#261 AI & Creativity | In this episode, Dave is joined by Mark Schaefer, marketing strategist, keynote speaker, and author of 11 books, including his latest, Audacious: How Humans Win in an AI Marketing World. Mark has spent decades studying the intersection of marketing, tech, and human behavior, and his ideas have helped reshape how B2B brands think about relevance, creativity, and differentiation in a noisy digital world.

Dave and Mark cover:

• Why playing it safe is the biggest threat to B2B marketers in the AI era
• How to create marketing that actually connects by disrupting the story, the channel, or the storyteller
• Real examples of B2B brands ditching “best practices” and standing out with emotional, human-first marketing

You’ll come away with a fresh perspective on how to stay relevant, creative, and impactful, especially as AI becomes a bigger part of your marketing stack.

Timestamps

• (00:00) - – Intro

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Zuddl.

We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.

Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.

Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.

On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.

If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. 

Head over to zuddl.com/exitfive to learn more. 

#260 Product Marketing | Dave is joined by Matt De Vincentis, VP of Product Marketing at Atlassian. With a background that spans engineering, product marketing, and leadership at companies like VMware and Palo Alto Networks, Matt shares how Atlassian structures its product marketing team, prioritizes work, and stays tied to business outcomes, even at massive scale.

Dave and Matt cover:

• How Atlassian connects product marketing to revenue and pipeline (and why PMMs need to “own the outcome”)
• How to build high-trust, high-impact marketing teams, drawing on lessons from firefighting and enterprise leadership
• The async work philosophy Atlassian uses to eliminate unnecessary meetings and increase productivity across a global team

Whether you lead a team or want a seat at the table, this episode breaks down how to structure, scale, and lead product marketing the Atlassian way.

Timestamps

• (00:00) - – Intro

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Zuddl.

We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.

Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.

Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.

On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.

If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. 

Head over to zuddl.com/exitfive to learn more. 

#259 Paid Ads | In this episode, Dave is joined by Pranav Piyush, founder and CEO of Paramark, a platform helping B2B marketers run real experiments to measure ad performance. Pranav brings a sharp point of view on attribution, channel performance, and how to actually prove what’s working across your paid media mix.

Dave and Pranav cover:

• Real-world results from 7 B2B ad campaigns, including branded search, YouTube, billboards, and Performance Max
• Why most marketers are misusing the word “test” and how to run true experiments with lift, control, and causality
• How even small teams can apply experiment design (on a $10K budget or less) to make smarter spend decisions

Whether you're managing a big budget or just getting started with paid campaigns, this episode will help you think more critically, and confidently, about where and how to invest in B2B marketing.

Timestamps

• (00:00) - – Intro

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Zuddl.

We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.

Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.

Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.

On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.

If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. 

Head over to zuddl.com/exitfive to learn more. 

Dave here. Interrupting the regular podcast feed for a 3 minute story and rant about why I love the job of marketing and what it might mean in a world where AI is advancing so rapidly and changing the role of marketing.

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Zuddl.

We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.

Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.

Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.

On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.

If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. 

Head over to zuddl.com/exitfive to learn more. 

#257 AI Strategy | Dave is joined by Kieran Flanagan, SVP of Marketing at HubSpot and former CMO at Zapier. Kieran is a rare blend of technical operator, creative strategist, and team builder. He’s spent his career pushing the edges of B2B marketing, most recently through his work leading AI transformation initiatives at scale.

Dave and Kieran cover:

• How AI is reshaping B2B marketing workflows, content creation, and team structure
• Why the best marketers will specialize at the “outer edges” of creativity or technical execution (and what happens if you stay stuck in the middle)
• Kieran’s leadership philosophy: how he manages 300+ people while staying deeply involved in creative execution

Whether you’re leading a marketing team or sharpening your own skills, this episode offers a clear look at how AI is changing the game and how B2B marketers can stay creative, strategic, and indispensable in the process.

Timestamps

• (00:00) - – Intro

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Zuddl.

We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.

Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.

Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.

On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.

If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. 

Head over to zuddl.com/exitfive to learn more. 

#256 Email Deliverability | In this episode, Dan is joined by Sarah McNamara, Revenue Operations & GTM Strategy Lead at Vector, and Alex Fine, co-founder of Understory, an agency helping B2B SaaS companies scale with outbound, paid, and email. Both Sarah and Alex are experts in email strategy, specifically the behind-the-scenes mechanics that make or break your deliverability.

They break down what B2B marketers often overlook when it comes to getting emails opened, read, and replied to, and share practical tactics to improve performance across newsletters, outbound, and lifecycle campaigns.

Dan, Sarah, and Alex cover:

• Why email deliverability issues are more common than you think and how to spot them early
• The metrics that actually matter (hint: opens and clicks aren’t on the list)
• How to protect your domain reputation and warm up inboxes the right way

If email is part of your GTM motion, this episode will help you reach more inboxes and stop your messages from disappearing into the void.

Timestamps

• (00:00) - – Intro

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Zuddl.

We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.

Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.

Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.

On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.

If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. 

Head over to zuddl.com/exitfive to learn more. 

#255 Leadership | In this episode, Dave is joined by Kelly Hopping, CMO of Demandbase, a B2B company known for pioneering account-based marketing. Kelly leads a 70+ person marketing org that spans brand, demand gen, product marketing, events, and SDRs, and she shares exactly how she structures and operates that team to drive results.

Dave and Kelly cover:

• How to design and run a full-funnel marketing team that includes SDRs, content, field, and brand, and keep them aligned on pipeline
• The annual planning strategy Kelly uses to balance short-term targets with long-term positioning (including what changes quarter to quarter)
• How her team is using AI right now and what she’s doing personally to stay sharp as the pace of change accelerates

Whether you're a first-time CMO or just trying to scale your B2B marketing engine, this one is packed with insights from someone who’s operating at a high level.

Timestamps

• (00:00) - – Intro

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Zuddl.

We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.

Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.

Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.

On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.

If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. 

Head over to zuddl.com/exitfive to learn more. 

#254 Brand | In this episode, Dave sits down with Kira Federer, VP of SMB Marketing at Paramount Advertising, and formerly at companies like Reddit and Glassdoor. Kira shares her journey from sales to product marketing and the lessons she’s learned along the way.

Dave and Kira discuss:

• How to align marketing and sales through co-creation to ensure your sales team uses the content you create
• The value of a strong messaging framework and how it drives consistency in B2B marketing
• Why you need to time your product launches and ensure that marketing resonates with both your team and the market at the right moment

Timestamps

• (00:00) - - Intro to Kira

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Zuddl.

We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.

Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.

Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.

On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.

If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. 

Head over to zuddl.com/exitfive to learn more. 

#253 Lifecycle Marketing | In this episode, we’re joined by two expert lifecycle marketers: Charlotte Hardin, Lifecycle Marketing Manager at Rebuy Engine, and Naomi West, Senior Product Manager at Customer.io. Charlotte and Naomi bring years of hands-on experience running email, onboarding, and retention programs inside B2B SaaS companies.

They break down how B2B teams can use lifecycle marketing to drive more revenue, boost product engagement, and strengthen customer relationships, without needing a massive team.

Charlotte and Naomi cover:

• How top B2B teams build high-performing welcome sequences, and why they’re constantly worth revisiting
• The role of experimentation and how to prioritize AB tests that deliver learnings (even with small audiences)
• Strategic ways to keep users engaged post-onboarding, including behavior-based triggers and surprise-and-delight moments

Timestamps

• (00:00) - – Intro

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Zuddl.

We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.

Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.

Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.

On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.

If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. 

Head over to zuddl.com/exitfive to learn more. 

#252 Category Creation | Dave is joined by Josh Lowman, Founder and Creative Director of Gold Front, a category design studio that’s worked with brands like Uber, Notion, and Qualtrics. Josh is a leading voice in strategic brand positioning and category creation. He’s spent over a decade helping high-growth B2B companies define what makes them irreplaceable in crowded markets.

Dave and Josh cover:

• Why most category creation efforts fail (and what to do instead)
• The four real paths to category leadership: create, transform, niche, or go solo
• How B2B marketers can align product, brand, and messaging around a single strategy to stand out and scale

Whether you're launching a new product or repositioning an existing one, this episode is a masterclass in strategic clarity.

Timestamps

• (00:00) - – Intro

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

Today’s episode is brought to you by Zuddl.

We’re halfway through 2025, and one thing’s clear: events continue to be one of the highest performing marketing channels. Niche meetups, conferences, curated dinners, networking - you name it. Everyone’s leaning in.

Events are a core part of our playbook this year at Exit Five. So far, we’ve hosted two virtual sessions each month, one large virtual event, one in-person meetup, and we’re deep in the weeds planning our Drive conference coming back to Vermont this September.

Zuddl helps us run a smarter event strategy - from driving registrations, managing invites, automating comms, reminders, analytics, tracking. Their Salesforce integration also makes it simple to report on pipeline and revenue from events without pulling in ops.

On top of that, the differentiator with Zuddl is how their team is insanely good at supporting us. They always go above and beyond for us - and that’s how we’ve been able to keep the momentum going with 12+ events already this year, with plenty more to come.

If events are part of your marketing strategy, you need to look at Zuddl to see how companies like Zillow, CrowdStrike, and Iterable are using the top event platform for Business events in 2025. 

Head over to zuddl.com/exitfive to learn more.