#300 Drive | This episode is from Drive 2025, our 2-day in-person event for B2B marketers in Burlington, VT. It features Diane Wiredu, Founder of Lion Words and expert in B2B messaging and positioning. She shared a killer talk on “What Your Messaging Is Missing,” breaking down why most B2B copy sounds the same and how to close the meaning gap by focusing on clarity, balance, and buyer context.

Head over to exitfive.com/drive to join the waitlist for Drive 2026 and be the first to know when tickets go on sale.

Timestamps

• (00:00) - – Intro from Dave
• (02:52) - – What “message-market fit” actually means
• (05:22) - – Why most B2B messaging misses
• (09:27) - – The “meaning gap” and why it happens
• (14:12) - – Balancing clarity, emotion, and differentiation
• (19:37) - – How to simplify complex products
• (26:33) - – Examples of messaging that actually resonates
• (32:03) - – How to pressure-test your messaging
• (38:18) - – Aligning teams around a clear message
• (44:03) - – Turning insights into copy that converts
• (49:13) - – Q&A: internal buy-in, testing, next steps

Join 50,000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Today’s episode is brought to you by Paramark.

It’s November. 2026 planning is already here. And the stuff you’re doing right now will decide how next year plays out.

But here’s the problem: most teams are still planning next year's marketing strategy based on the WRONG DATA because of broken attribution and a misleading gut feel. And you can’t make smart budget calls if you’re just guessing what’s working, what’s not, and where to put your next dollar.

That’s where Paramark comes in. They help you replace the guesswork with actual insight backed by $2 billion in analyzed marketing data. They’ve figured out what actually drives incremental growth across every channel including LinkedIn, Meta, TikTok, Google, CTV, even OOH.

And right now, they’re offering a private 1:1 consultation with their CEO and CMO, Pranav and Sam, who have led marketing teams at companies like Dropbox, Adobe, Microsoft, and Shutterfly.

In this 45-minute strategy session, they’ll help you measure the real impact of every marketing dollar, pull insights from your current media mix, and design a 2026 roadmap that’s rooted in data, not gut.

This is a heck of an offer. And it’s real. And will go fast. So if you want to future-proof your marketing strategy for 2026, don’t miss out on this offer.

Grab your spot at paramark.com/brand-consult.

***

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

#299 Drive | This episode is from Drive 2025, our 2 day in-person event for B2B marketers in Burlington, VT. Our first speaker was Sangram Vajre, Co-founder and CEO of GTM Partners and expert in GTM strategy. He shared a great session on building a repeatable GTM Operating System for sustainable growth, offering insight from 100 companies on what separates teams that scale from those that stall.

Head over to exitfive.com/drive to join the waitlist for Drive 2026 and be the first to know when tickets go on sale.

Timestamps

• (00:00) - – Intro from Dave
• (02:08) - – Sangram’s background + setup
• (04:08) - – What GTM really means
• (11:03) - – The 3 stages of GTM maturity
• (11:28) - – Why NRR is the key metric
• (20:08) - – The “boring marketing” advantage
• (26:43) - – How to say no and prioritize
• (28:43) - – Why GTM alignment beats tactics
• (32:43) - – Building your GTM Operating System
• (35:03) - – Q&A: GTM alignment, discovery, growth

Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Today's episode is brought to you by Knak.

Email (in my humble opinion) is the still the greatest marketing channel of all-time.

It’s the only way you can truly “own” your audience.

But when it comes to building the emails - if you’ve ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever.

That’s why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.

• Frustrated by clunky email builders? You need Knak.
• Tired of ‘hoping’ the email you sent looks good across all devices? Just test in Knak first.
• Big team making it hard to collaborate and get approvals? Definitely Knak.

And the best part? Everything takes a fraction of the time.

See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.

***

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

#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
• (02:08) - – What’s your LinkedIn content creation process?
• (04:53) - – How often do you check Slack and email?
• (05:53) - – What are you reading or listening to right now?
• (09:23) - – What does a perfect day look like for you?
• (11:23) - – Tell your life story in four minutes.
• (12:08) - – If you could gain any quality or ability, what would it be?
• (16:08) - – What’s your most embarrassing work moment?
• (18:43) - – What’s your favorite all-time book and why?
• (19:43) - – What’s the best career advice you’ve ever received?
• (22:03) - – What motivates you when you’re feeling unmotivated?
• (23:08) - – If you could transform into any animal, what would you choose?
• (23:43) - – What are your biggest pet peeves?
• (25:33) - – Which team member would you swap lives with for a day?
• (26:43) - – What’s your go-to karaoke song?
• (27:18) - – If you weren’t running Exit Five, what job would you have?
• (28:58) - – Wrap-up & closing

Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Today's episode is brought to you by Knak.

Email (in my humble opinion) is the still the greatest marketing channel of all-time.

It’s the only way you can truly “own” your audience.

But when it comes to building the emails - if you’ve ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever.

That’s why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.

• Frustrated by clunky email builders? You need Knak.
• Tired of ‘hoping’ the email you sent looks good across all devices? Just test in Knak first.
• Big team making it hard to collaborate and get approvals? Definitely Knak.

And the best part? Everything takes a fraction of the time.

See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.

***

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

#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
• (03:08) - – Kelly’s path from Hong Kong to Boston
• (06:08) - – Joining Goldcast and the PLG pivot
• (09:08) - – Moving from growth marketer to CMO
• (12:08) - – The role of mentors in her career
• (20:08) - – Questions to ask before taking a CMO role
• (27:43) - – Inside Goldcast’s marketing org structure
• (33:43) - – How Kelly measures brand and mindshare
• (40:43) - – Why the BDR team reports to marketing
• (46:43) - – The link between brand, content, and pipeline
• (51:43) - – Leading with vulnerability and the “long game”

Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Today's episode is brought to you by Knak.

Email (in my humble opinion) is the still the greatest marketing channel of all-time.

It’s the only way you can truly “own” your audience.

But when it comes to building the emails - if you’ve ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever.

That’s why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.

• Frustrated by clunky email builders? You need Knak.
• Tired of ‘hoping’ the email you sent looks good across all devices? Just test in Knak first.
• Big team making it hard to collaborate and get approvals? Definitely Knak.

And the best part? Everything takes a fraction of the time.

See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.

***

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

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

***

Today's episode is brought to you by Knak.

Email (in my humble opinion) is the still the greatest marketing channel of all-time.

It’s the only way you can truly “own” your audience.

But when it comes to building the emails - if you’ve ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever.

That’s why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.

• Frustrated by clunky email builders? You need Knak.
• Tired of ‘hoping’ the email you sent looks good across all devices? Just test in Knak first.
• Big team making it hard to collaborate and get approvals? Definitely Knak.

And the best part? Everything takes a fraction of the time.

See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.

***

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

#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
• (04:13) - – What makes B2B messaging actually good
• (07:55) - – Common messaging mistakes (and why “clarity > clever”)
• (10:53) - – Positioning vs. messaging: what’s the difference?
• (15:06) - – Why it’s hard to name great B2B marketing examples
• (17:30) - – How to sharpen weak messaging and fix vague positioning statements
• (20:38) - – Simplifying complex products without dumbing it down
• (23:48) - – How to write for buyers (not just execs)
• (28:55) - – Using customer interviews and research to build strong messaging
• (33:33) - – Standing out in a crowded, buzzword-filled market
• (36:17) - – How storytelling fits into B2B messaging
• (39:23) - – Messaging advice for early-stage founders and startups
• (42:38) - – How often should you revisit and update messaging?
• (44:48) - – Productivity, managing your energy, and staying focused
• (48:03) - – Journaling, mindfulness, and being intentional with your time
• (51:58) - – Final takeaways

Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Today's episode is brought to you by Knak.

Email (in my humble opinion) is the still the greatest marketing channel of all-time.

It’s the only way you can truly “own” your audience.

But when it comes to building the emails - if you’ve ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever.

That’s why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.

• Frustrated by clunky email builders? You need Knak.
• Tired of ‘hoping’ the email you sent looks good across all devices? Just test in Knak first.
• Big team making it hard to collaborate and get approvals? Definitely Knak.

And the best part? Everything takes a fraction of the time.

See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.

***

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
• (02:08) - – Why events are making a comeback in B2B marketing
• (06:08) - – What Drive is and how it started
• (11:08) - – Why every event should start with the landing page
• (14:08) - – Lessons from year one and how feedback shaped Drive 2025
• (19:08) - – Treating events like products, not projects
• (21:08) - – Building connection through “third spaces” and excursions
• (26:08) - – Why community is the real ROI of in-person events
• (32:43) - – The biggest Drive mishap (and what it taught us)
• (37:43) - – Post-event strategy: why the event isn’t over when it ends
• (47:43) - – Favorite moments, lessons, and shoutouts from Drive 2025

Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Today's episode is brought to you by Knak.

Email (in my humble opinion) is the still the greatest marketing channel of all-time.

It’s the only way you can truly “own” your audience.

But when it comes to building the emails - if you’ve ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever.

That’s why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.

• Frustrated by clunky email builders? You need Knak.
• Tired of ‘hoping’ the email you sent looks good across all devices? Just test in Knak first.
• Big team making it hard to collaborate and get approvals? Definitely Knak.

And the best part? Everything takes a fraction of the time.

See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.

***

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

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

***

Today's episode is brought to you by Knak.

Email (in my humble opinion) is the still the greatest marketing channel of all-time.

It’s the only way you can truly “own” your audience.

But when it comes to building the emails - if you’ve ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever.

That’s why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.

• Frustrated by clunky email builders? You need Knak.
• Tired of ‘hoping’ the email you sent looks good across all devices? Just test in Knak first.
• Big team making it hard to collaborate and get approvals? Definitely Knak.

And the best part? Everything takes a fraction of the time.

See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.

***

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