#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 should approach demand generation and brand building. In this conversation, Dave and Gurdeep dive deep into why marketing is ultimately a game of memo...
Sep 08, 2025•53 min•Ep. 280
#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. Dave and Holly cover: Why video hits differently in B2B and how to make yours stand out without blowing your budget How AI is reshaping the content pro...
Sep 04, 2025•1 hr 2 min•Ep. 279
#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: Jillian Hoefer’s “content concierge” GPT trained on proprietary research to surface stats, quotes, and data for blogs, sales decks, and thought leadership...
Sep 01, 2025•1 hr 2 min•Ep. 278
#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 Kristine cover: How Canva balances brand-building with pipeline accountability, and why they view brand investment as long-term growth. The playbook C...
Aug 28, 2025•53 min•Ep. 277
#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 bringing that experience into the fast-changing world of AI. Dave and Kady cover: How to evolve as a CMO across industries, personas, and business mod...
Aug 25, 2025•55 min•Ep. 276
#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 cover: Why LinkedIn is still the best channel for founders to build authority, attract talent, and connect with customers How to turn everyday founder c...
Aug 21, 2025•48 min•Ep. 275
#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 alignment between sales, marketing, and ops Why early-stage companies must align operational complexity with their growth maturity How continuous planning h...
Aug 18, 2025•56 min•Ep. 274
#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 cover: How to build a recognition strategy that actually improves retention (without needing a big budget or fancy platform) Why employee motivation d...
Aug 14, 2025•58 min•Ep. 273
#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 keynote, a boardroom pitch, or a weekly team update. Matt and Vincent cover: The 4-part framework behind talks that stick: Tension, Trust, Teaching, Take...
Aug 11, 2025•53 min•Ep. 272
#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 RevOps and GTM engineering (and why the latter is more focused on building than just integrating) Real GTM engineering use cases, from AI-powered sa...
Aug 07, 2025•59 min•Ep. 271
#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 reach modern B2B buyers. Dave and Holly cover: The 4 channels her lean team is betting on to drive enterprise pipeline (and what’s not working anymor...
Aug 04, 2025•46 min•Ep. 270
#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 volume is now a top indicator of visibility in AI-generated results (and how to grow it) The new playbook for SEO in 2025, including what metrics...
Jul 31, 2025•56 min•Ep. 269
#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 followers and partnerships with tools like Semrush. Matt and Sara cover: What it really looks like to run full-stack B2B marketing without a team How t...
Jul 28, 2025•48 min•Ep. 268
#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 Jennifer cover: How product marketing can become a company-wide growth lever through tighter GTM alignment, strategic planning, and better customer ...
Jul 24, 2025•53 min•Ep. 267
#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. Jess and Matt cover: How content marketers can transition into marketing leadership and what gaps to prepare for The strategy behind building a brand t...
Jul 21, 2025•58 min•Ep. 266
#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 inside Exit Five to support others facing the same challenges. Matt and Sandra cover: How non-SaaS teams drive growth without demos, PLG, or huge lea...
Jul 17, 2025•54 min•Ep. 265
#264 Async Work | In this episode, Dave is joined by Ashley Faus , Director of Lifecycle Marketing at Atlassian, and Dr. Molly Sands , Head of the Teamwork Lab at Atlassian. Ashley brings deep experience in cross-functional B2B marketing leadership, while Molly leads a team of behavioral scientists designing better ways for teams to collaborate. Together, they unpack how Atlassian has rethought marketing org structure, internal comms, and meetings to drive higher output with fewer syncs. Dave, A...
Jul 14, 2025•58 min•Ep. 264
#263 Marketing Strategy | Dave is joined by Jason Lyman , CMO at Customer.io, a customer engagement platform used by over 7,500 companies. Jason has led marketing at Dropbox, BetterCloud, and now heads a 30-person team driving growth across both PLG and sales-led motions. Dave and Jason cover: How to structure a B2B marketing org for scale, alignment, and channel ownership Why events are their #1 channel and how creative formats drive real pipeline The KPI + OKR system they use to prioritize wor...
Jul 10, 2025•45 min•Ep. 263
#262 Content Strategy | Dave sits down with Chelsea Castle , Head of Content and Brand at Close. Chelsea talks about her experience in B2B SaaS and shares how to build impactful content that resonates with your audience. Chelsea and Dave cover: How leveraging internal and cross-functional knowledge can create a content goldmine Why it is important to repurpose podcast episodes, webinars, and other media into multiple forms of content to maximize their value Strategies for integrating SEO with au...
Jul 07, 2025•54 min•Ep. 262
#261 AI & Creativity | In this episode, Dave is joined by Mark Schaefer , marketing strategist, keynote speaker, and author of 11 books, including his latest, Audacious: How Humans Win in an AI Marketing World . Mark has spent decades studying the intersection of marketing, tech, and human behavior, and his ideas have helped reshape how B2B brands think about relevance, creativity, and differentiation in a noisy digital world. Dave and Mark cover: Why playing it safe is the biggest threat to...
Jul 03, 2025•55 min•Ep. 261
#260 Product Marketing | Dave is joined by Matt De Vincentis , VP of Product Marketing at Atlassian. With a background that spans engineering, product marketing, and leadership at companies like VMware and Palo Alto Networks, Matt shares how Atlassian structures its product marketing team, prioritizes work, and stays tied to business outcomes, even at massive scale. Dave and Matt cover: How Atlassian connects product marketing to revenue and pipeline (and why PMMs need to “own the outcome”) How ...
Jun 30, 2025•55 min•Ep. 260
#259 Paid Ads | In this episode, Dave is joined by Pranav Piyush , founder and CEO of Paramark, a platform helping B2B marketers run real experiments to measure ad performance. Pranav brings a sharp point of view on attribution, channel performance, and how to actually prove what’s working across your paid media mix. Dave and Pranav cover: Real-world results from 7 B2B ad campaigns, including branded search, YouTube, billboards, and Performance Max Why most marketers are misusing the word “test”...
Jun 26, 2025•55 min•Ep. 259
Dave here. Interrupting the regular podcast feed for a 3 minute story and rant about why I love the job of marketing and what it might mean in a world where AI is advancing so rapidly and changing the role of marketing. Send guest pitches and ideas to hi@exitfive.com Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter Check out the Exit Five job board: https://jobs.exitfive.com/ Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership *** This ...
Jun 24, 2025•5 min•Ep. 258
#257 AI Strategy | Dave is joined by Kieran Flanagan , SVP of Marketing at HubSpot and former CMO at Zapier. Kieran is a rare blend of technical operator, creative strategist, and team builder. He’s spent his career pushing the edges of B2B marketing, most recently through his work leading AI transformation initiatives at scale. Dave and Kieran cover: How AI is reshaping B2B marketing workflows, content creation, and team structure Why the best marketers will specialize at the “outer edges” of c...
Jun 23, 2025•57 min•Ep. 257
#256 Email Deliverability | In this episode, Dan is joined by Sarah McNamara , Revenue Operations & GTM Strategy Lead at Vector, and Alex Fine , co-founder of Understory, an agency helping B2B SaaS companies scale with outbound, paid, and email. Both Sarah and Alex are experts in email strategy, specifically the behind-the-scenes mechanics that make or break your deliverability. They break down what B2B marketers often overlook when it comes to getting emails opened, read, and replied to, an...
Jun 19, 2025•56 min•Ep. 256
#255 Leadership | In this episode, Dave is joined by Kelly Hopping , CMO of Demandbase, a B2B company known for pioneering account-based marketing. Kelly leads a 70+ person marketing org that spans brand, demand gen, product marketing, events, and SDRs, and she shares exactly how she structures and operates that team to drive results. Dave and Kelly cover: How to design and run a full-funnel marketing team that includes SDRs, content, field, and brand, and keep them aligned on pipeline The annua...
Jun 16, 2025•51 min•Ep. 255
#254 Brand | In this episode, Dave sits down with Kira Federer , VP of SMB Marketing at Paramount Advertising, and formerly at companies like Reddit and Glassdoor. Kira shares her journey from sales to product marketing and the lessons she’s learned along the way. Dave and Kira discuss: How to align marketing and sales through co-creation to ensure your sales team uses the content you create The value of a strong messaging framework and how it drives consistency in B2B marketing Why you need to ...
Jun 12, 2025•44 min•Ep. 254
#253 Lifecycle Marketing | In this episode, we’re joined by two expert lifecycle marketers: Charlotte Hardin , Lifecycle Marketing Manager at Rebuy Engine, and Naomi West , Senior Product Manager at Customer.io . Charlotte and Naomi bring years of hands-on experience running email, onboarding, and retention programs inside B2B SaaS companies. They break down how B2B teams can use lifecycle marketing to drive more revenue, boost product engagement, and strengthen customer relationships, without n...
Jun 09, 2025•53 min•Ep. 253
#252 Category Creation | Dave is joined by Josh Lowman , Founder and Creative Director of Gold Front, a category design studio that’s worked with brands like Uber, Notion, and Qualtrics. Josh is a leading voice in strategic brand positioning and category creation. He’s spent over a decade helping high-growth B2B companies define what makes them irreplaceable in crowded markets. Dave and Josh cover: Why most category creation efforts fail (and what to do instead) The four real paths to category l...
Jun 05, 2025•1 hr 1 min•Ep. 252
#251 Website Optimization | In this episode, Danielle is joined by Guy Yalif , Chief Evangelist at Webflow; Talia Wolf , Founder and CEO of Getuplift; and Scott Cappuzzo , Web Strategist at Webflow. Together, they dig into what actually makes a B2B website convert and why most homepages are missing the mark. This panel brings deep experience in conversion rate optimization, UX strategy, and messaging clarity, sharing practical tips and live feedback from real B2B websites submitted by Exit Five ...
Jun 02, 2025•1 hr 2 min•Ep. 251
