The Dave Gerhardt Show (from Exit Five)

#343 | 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 t...

#342 | Recorded live at Exit Five's Marketing Leadership Retreat, this episode features Dave Kellogg sharing his framework for being the CMO everyone wants to work with. Dave draws on 12 years as a CMO across three companies, two CEO stints, and ten board seats to cover CMO failure archetypes, how to build a real partnership with your CRO, and why internal marketing is just as important as running marketing. Last time we had Dave on the podcast it was one of the most downloaded episodes of all-time, and this one is even better. Get your notebook read.

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#341 | In this Exit Five Live session, Cindy Dubon (Director of Growth Marketing, Goldcast), Kelly Arndt (Sr. Demand Gen Manager, Vector), Jeremy Chung (Founder and CEO, Ads by Jer), Tess Pfeifle (Associate Director of Marketing, AirVet), and Richard Meyer (Director of GTM and Growth, GoHappy) each break down a real ad campaign — the channel, the creative, the targeting, the spend, and the results. From influencer-led LinkedIn thought leader ads and CTV surround sound campaigns, to direct mail sequences, conference plays without a booth, and multi-channel signal-based targeting, these are campaigns you can actually steal from. Co-hosted by Jess Cook, VP Ma...

#340 | Dave sits down with Kipp Bodnar, CMO of HubSpot, to talk about the journey from running a company blog to leading marketing at a $2B business. Kipp started at HubSpot in 2010 when it was doing $10M in revenue and grew the blog from 200k to 1M monthly uniques before taking on more and more of the marketing function. They get into how to set big goals and work backwards from them, how to move fast without losing focus, and the mindset shift that separates individual contributors from marketing leaders. 

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#339 | Dave is joined by Brandon Redlinger, former VP of Marketing and co-founder of The Forge, for a conversation about how to build an ABM program that works. They cover how to know if your company is ready for ABM, how to select and score target accounts, and why most teams fail by spreading themselves across too many accounts too fast. Brandon also shares the plays that generate real pipeline, how to think about measurement without overcomplicating it, and why ABM and demand gen shouldn't be two separate functions.

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Dave is joined by Davang Shah, VP of Marketing at LinkedIn, for a conversation about what actually works with LinkedIn ads right now. They cover why brand and performance aren't two separate strategies, how to think about measurement beyond last-click attribution, and why 95% of your buyers aren't in market at any given time. Davang also shares the data behind thought leader ads, what most marketers get wrong about the buyer journey, and how he's leading his own team through the AI shift.

Timestamps

#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.<...

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...

#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...

#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 bu...

#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.

#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, t...

#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 with...

#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 s...

#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

#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.

#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 unlo...

#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 wh...

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...

#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 th...

#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.

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#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

#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

#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

#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

#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

#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 Linked...

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

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 ne...

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...

#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

#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...

#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

#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 wher...

#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/driv...

#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 exi...

#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.

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#306 Executive Insights | This episode was recorded live at our annual event, Drive 2025. I hosted Sylvia LePoidevin (CMO, Kandji), Trinity Nguyen (CMO, UserGems), and Natalie Taylor (Head of Marketing, Capsule) for a leadership panel breaking down what’s working in B2B marketing. They get into events that reliably create pipeline, outbound that still converts, media plays LLMs keep citing, and the tactics they’ve stopped running (like generic webinars that no one shows up for).

Want to come to Drive next year? Head over to exitfive.com/drive to join the waitlist for Drive 2026 and be the firs...

#305 Influencer Marketing | This episode is a live session from Drive 2025 with Brianna Doe, where she breaks down why influence is now shaping every step of the buying journey, how smart B2B brands are borrowing plays from B2C, and what it really takes to build a creator program that doesn’t flame out on day one. She gets into the messy reality of picking the right creators and measuring impact without deluding yourself with vanity numbers.

Head over to exitfive.com/drive to join the waitlist for Drive 2026 and be the first to know when tickets go...

#304 | AI Buying Shift | This episode is from a recent Exit Five live session where I pulled together Lindsay O'Brien (Head of Marketing & Operations, Predictiv), Tom Wentworth (CMO, incident.io), and Aditya Vempaty (VP of Marketing, MoEngage) for a real talk on how AI is completely rewiring the B2B buying journey. We got into why buyers no longer need your pretty funnel, how AI-powered research changes the sales call, and what that means for your GTM strategy.

Timestamps