#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

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:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive.

AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.

Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. 

***

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

#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

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:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive.

AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.

Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. 

***

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

#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:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive.

AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.

Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. 

***

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

#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 [email protected] - 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:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive.

AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.

Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. 

***

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

#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

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:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive.

AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.

Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. 

***

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

#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

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:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive.

AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.

Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. 

***

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

#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

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:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive.

AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.

Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. 

***

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

#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 brand recall.

Matt and Amrita cover:

• Why offline ads like billboards and transit campaigns are making a comeback in B2B marketing
• How creative choices — bold colors, emotional messaging, and relatable personas — can make or break brand campaigns
• What B2B marketers should know about budget allocation, measuring recall, and balancing brand vs. performance marketing

Whether you’re running your first brand campaign or rethinking your spend mix, this episode will give you fresh ideas on how to stand out in B2B marketing.

Timestamps

• (00:00) - – Intro

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:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive.

AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.

Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. 

***

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

#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 even when you're not the Subject Matter Expert
• Signal-based marketing and how it is transforming the buyer’s journey by focusing on the right actions instead of just clicks
• B2B influencer marketing plays that work

Timestamps

• (00:00) - - Intro to Kevin

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:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive.

AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.

Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. 

***

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

#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.

Dave and Pranav cover:

• How to translate your company narrative into concrete marketing campaigns and creative hooks across channels
• Why creative output (not measurement) is the biggest bottleneck for most B2B marketing teams today
• The frameworks like category entry points, jobs-to-be-done, and behavioral psychology that help marketers spark fresh, testable campaign ideas month after month

You can expect a practical, example-filled conversation on turning strategy into execution and building a creative engine that never runs dry.

Timestamps

• (00:00) - – Intro and audience roll call

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:

Optimizely - A no-code AI platform where autonomous agents execute marketing work across webpages, email, SEO, and campaigns. Get a free, personalized 45-minute AI workshop to help you identify the best AI use cases for your marketing team and map out where agents can save you time at optimizely.com/exitfive.

AirOps - The content engineering platform that helps marketers create and maintain high-quality, on-brand content that wins AI search. Go to airops.com/exitfive to start creating content that reflects your expertise, stays true to your brand, and is engineered for performance across human and AI discovery.

Visit exitfive.com/retreat to apply for Exit Five’s first-ever, in-person Marketing Leadership Retreat, March 18–20, 2026 in Scottsdale, Arizona. Join 100 CMOs and VPs of Marketing from companies like like Zoom, Snowflake, Manychat, Bitly, G2, HP, and more for two days of thinking bigger around a trusted group of peers in marketing. 

***

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