The Exit Five Podcast

Latest Episodes:

The Strategy Behind Canva’s B2B Growth with Emma Robinson and Kristine Segrist Feb 12, 2026

Show notes

#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
(02:00) - – Canva’s marketing org structure
(05:00) - – Blurring B2B and B2C
(10:00) - – How Canva measures marketing impact
(15:00) - – Turning free users into enterprise deals
(20:00) - – Data science’s role in marketing
(23:00) - – Balancing brand bets with ROI
(28:00) - – Inside the “Love Your Work” campaign
(35:00) - – How Canva executes large campaigns
(39:00) - – Building enterprise credibility and trust
(42:00) - – FedEx case study on brand governance
(46:00) - – Lessons from Google and Meta
(50:00) - – Why creativity is a marketing superpower
(52:00) - – Closing thoughts

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

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Brought to you by:

Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive.

Convertiv - A B2B marketing agency that helps enterprise teams build an AI-powered go-to-market strategy, specializing in AEO. Podcast listeners get a free AI search review showing how you stack up against competitors. Learn more at convertiv.com/exitfive.

Optimizely - the AI platform for marketers. Build your own AI agents or pull from a directory of 50+ pre-built ones for marketing use cases. Their new Virtual Teammates can join meetings, complete tasks, support campaigns, and keep your website optimized. Learn more at optimizely.com/exitfive.

Compound Growth Marketing- A full-funnel demand gen agency helping high-growth cybersecurity and enterprise software companies show up earlier in the buying journey, combining AEO, modern paid advertising, and a dedicated go-to-market engineering team. Podcast listeners get two free media planning sessions to find out what channels are driving the best ROI. Learn more at compoundgrowthmarketing.com/exitfive.

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.

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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

How to Lead Marketing Through the AI Shift with Bill Glenn (SVP of Marketing at Esper) Feb 10, 2026

Show notes

#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
(02:45) - What Esper does and why software powering hardware matters
(05:30) - Why AI feels like the early internet shift
(07:20) - Leading with curiosity instead of pretending to be an AI expert
(10:00) - Why AI adoption is a behavior change problem, not a tools problem
(12:00) - How Esper is rolling out AI with guardrails across the company
(17:45) - Why “boring AI” that saves time matters most
(19:00) - Phase 1 vs Phase 2 AI adoption in marketing teams
(29:10) - AI, mentorship, and preparing the next generation of marketers
(41:55) - Leadership advice for first-time CMOs and VPs
(47:00) - Final takeaways and wrap-up

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

***

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

How to Use AI for Content Without Creating Slop with Eoin Clancy (VP Growth at Airops) Feb 04, 2026

Show notes

#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
(02:23) - What Airops does and the AI search problem they’re solving
(03:18) - What a “content engineer” actually is
(14:58) - How to use AI without creating AI slop
(18:14) - The 3 signals content is AI slop
(31:24) - Why webinars are Airops’ best growth channel
(33:49) - How they choose webinar topics and guests
(50:01) - Other channels working (enablement, community, events)
(53:01) - Final takeaways and wrap-up

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

***

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

How To Drive Revenue Through Content with Lashay Lewis (Founder, Authority Plug) Jan 29, 2026

Show notes

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/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

***

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

How Marketing Leaders are Thinking About AEO Jan 27, 2026

Show notes

#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
(03:53) - Meet the panel: marketing leaders from Webflow, EagleView, and Piedmont Global
(07:31) - How AI search is changing buyer behavior vs traditional Google search
(11:14) - EagleView’s real approach to AI search, greenfield opportunities, and prompt tracking
(14:21) - What “black hat” vs “white hat” tactics look like in AI-driven search
(18:28) - Webflow’s take: integrated marketing, generosity, and building useful tools
(26:25) - Getting past high-level advice and into real execution
(31:25) - “Circle the buyer”: how content builds demand before buyers are in-market
(35:08) - Why PR is back: long-form press, citations, and brand credibility in AI search
(42:08) - 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/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

***

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

How to Master B2B Positioning with Anthony Pierri (Fletch PMM) Jan 22, 2026

Show notes

#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/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

***

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

How to Stand Out in B2B Marketing (with Louis Grenier, Author of Stand the F*ck Out) Jan 19, 2026

Show notes

#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
(03:40) - — The colonoscopy story.
(11:00) - — Trojan Horse marketing. Get attention first. Sell later. Stop leading with your product.
(16:00) - — Why you can’t create demand, only redirect it.
(21:40) - — Category creation vs sub-categories. Most startups get this wrong.
(24:30) - — Meaning-free brand assets. Why weird mascots and visuals actually work.
(30:10) - — How to sell bold ideas internally without asking for permission.
(34:00) - — Ads that look like ads fail. Attention is the job.
(42:40) - — Triggers vs pain points. How people actually decide to buy.
(48:00) - — 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/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

***

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

Influencer Marketing, Podcasting Strategy, and Brand Driving Demand with Jess Cook (VP Marketing at Vector) Jan 15, 2026

Show notes

#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?
(05:55) - — B2B Influencer pilot setup: why this channel, why now
(13:13) - — The result: 45 demos, ~$1.1M pipeline, and how she tracked it
(15:11) - — How to run influencers
(20:36) - — Scaling idea: retainer-style influencer partnerships
(22:52) - — Vector’s podcast: “awareness magnet” and the format that works
(25:16) - — The production system: in-person batch recording a full season in 2 days
(39:02) - — Jess’s LinkedIn strategy: why she started posting and what she optimizes for
(50:50) - — 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/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

***

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

How to Build a Community People Trust with Matt Carnevale Jan 12, 2026

Show notes

#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
(06:45) - – What “community” actually means (and what it definitely isn’t)
(11:30) - – Why most B2B communities fail before they ever get traction
(16:10) - – Community vs. content: what gets people in vs. what makes them stay
(20:45) - – Why Slack groups aren’t a strategy
(25:30) - – Treating community like a product, not a marketing channel
(31:40) - – The role of trust, curation, and saying no to the wrong people
(37:15) - – What community managers actually do behind the scenes
(44:10) - – How in-person events changed the Exit Five community
(50:20) - – 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/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

***

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

How B2B Marketers Are Actually Using AI at Work with Jess Lytle Jan 08, 2026

Show notes

#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
(04:30) - – Meet Jess Lytle, Head of Marketing at Exit Five
(06:44) - – How Jess got hired at Exit Five (webinar → DMs → job)
(08:44) - – From demand gen to AI: early adoption, teaching, and Lovable
(14:14) - – Why AI feels different than traditional martech
(16:44) - – Content in 2026: originality, human insight, and AI distribution
(26:08) - – NotebookLM: real marketing workflows and internal use cases
(32:08) - – AI tools, team structure, and hybrid marketer roles
(42:48) - – Working at Exit Five, founder-led marketing, and brand bets

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter

Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

***

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

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