The Exit Five Podcast

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I Answered 15 Questions About Work and Life from the Exit Five Team Oct 27, 2025

Show notes

#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 I’m reading, and a few personal stories I’ve never shared before.

Watch this episode on YouTube on my channel: https://www.youtube.com/watch?v=EyagkJf6xHw&t=508s

Timestamps

(00:00) - – Intro
(01:00) - – What’s your LinkedIn content creation process?
(03:45) - – How often do you check Slack and email?
(04:45) - – What are you reading or listening to right now?
(08:15) - – What does a perfect day look like for you?
(10:15) - – Tell your life story in four minutes.
(11:00) - – If you could gain any quality or ability, what would it be?
(15:00) - – What’s your most embarrassing work moment?
(16:00) - – What’s your favorite all-time book and why?
(17:00) - – What’s the best career advice you’ve ever received?
(19:20) - – What motivates you when you’re feeling unmotivated?
(20:25) - – If you could transform into any animal, what would you choose?
(21:00) - – What are your biggest pet peeves?
(22:50) - – Which team member would you swap lives with for a day?
(24:00) - – What’s your go-to karaoke song?
(24:35) - – If you weren’t running Exit Five, what job would you have?
(26:15) - – Wrap-up & closing

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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.

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From Growth Marketer to CMO: How Kelly Cheng Leads Marketing at Goldcast Oct 23, 2025

Show notes

#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
(02:00) - – Kelly’s path from Hong Kong to Boston
(05:00) - – Joining Goldcast and the PLG pivot
(08:00) - – Moving from growth marketer to CMO
(11:00) - – The role of mentors in her career
(19:00) - – Questions to ask before taking a CMO role
(25:00) - – Inside Goldcast’s marketing org structure
(31:00) - – How Kelly measures brand and mindshare
(38:00) - – Why the BDR team reports to marketing
(44:00) - – The link between brand, content, and pipeline
(49:00) - – Leading with vulnerability and the “long game”

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

Live from LGA my NYC Recap Oct 20, 2025

Show notes

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 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

Mastering Messaging, Copy, and Clarity with Emma Stratton Oct 20, 2025

Show notes

#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 using specificity and buyer empathy
Why most B2B messaging blends into the “sea of sameness” (and how to stand out)
How customer research and real conversations create message–market fit

They wrap with a candid chat on journaling, focus, and how managing your mental energy can make you a better marketer and human.

Timestamps

(00:00) - – Intro to Emma
(03:05) - – What makes B2B messaging actually good
(06:47) - – Common messaging mistakes (and why “clarity > clever”)
(09:45) - – Positioning vs. messaging: what’s the difference?
(13:58) - – Why it’s hard to name great B2B marketing examples
(16:22) - – How to sharpen weak messaging and fix vague positioning statements
(19:30) - – Simplifying complex products without dumbing it down
(22:40) - – How to write for buyers (not just execs)
(26:12) - – Using customer interviews and research to build strong messaging
(30:50) - – Standing out in a crowded, buzzword-filled market
(33:34) - – How storytelling fits into B2B messaging
(36:40) - – Messaging advice for early-stage founders and startups
(39:55) - – How often should you revisit and update messaging?
(42:05) - – Productivity, managing your energy, and staying focused
(45:20) - – Journaling, mindfulness, and being intentional with your time
(49:15) - – Final takeaways

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

Behind the Scenes of Drive 2025 with Anna Vermillion and Allison Saxon Oct 16, 2025

Show notes

#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
(01:00) - – Why events are making a comeback in B2B marketing
(05:00) - – What Drive is and how it started
(10:00) - – Why every event should start with the landing page
(13:00) - – Lessons from year one and how feedback shaped Drive 2025
(18:00) - – Treating events like products, not projects
(20:00) - – Building connection through “third spaces” and excursions
(25:00) - – Why community is the real ROI of in-person events
(30:00) - – The biggest Drive mishap (and what it taught us)
(35:00) - – Post-event strategy: why the event isn’t over when it ends
(45:00) - – Favorite moments, lessons, and shoutouts from Drive 2025

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

Email vs. Real Mail Oct 15, 2025

Show notes

#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 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

Traveling and The ROI of Events Oct 14, 2025

Show notes

#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 work, and other ramblings.

*If you listened to this: DM me on LinkedIn or email dave@exitifve.com - tell me what you want me to cover on this podcast as it relates to marketing, business, or life.

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

Beyond Copy: How To Use AI to Build GTM Systems That Scale Oct 13, 2025

Show notes

#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, Zapier, and AirOps to build repeatable GTM systems that scale without burning bandwidth
The frameworks behind automating webinar production, sales transcript analysis, and content refreshes with AI
Why marketers need to bridge the gap between AI hype and real execution, and where to start with building practical workflows

Together, they break down the exact tools, prompts, and processes they’re using to turn AI from theory into impact across B2B marketing teams.

Timestamps

(00:00) - – Intro
(01:00) - – The gap between AI hype and real execution
(05:00) - – Dan’s background and how GTM Engineering came to life
(08:00) - – Building repeatable webinar systems with Clay
(12:00) - – How to scale content and events without burning bandwidth
(17:00) - – Eoin’s content creation workflow using AirOps
(22:00) - – Turning sales transcripts into actionable GTM insights
(31:00) - – Using Zapier Agents to automate product marketing tasks
(39:00) - – Refreshing SEO content with AI for better performance
(47:00) - – Where AI fits in your team and how to start small

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

Events, AI, and The Future of B2B Buying with Sydney Sloan, CMO at G2 Oct 09, 2025

Show notes

#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 marketplaces in the world.

Dave and Sydney cover:

How to design events that truly drive pipeline, using frameworks like “Think, Feel, Do” to plan with purpose
A smarter way to measure event ROI with Sydney’s “Revenue in the Room” approach
How AI is transforming the buyer journey and reshaping what modern marketing teams look like

An episode that will leave you rethinking your marketing strategy, from the events you run to the org you build.

Timestamps

(00:00) - – Intro
(02:00) - – The return of in-person events
(05:00) - – Building community through smarter event design
(07:00) - – Inside G2’s “AI in Action” roadshow
(10:00) - – The “Think, Feel, Do” event framework
(13:00) - – Why details make or break events
(16:00) - – Measuring success with “Revenue in the Room”
(19:00) - – Post-event follow-up that drives results
(25:00) - – How AI is reshaping the buyer journey
(41:00) - – Rethinking marketing orgs for the AI era

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

Marketing in the Age of AI: CMOs Separating the Hype from What’s Real Oct 06, 2025

Show notes

#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 leaders are adapting.

Dave and the panel cover:

The most overhyped AI use cases in B2B marketing (and where human nuance still wins)
Real success stories, including building an AI-powered content research engine, scaling global localization, and using AI to make creative teams more data-driven
How CMOs are personally using AI as a strategic thought partner for board prep, customer insights, and team coaching

Whether you’re experimenting with new tools or figuring out how to bring AI into your strategy, this conversation gives a grounded look at what B2B marketing leaders are really doing today.

Timestamps

(00:00) - – Intro
(02:00) - – Meet the panel: SOCi, Knak, Bitly
(06:00) - – Has AI met or missed expectations?
(10:45) - – The most overhyped AI use cases
(14:00) - – Why human nuance still matters in personalization
(19:00) - – The imposter syndrome of AI adoption
(22:00) - – The power of AI with memory
(24:40) - – Best AI use cases from the panel
(29:00) - – Scaling global localization with AI
(32:00) - – Training brand teams to be more data-driven
(36:00) - – How CMOs personally use AI in their workflow
(40:00) - – Using AI as a strategic thought partner
(44:00) - – Coaching teams with AI feedback loops
(46:00) - – The frustrations of iteration and tool updates
(50:00) - – Is leadership pushing AI adoption?
(54:00) - – Budgeting and building a modern AI-enabled tech stack
(57:00) - – Final takeaways and closing

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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