#267 Product Marketing | Matt is joined by Jennifer Cannizzaro, VP of Product Marketing at Responsive and former marketing leader at Whoop and DocuSign. Jennifer brings deep experience in building strategic, insight-driven marketing teams at high-growth B2B companies and she’s at the forefront of using AI to scale smarter, not just faster.

Matt and Jennifer cover:

• How product marketing can become a company-wide growth lever through tighter GTM alignment, strategic planning, and better customer intel
• Practical ways her team is using AI to reduce content workload, cut freelancer spend, and increase speed-to-market
• How to coach marketers to use AI responsibly, and why curiosity and judgment matter more than ever

It’s a tactical, behind-the-scenes look at what high-impact product marketing really looks like in 2025, including strategy, systems, and AI.

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. 

#266 Marketing Leadership | In this episode, Matt is joined by Jess Cook, Head of Marketing at Vector, a platform pioneering the contact-based marketing category. Jess has spent her career building standout content strategies at B2B brands like LASSO and Fastly, and she recently made the jump from Head of Content to first-time Head of Marketing.

Jess and Matt cover:

• How content marketers can transition into marketing leadership and what gaps to prepare for
• The strategy behind building a brand that stands out in B2B (and why Vector leans into being “a little unhinged”)
• How Jess built her first marketing budget from scratch and sold it in using storytelling, not spreadsheets

You’ll walk away with tactical insights on running a modern B2B marketing org, from content and brand to budgeting and team structure.

Timestamps

• (01:00) - – Jess’s B2C roots at McDonald’s and Kellogg

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. 

#265 Non-SaaS Marketing | In this episode, Matt sits down with Sandra Rand, a fractional head of marketing who works with early-stage, non-SaaS B2B companies. She’s led marketing for PE-backed, self-funded, and services-based businesses, where big budgets and SaaS-style playbooks aren’t the norm. She’s also building the Non-SaaS Marketers subgroup inside Exit Five to support others facing the same challenges.

Matt and Sandra cover:

• How non-SaaS teams drive growth without demos, PLG, or huge lead volume
• Why events, word of mouth, and referrals often outperform funnels in these orgs
• Tactical ideas for gifting, partnerships, and pipeline-building on a lean budget

Whether you work in SaaS or not, you’ll walk away with creative, scrappy strategies to build trust and drive results in B2B.

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. 

#264 Async Work | In this episode, Dave is joined by Ashley Faus, Director of Lifecycle Marketing at Atlassian, and Dr. Molly Sands, Head of the Teamwork Lab at Atlassian. Ashley brings deep experience in cross-functional B2B marketing leadership, while Molly leads a team of behavioral scientists designing better ways for teams to collaborate. Together, they unpack how Atlassian has rethought marketing org structure, internal comms, and meetings to drive higher output with fewer syncs.

Dave, Ashley, and Molly cover:

• The framework Atlassian uses to reduce meetings and communicate asynchronously (including how to structure updates that actually get read)
• How to balance transparency with clarity and avoid information overload across Slack, Loom, and Confluence
• Tactical ways to structure team rituals, recurring meetings, and brainstorms to focus on output, not performative busywork

You’ll walk away knowing how to run a leaner, more effective marketing team (without drowning in Slack and Zoom).

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. 

#263 Marketing Strategy | Dave is joined by Jason Lyman, CMO at Customer.io, a customer engagement platform used by over 7,500 companies. Jason has led marketing at Dropbox, BetterCloud, and now heads a 30-person team driving growth across both PLG and sales-led motions.

Dave and Jason cover:

• How to structure a B2B marketing org for scale, alignment, and channel ownership
• Why events are their #1 channel and how creative formats drive real pipeline
• The KPI + OKR system they use to prioritize work and measure marketing’s impact

You’ll walk away with a clearer understanding of how to design your team, focus your strategy, and invest in channels that actually drive results.

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. 

#262 Content Strategy | Dave sits down with Chelsea Castle, Head of Content and Brand at Close. Chelsea talks about her experience in B2B SaaS and shares how to build impactful content that resonates with your audience.

Chelsea and Dave cover:

• How leveraging internal and cross-functional knowledge can create a content goldmine
• Why it is important to repurpose podcast episodes, webinars, and other media into multiple forms of content to maximize their value
• Strategies for integrating SEO with authentic, valuable content that resonates with your audience, beyond just ranking for keywords

Timestamps

• (00:00) - - Intro to Chelsea

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. 

#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.