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-marke…

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 …

#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…

#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 w…

#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 (…

#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 …

#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-…

#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 s…

#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 bui…

#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 st…

#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…

#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 …

#303 Storytelling | This episode is from Drive 2025, our 2-day in-person event for B2B marketers in Burlington, VT. Harry Dry, creator of Marketing Examples and one of the best copywriters on the internet, shared a masterclass on storytelling, creativity, and writing marketing that actually connects—showing how to find great ideas, turn real storie…

#302 Growth | Dave is joined by Priscilla Barolo, former head of comms at Zoom (for nearly 10 years, including the pandemic) and current VP of Marketing at Neat, an Oslo-based video tech company. Neat’s tech is used around the world from major enterprises like Atlassian to the White House. With a decade-long career at Zoom, including during its hyp…

#310 Leadership & Strategy | I sat down with Maura Rivera, CMO at Qualified, to talk about what it’s like leading marketing at one company for six years (and why most of her team has been there just as long). We got into how product launches are the glue that hold their marketing together, what agentic marketing really means for the future, why out…

#300 Drive | This episode is from Drive 2025, our 2-day in-person event for B2B marketers in Burlington, VT. It features Diane Wiredu, Founder of Lion Words and expert in B2B messaging and positioning. She shared a killer talk on “What Your Messaging Is Missing,” breaking down why most B2B copy sounds the same and how to close the meaning gap by fo…

#299 Drive | This episode is from Drive 2025, our 2 day in-person event for B2B marketers in Burlington, VT. Our first speaker was Sangram Vajre, Co-founder and CEO of GTM Partners and expert in GTM strategy. He shared a great session on building a repeatable GTM Operating System for sustainable growth, offering insight from 100 companies on what s…

#298 Q&A | OK I asked my team for some questions; a bit of a mailbag type of episode. So I sat down solo for this one and answered 15 questions from the Exit Five team about work, life, marketing, and everything in between. We got into everything from my daily routine and how I think about LinkedIn, to the best career advice I’ve ever gotten, what …

#297 Leadership | I sat down with Kelly Cheng, CMO at Goldcast, to talk about her path from growth marketer to marketing leader, how she’s built and scaled Goldcast’s marketing org, the shift from PLG to sales-led, and why she believes great CMOs play the long game. Timestamps (00:00) - – Intro (03:08) - – Kelly’s path from Hong Kong to Boston (06:…

Hey it's me live from the airport, LGA to be exact. Sorry for the poor audio, my AirPods make it way worse than just talking into the phone, now I know. But we cleaned it up a bit. Recapping our NYC event if you missed it, talking about the ROI of hanging out in person and what's next. Join 50,0000 people who get our Exit Five Newsletter here: http…

#295 Messaging | Dave is joined by Emma Stratton, founder of Punchy, where she helps B2B tech companies sharpen their positioning and write messaging that actually connects. Emma’s worked with hundreds of teams to cut through vague, abstract copy and turn it into language buyers instantly get. Dave and Emma cover: How to go from vague to punchy usi…

#294 Event Strategy | First time podcast guest alert! I invited Allison and Anna from the Exit Five team on for a conversation post Drive 2025 - to talk about lessons learned and behind the scenes from our annual marketing conference in Vermont. Snag your tickets for next year now exitfive.com/drive Timestamps (00:00) - – Intro (02:08) - – Why even…

#293 Email Marketing | I'm trying to make my way from Vermont to New York and back with a mini episode talking about email (is email dead?), direct mail, the Dream 100, and a smart lesson from a non-B2B marketer. Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletter Learn more about Exit Five's private marke…

#291 In-Person Events | I decided to break the pattern with a solo podcast, just me and my phone, walking around the woods at my home in Vermont on a damp October morning before heading to NYC for the Exit Five meetup. I talk about my goals for the week, our plans, why we're hosting a dinner, the value of meeting in-person, remote vs. in office wor…

#290 AI Workflows | In this episode, Dave is joined by Dan Guenet, GTM Engineer at Compound Growth Marketing, and Eoin Clancy, Head of Growth at AirOps. Both guests are at the forefront of building AI workflows that make marketing more efficient and scalable, from content creation to sales enablement. Dave, Dan, and Eoin cover: How to use Clay, Zap…

#289 Strategy | Dave is joined by Sydney Sloan, Chief Marketing Officer at G2, where she’s leading the charge on integrating AI into marketing, rethinking team structures, and modernizing how B2B brands build trust. Sydney brings decades of experience from companies like Adobe, Alfresco, and Salesloft, and now oversees one of the largest software m…

#288 AI in Marketing | In this episode, Dave is joined by three B2B marketing leaders: Sara Ajemian, Head of Brand & Communications at SOCi, Jennifer Delevante-Moulen, CMO at Knak, and Tara Robertson, CMO at Bitly. Together they share real-world perspectives on how AI is actually shaping marketing teams today—what’s working, what’s not, and how lea…

#287 Brand Marketing | In this episode, Matt is joined by Amrita Gurney, a veteran B2B marketing leader who has scaled some of Canada’s fastest-growing startups and now works as a fractional CMO. At Float, she led bold offline campaigns, from billboards and buses to TV spots, that helped the company stand out against major banks and build lasting b…

#286 Growth | In this episode, Dave is joined by Kevin White, Head of Marketing at Common Room, a leading customer intelligence platform for go-to-market teams. Kevin shares insights from his experience helping teams capture and act on digital breadcrumbs to optimize their marketing and sales efforts. Dave and Kevin cover: How to be a good marketer…

#285 Creative Strategy | In this episode, Dave is joined by Pranav Piyush, Founder & CEO of Paramark, a measurement platform helping B2B and B2C companies run smarter marketing experiments. Pranav is known for turning strategy documents into repeatable creative processes that generate campaigns, ads, and content tied directly to a company’s story. …

#284 Brand | Dave sits down with Ari Yablok, Head of Brand at Island, to share his approach to creating a brand in the cybersecurity space. Ari shares his journey from agency life to leading the brand narrative at Island, where he helped build the concept of the "enterprise browser." Dave and Ari Cover: The key differences between category creation…

#283 Marketing Leadership | In this episode, Dave is joined by Sylvia Lepoidevin, CMO of Kandji, a leading platform for managing and securing Apple devices in the workplace. Sylvia shares her journey from employee #4 to CMO at Kandji, driving the company’s growth to a $850M valuation. She talks about her experience building efficient marketing team…

#282 CRO | Matt is joined by Haley Carpenter, founder of Chirpy, a conversion rate optimization agency. Haley has nearly a decade of CRO experience across agency, SaaS, and eCommerce, and she’s known for helping brands use research and testing to make smarter marketing decisions. Matt and Haley cover: Why CRO isn’t just A/B testing, and how researc…

#281 Growth | In this episode, Dave is joined by Chris Walker, CEO of Passetto, and a prominent voice on LinkedIn, where he has been pushing the boundaries of B2B marketing for years. Chris shares actionable insights and tactics on social media strategy, what has changed in marketing over the last five years, and how to build effective feedback loo…

#280 Strategy | In this episode, Dave is joined by Gurdeep Dhillon, CMO of Contentstack. Gurdeep has built an impressive career leading marketing at some of the biggest names in enterprise software, from SAP to Adobe, Marketo to Zoura. Now at Content Stack, he's challenging conventional B2B marketing wisdom in rethinking how enterprise companies sh…

#279 Content Strategy | In this episode, Dave joins Holly Xiao from HeyGen for an unfiltered conversation about where AI and video marketing are headed. Holly leads B2B marketing at HeyGen, an AI-powered video platform, and she sat down with Dave to dig into what’s working (and what’s not) when it comes to creating content that actually connects. T…

#278 Content | In this episode, Dave brings together five B2B marketers who aren’t just talking about AI, they’re actually using it to change how their teams work. Each finalist from the Exit Five x Walnut AI Sessions takes the (virtual) stage to demo their workflow, share results, and answer questions from the judges. Here’s what you’ll hear: Jill…

#277 Growth | Dave is joined by Emma Robinson, Head of B2B Marketing at Canva, and Kristine Segrist, VP of Consumer Marketing at Canva. Together, Emma and Kristine lead the teams driving Canva’s growth across both enterprise and consumer audiences, helping the company scale into a platform now used by over 95% of the Fortune 500. Dave, Emma, and Kr…

#276 Career Growth | Dave is joined by Kady Srinivasan, CMO at You.com, an AI-first company building infrastructure for enterprise agents. Kady has led marketing at some of the world’s most recognizable companies, including Dropbox, Klaviyo, and Lightspeed, where she scaled teams, drove massive revenue growth, and navigated ICP pivots. Now, she’s b…

#275 LinkedIn Strategy | In this episode, Dave is joined by Brad Zomick, a B2B marketing consultant and host who has helped founders and executives build their presence on LinkedIn. Together they break down why a strong LinkedIn strategy is no longer optional for founders, it’s one of the most effective growth levers in B2B today. Dave and Brad cov…

#274 Growth | In this episode, Dave is joined by Sean Lane, Founding Partner at BeaconGTM and RevOps expert, to talk about scaling RevOps in B2B. With over a decade of experience at Drift and other B2B SaaS companies, Sean shares actionable tips for marketers looking to align operations with business goals. Dave and Sean cover: How to build alignme…

#273 Leadership | Matt is joined by Rachel Weeks, a veteran B2B marketing leader with over 20 years of experience guiding companies through acquisitions, layoffs, and tech disruption. Rachel has led both corporate and field marketing teams and is passionate about recognition-driven team cultures that retain and empower top talent. Matt and Rachel c…

#272 Presentation Skills | Matt is joined by Vincent Pierri, a speaking coach who helps executives and marketers craft compelling, high-stakes talks. With a background as a pastor and public communicator, Vincent has developed a repeatable framework that helps B2B marketers improve how they show up in front of a room, whether it’s a conference keyn…

#271 GTM Engineering | In this episode, Dave is joined by John Short, CEO of Compound Growth Marketing, along with Cammy Keiler, Justin Johnson, and Dan Guenet. Together, they break down the rise of GTM engineering, what it is, how it differs from RevOps, and why B2B teams are investing in it. Dave and the crew cover: The core difference between Re…

#270 Strategy | Dave is joined by Holly Xiao, Head of B2B Marketing at HeyGen, an AI video generation platform that helps teams produce personalized, high-quality content, fast. Holly has led marketing at high-growth startups and now runs the enterprise GTM motion at HeyGen, where she blends strategy, creative execution, and AI-powered workflows to…

#269 AI Search & SEO | In this episode, Dave is joined by Andrei Țiț, Head of Product Marketing at Ahrefs, a leading SEO tool trusted by marketers around the world. Andrei has been on the front lines of how AI is reshaping search and what that means for marketers trying to stay visible in an AI-first world. Dave and Andrei cover: Why branded search…

#268 Solo Marketing | In this episode, Matt is joined by Sara Lattanzio, Head of Marketing at Stryber, a venture-building consultancy that helps corporates launch new startups. Sara runs the entire marketing function solo, from strategy and content to outbound and brand, and has built a powerful personal brand along the way with 40,000+ LinkedIn fo…

#267 Product Marketing | Matt is joined by Jennifer Cannizzaro, VP of Product Marketing at Responsive and former marketing leader at Whoop and DocuSign. Jennifer brings deep experience in building strategic, insight-driven marketing teams at high-growth B2B companies and she’s at the forefront of using AI to scale smarter, not just faster. Matt and…

#266 Marketing Leadership | In this episode, Matt is joined by Jess Cook, Head of Marketing at Vector, a platform pioneering the contact-based marketing category. Jess has spent her career building standout content strategies at B2B brands like LASSO and Fastly, and she recently made the jump from Head of Content to first-time Head of Marketing. Je…

#265 Non-SaaS Marketing | In this episode, Matt sits down with Sandra Rand, a fractional head of marketing who works with early-stage, non-SaaS B2B companies. She’s led marketing for PE-backed, self-funded, and services-based businesses, where big budgets and SaaS-style playbooks aren’t the norm. She’s also building the Non-SaaS Marketers subgroup …