working right now inside of their companies. They share how they’re picking target accounts, aligning with sales, and building programs that go way beyond running ads. The group also digs into measurement, personalization, and how teams are using better data and AI to scale ABM without wasting budget. If you need a deeper dive on ABM tactics right now, this is the episode for youTimestamps(00:00) - - Why ABM is still a top topic in 2026 (04:28) - - Intros: Snowflake, Ramp, and Hightouch (07:48) - - Defining ABM (and why sales alignment is everything) (13:58) - - The “stop list”: ABM tactics they’ve killed (16:28) - - Why paid social “ABM awareness” is overrated (19:48) - - Shifting ABM to in-person and physical plays (23:58) - - Budgeting for ABM and how to start small (29:44) - - Why ABM measurement is different than traditional demand gen (35:04) - - How they build ABM audiences using data + signals (40:24) - - Scaling personalization without making it manual (46:04) - - 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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

#330 | Dave is joined by Ryan Narod, VP of Marketing at Rippling, to break down how Rippling has built one of the stand outbrands in B2B right now. Ryan walks through real examples of campaigns they’ve run over the last year, from scrappy iPhone videos and webinar promos to high-production customer stories and their 2026 Super Bowl commercial. They talk about how Rippling shifted from being great at growth marketing to building a brand people actually recognize, how they inject more personality and “human” into everything they ship, and how they measure brand marketing without losing pipeline accountability. To see Ryan's real campaign examples, head over to youtube.com/@heydavegerhardt.Timestamps(00:00) - - Why Rippling is going all-in on brand (02:48) - - Ryan’s background and why he joined Rippling (04:11) - - What Rippling does and how they position the platform (08:11) - - What “brand marketing” means at Rippling (10:31) - - Building a story that makes HR the hero (19:44) - - Ryan shares Rippling marketing examples (ads, videos, webinars) (28:02) - - High-production customer storytelling (Berries) (33:24) - - The “HR Deserves Better” campaign (36:22) - - How Rippling measures brand and pipeline impact (43:59) - - The Super Bowl commercial and what it takes to pull it off (46:02) - - 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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

#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 (03:01) - Jay’s virtual event business and the GURU acquisition (05:47) - Why you should stop calling it a “webinar” (07:42) - The “attend to receive” tactic to boost show rates (10:16) - Why on-demand is hurting your engagement (14:25) - Why Fridays and Sundays outperform for B2B email + webinars (17:58) - How to choose webinar topics based on your goal (18:25) - Why 22-minute webinars and shorter podcasts win (30:00) - The white space + no preview text email hack (38:12) - The “reply with GUIDE” tactic to boost engagement (39:58) - 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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

#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 (03:18) - – Canva’s marketing org structure (06:18) - – Blurring B2B and B2C (11:18) - – How Canva measures marketing impact (16:18) - – Turning free users into enterprise deals (21:18) - – Data science’s role in marketing (24:18) - – Balancing brand bets with ROI (31:44) - – Inside the “Love Your Work” campaign (38:44) - – How Canva executes large campaigns (42:44) - – Building enterprise credibility and trust (45:44) - – FedEx case study on brand governance (49:44) - – Lessons from Google and Meta (53:44) - – Why creativity is a marketing superpower (55:44) - – 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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

#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 (04:03) - What Esper does and why software powering hardware matters (06:48) - Why AI feels like the early internet shift (08:38) - Leading with curiosity instead of pretending to be an AI expert (11:18) - Why AI adoption is a behavior change problem, not a tools problem (13:18) - How Esper is rolling out AI with guardrails across the company (19:03) - Why “boring AI” that saves time matters most (20:18) - Phase 1 vs Phase 2 AI adoption in marketing teams (32:54) - AI, mentorship, and preparing the next generation of marketers (45:39) - Leadership advice for first-time CMOs and VPs (50:44) - 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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

#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 (03:41) - What Airops does and the AI search problem they’re solving (04:36) - What a “content engineer” actually is (16:16) - How to use AI without creating AI slop (19:32) - The 3 signals content is AI slop (35:08) - Why webinars are Airops’ best growth channel (37:33) - How they choose webinar topics and guests (53:45) - Other channels working (enablement, community, events) (56:45) - 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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 (05:11) - Meet the panel: marketing leaders from Webflow, EagleView, and Piedmont Global (08:49) - How AI search is changing buyer behavior vs traditional Google search (12:32) - EagleView’s real approach to AI search, greenfield opportunities, and prompt tracking (15:39) - What “black hat” vs “white hat” tactics look like in AI-driven search (19:46) - Webflow’s take: integrated marketing, generosity, and building useful tools (30:09) - Getting past high-level advice and into real execution (35:09) - “Circle the buyer”: how content builds demand before buyers are in-market (38:52) - Why PR is back: long-form press, citations, and brand credibility in AI search (45:52) - 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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 (04:58) - — The colonoscopy story. (12:18) - — Trojan Horse marketing. Get attention first. Sell later. Stop leading with your product. (17:18) - — Why you can’t create demand, only redirect it. (22:58) - — Category creation vs sub-categories. Most startups get this wrong. (25:48) - — Meaning-free brand assets. Why weird mascots and visuals actually work. (33:54) - — How to sell bold ideas internally without asking for permission. (37:44) - — Ads that look like ads fail. Attention is the job. (46:24) - — Triggers vs pain points. How people actually decide to buy. (51:44) - — 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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? (07:13) - — B2B Influencer pilot setup: why this channel, why now (14:31) - — The result: 45 demos, ~$1.1M pipeline, and how she tracked it (16:29) - — How to run influencers (21:54) - — Scaling idea: retainer-style influencer partnerships (26:36) - — Vector’s podcast: “awareness magnet” and the format that works (29:00) - — The production system: in-person batch recording a full season in 2 days (42:46) - — Jess’s LinkedIn strategy: why she started posting and what she optimizes for (54:34) - — 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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 (08:03) - – What “community” actually means (and what it definitely isn’t) (12:48) - – Why most B2B communities fail before they ever get traction (17:28) - – Community vs. content: what gets people in vs. what makes them stay (22:03) - – Why Slack groups aren’t a strategy (26:48) - – Treating community like a product, not a marketing channel (35:24) - – The role of trust, curation, and saying no to the wrong people (40:59) - – What community managers actually do behind the scenes (47:54) - – How in-person events changed the Exit Five community (54:04) - – 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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 (05:48) - – Meet Jess Lytle, Head of Marketing at Exit Five (08:02) - – How Jess got hired at Exit Five (webinar → DMs → job) (10:02) - – From demand gen to AI: early adoption, teaching, and Lovable (15:32) - – Why AI feels different than traditional martech (18:02) - – Content in 2026: originality, human insight, and AI distribution (29:52) - – NotebookLM: real marketing workflows and internal use cases (35:52) - – AI tools, team structure, and hybrid marketer roles (46:32) - – 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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 (04:02) - – Kieran’s career + the 2-year mission framework (09:32) - – The grind, early-career advice, and earning your stripes (12:02) - – Operator vs. manager + strong opinions in leadership (20:02) - – Why collaborative brainstorms fail (25:02) - – ChatGPT vs. Claude + how Kieran actually uses AI (33:52) - – Where AI is taking B2B marketing (answers → actions) (45:22) - – Picking a lane: technical vs. creative marketers (52:52) - – 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: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.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. Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/exitfive.Compound Growth Marketing - A full-funnel demand generation agency that helps high-growth cybersecurity, DevOps, and enterprise software companies drive more pipeline through AI SEO, paid media, and go-to-market engineering. Visit compoundgrowthmarketing.com and tell them Dave sent you.***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