The Exit Five CMO Podcast (Hosted by Dave Gerhardt)

Dave Gerhardt
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Dave Gerhardt (Founder of Exit Five, former CMO) chats with top marketing leaders and CMOs. Join 5,000+ members in our private community at exitfive.com.

  1. 8 HR AGO

    Why Cookie Cutter Marketing Doesn’t Work with Gurdeep Dhillon, CMO at ContentStack

    #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 memory and reputation, not just lead generation. Dave and Gurdeep cover: The role of Demand Gen in 2025 (and what's changed)Why Brand and Reputation should be prioritized over Lead GenerationProven strategies to create urgency and close sales deals in enterprise marketsA glimpse into ContentStack’s team structure and how they plan for growthTimestamps (00:00) - - Intro to Gurdeep (06:51) - - Brand and Audience Marketing (08:03) - - How the Role of Demand Gen is Changing (12:13) - - Brand and Reputation > Lead Generation (17:03) - - How Contentstack is Doing Demand Gen (19:41) - - How to Create Urgency to Win Sales Deals (21:22) - - Making a Good Offer in B2B Marketing (22:38) - - Why Being Bold and Taking Risks is Important in Marketing (28:57) - - Selling Your Vision to Leadership (31:38) - - How Contentstack Has Over 10,000 Global ICP Accounts (36:21) - - Team Structure at Contentstack (41:19) - - Running Marketing and Operating a High-Performing Team (43:35) - - Setting Effective Annual Plans (45:50) - - AI’s Role in Marketing (49:24) - - Closing Thoughts Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership *** This episode of the Exit Five podcast is brought to you by Qualified. AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine. That’s where Qualifed comes in with Piper, their AI SDR agent. Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound? Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline. The Agentic Marketing era has arrived. And if you’re a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help. Hire Piper, the #1 AI SDR Agent, and grow your pipeline today. You can learn more at qualified.com/exit5

    53 min

  2. 4 DAYS AGO

    The Unfiltered Truth About Video Marketing and AI with Holly Xiao and Dave Gerhardt

    #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 budgetHow AI is reshaping the content production cycle and freeing up marketers to focus on storytellingWhy early adoption matters, and how small teams can use AI to punch above their weightYou can expect a candid, practical conversation about how to scale content, stay relevant, and make the most of AI. Timestamps (00:00) - – Intro (01:27) - – Why this conversation matters (02:44) - – AI is making marketing exciting again (03:53) - – Dave’s early bet on video (05:53) - – How LinkedIn video exploded (07:10) - – ROI vs. brand building (08:25) - – From connection to conversion (10:10) - – Why video feels more human (12:16) - – “Maybe your videos suck” (14:22) - – The problem with corporate videos (16:10) - – The value of repetition and reps (18:34) - – How AI speeds up content cycles (20:51) - – Real AI tools Dave is using (22:28) - – Decks, data, and automation (24:53) - – Why creativity still wins (27:15) - – The return of the creative CMO (31:14) - – Personalized content at scale (33:13) - – AI vs. in-person experiences (35:55) - – Do audiences care if it’s AI? (38:41) - – What makes an AI video work (41:18) - – Using AI to test and scale video (43:59) - – What small teams should do first (47:37) - – Final advice: be an early adopter Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership *** This episode of the Exit Five podcast is brought to you by Qualified. AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine. That’s where Qualifed comes in with Piper, their AI SDR agent. Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound? Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline. The Agentic Marketing era has arrived. And if you’re a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help. Hire Piper, the #1 AI SDR Agent, and grow your pipeline today. You can learn more at qualified.com/exit5

    1h 2m

  3. 1 SEPT

    How B2B Marketers Are Actually Using AI for Content

    #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 leadershipJake Heap’s workflow using Meshy + VEO 3 to turn a simple mascot into animated 3D brand characters in minutesJessica Lytle’s no-code ROI calculator built in Lovable that sales reps now run live on calls to build business casesUgi Djuric’s high-volume content engine that scrapes industry news and sales call transcripts, then uses AI to summarize, generate content ideas, and even score leadsAnton Ruis’ AI-powered buyer brief builder that pulls real-time economic data and tailors sales messaging to specific personasIt’s part workshop, part competition, and packed with creative, tactical ways to put AI to work in B2B marketing today. Timestamps (00:00) - – Dave kicks off in a tux (02:44) - – Record-breaking registrations (03:22) - – Meet the judges: Benny & Jess (08:10) - – Jillian’s “victim of repurposing” intro (08:50) - – Building a “content concierge” GPT from research data (10:14) - – Injecting stats + quotes into blogs and decks (14:10) - – How one report fueled 9+ months of content (19:10) - – Jake on bringing AI into marketing ops (20:33) - – Turning a mascot into a 3D character with Meshy (21:18) - – Animating it in VEO 3 (no designer needed) (24:33) - – Cutting animation time from weeks to minutes (30:32) - – Jessica builds a no-code ROI calculator in Lovable (33:41) - – AEs use it live on sales calls (34:25) - – Adding benchmarks + transparency to ROI math (41:43) - – Ugi’s AI engine scrapes + summarizes industry news (44:00) - – Training custom GPTs on expert insights (50:40) - – Anton’s real-time buyer briefs from economic data (53:15) - – Tailoring briefs for CROs, enablement, PMMs (56:59) - – Judges crown the winning use case + Dave’s wrap-up Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership *** This episode of the Exit Five podcast is brought to you by Qualified. AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine. That’s where Qualifed comes in with Piper, their AI SDR agent. Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound? Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline. The Agentic Marketing era has arrived. And if you’re a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help. Hire Piper, the #1 AI SDR Agent, and grow your pipeline today. You can learn more at qualified.com/exit5

    1h 2m

  4. 28 AUG

    The Strategy Behind Canva’s B2B Growth with Emma Robinson and Kristine Segrist

    #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 Canva uses to turn bottom-up adoption into enterprise deals, including how product signals guide upsell and expansion.How their team structure, data science investments, and creative bets (like the Love Your Work campaign) work together to scale B2B marketing without losing Canva’s approachable brand identity.This episode offers a practical look at how one of the world’s most recognizable platforms approaches B2B growth. Timestamps (00:00) - – Intro (03:09) - – Canva’s marketing org structure (06:09) - – Blurring B2B and B2C (11:09) - – How Canva measures marketing impact (16:09) - – Turning free users into enterprise deals (21:09) - – Data science’s role in marketing (24:09) - – Balancing brand bets with ROI (30:54) - – Inside the “Love Your Work” campaign (37:54) - – How Canva executes large campaigns (41:54) - – Building enterprise credibility and trust (44:54) - – FedEx case study on brand governance (48:54) - – Lessons from Google and Meta (52:54) - – Why creativity is a marketing superpower (54:54) - – Closing thoughts Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership *** This episode of the Exit Five podcast is brought to you by Qualified. AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine. That’s where Qualifed comes in with Piper, their AI SDR agent. Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound? Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline. The Agentic Marketing era has arrived. And if you’re a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help. Hire Piper, the #1 AI SDR Agent, and grow your pipeline today. You can learn more at qualified.com/exit5

    53 min

  5. 25 AUG

    How to Evolve as a CMO: Navigating New Markets, Personas, and Business Models with Kady Srinivasan

    #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 modelsThe three core systems CMOs need to scale teams and drive alignmentHow AI is reshaping marketing roles, workflows, and the skills future CMOs will needYou’ll walk away with lessons you can apply to your own career, no matter what market or role you’re in. Timestamps (00:00) - – Intro (02:24) - – From engineer to reluctant marketer (04:58) - – Gaming years and “coolest mom” cred (07:13) - – The story behind You.com’s domain (08:52) - – Why she jumped into AI (11:21) - – Reinventing yourself as a CMO (13:21) - – Fundamentals that never change in marketing (15:34) - – Aligning marketing with company strategy (18:45) - – Pivoting the ICP at Lightspeed (21:47) - – Lessons on cross-functional alignment (24:29) - – Letting go to grow as a leader (27:14) - – Systems every CMO should set up (34:14) - – Why no single playbook works (35:55) - – How AI is reshaping marketing roles (50:35) - – Building an AI-first marketing org and closing thoughts Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership *** This episode of the Exit Five podcast is brought to you by Qualified. AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine. That’s where Qualifed comes in with Piper, their AI SDR agent. Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound? Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline. The Agentic Marketing era has arrived. And if you’re a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help. Hire Piper, the #1 AI SDR Agent, and grow your pipeline today. You can learn more at qualified.com/exit5

    55 min

  6. 21 AUG

    Why Every Founder Needs a LinkedIn Strategy with Brad Zomick

    #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 customersHow to turn everyday founder communications into high-impact LinkedIn contentThe unexpected ROI of founder-led content, from recruiting and partnerships to real-time message testingIf you’ve been wondering how to turn LinkedIn into a real growth engine for your brand, this episode is your blueprint. Timestamps (00:00) - – Intro (03:09) - – Early days of LinkedIn (08:39) - – Building Drift with founder brand (14:39) - – Why every founder needs LinkedIn (18:39) - – The hidden ROI of posting (27:24) - – Dave’s personal posting system (30:54) - – How to never run out of content (34:54) - – Unexpected benefits of being visible (39:24) - – Is it too late to start? (42:24) - – Who inspires Dave today (44:39) - – What’s next for Exit Five (46:24) - – Closing thoughts Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership *** This episode of the Exit Five podcast is brought to you by Qualified. AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine. That’s where Qualifed comes in with Piper, their AI SDR agent. Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound? Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline. The Agentic Marketing era has arrived. And if you’re a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help. Hire Piper, the #1 AI SDR Agent, and grow your pipeline today. You can learn more at qualified.com/exit5

    48 min

  7. 18 AUG

    Why Marketers Need Great RevOps Partners with Sean Lane, Founding Partner at BeaconGTM and RevOps Expert

    #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 opsWhy early-stage companies must align operational complexity with their growth maturityHow continuous planning helps marketing and ops teams stay agile as business challenges come upTimestamps (00:00) - - Intro to Sean (06:32) - - Going From Founder Led Sales to Having A Professional GTM (09:13) - - How Ops Bridges Business Goals (13:03) - - How To Align Sales, Marketing, and Operations (17:12) - - Why You Need A Clear Marketing Strategy (19:38) - - How To Build A Partnership Between Marketing and Operations (26:02) - - Guidelines for long term vs short term budgeting and planning (31:50) - - Marketing’s Role At The Bottom Of The Funnel (36:45) - - How To Get “Hand-raisers” For Your Product In The Customer Journey (40:37) - - Do Engaged Accounts Measure The Success Of Marketing? (42:27) - - Sean’s Podcast ROI (44:43) - - AI Use Cases In Ops (49:45) - - How To Hire A Good Ops Person (53:13) - - Closing Remarks Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership *** This episode of the Exit Five podcast is brought to you by Qualified. AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine. That’s where Qualifed comes in with Piper, their AI SDR agent. Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound? Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline. The Agentic Marketing era has arrived. And if you’re a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help. Hire Piper, the #1 AI SDR Agent, and grow your pipeline today. You can learn more at qualified.com/exit5

    56 min

  8. 14 AUG

    Leading Through Change: Recognition, Retention & Culture for Marketing Teams with Rachel Weeks

    #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 dips during times of stress, layoffs, or AI disruption and what great leaders do differentlyThe role of marketing in internal culture: from branding the program to building peer-driven engagementWhether you’re managing a small team or leading an entire department, this episode is packed with practical insights to help you build a culture where marketers feel valued, motivated, and ready to stay. Timestamps (00:00) - – Intro (03:09) - – Rachel’s background and leadership lens (05:39) - – What actually makes a recognition program work (08:09) - – How marketing supports internal culture building (11:09) - – Recognition during org changes, stress, and funding rounds (14:09) - – The impact of AI on morale and motivation (17:39) - – What happens when recognition disappears (19:39) - – The “10 minutes by Friday” habit (22:09) - – Easy, no-budget ways to recognize team members (25:09) - – Performance-driven vs. values-driven recognition (30:24) - – Monetary vs. non-monetary rewards (and what people really want) (33:54) - – Recognition vs. pay raises: what the data says (37:54) - – Why people leave even when they’re paid well (41:54) - – How to ask for (and give) better feedback (46:54) - – Using AI to create space for strategic work (53:54) - – Final thoughts on leadership, retention, and culture Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck out the Exit Five job board: https://jobs.exitfive.com/Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership *** This episode of the Exit Five podcast is brought to you by Qualified. AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine. That’s where Qualifed comes in with Piper, their AI SDR agent. Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound? Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline. The Agentic Marketing era has arrived. And if you’re a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help. Hire Piper, the #1 AI SDR Agent, and grow your pipeline today. You can learn more at qualified.com/exit5

    58 min
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Dave Gerhardt (Founder of Exit Five, former CMO) chats with top marketing leaders and CMOs. Join 5,000+ members in our private community at exitfive.com.

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