The Exit Five Podcast

Latest Episodes:

How Product Marketing Is Evolving in 2025: Lessons on AI and Leadership with Jennifer Cannizzaro Jul 24, 2025

Show notes

#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
(01:03) - – What product marketing owns today
(04:50) - – Launch and learn vs launch and leave
(06:00) - – How PMM drives company strategy
(09:25) - – Aligning teams around growth levers
(13:00) - – Gathering customer and market intel
(17:05) - – Quick, AI-powered research tactics
(18:45) - – Sharing insights across the org
(21:10) - – Real examples of AI in use
(24:30) - – Eliminating freelancer spend with AI
(26:10) - – What to feed AI to get results
(29:00) - – Coaching teams to use AI well
(32:30) - – Weekly AI spotlights and team habits
(34:45) - – Building a team-wide AI culture
(38:15) - – Setting realistic AI expectations
(42:00) - – Example prompts and experiments
(44:17) - – The role of community and mentorship
(50:30) - – Final thoughts and wrap-up

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***

Brought to you by:

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Convertiv - A B2B marketing agency that helps enterprise teams build an AI-powered go-to-market strategy, specializing in AEO. Podcast listeners get a free AI search review showing how you stack up against competitors. Learn more at convertiv.com/exitfive.

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Compound Growth Marketing- A full-funnel demand gen agency helping high-growth cybersecurity and enterprise software companies show up earlier in the buying journey, combining AEO, modern paid advertising, and a dedicated go-to-market engineering team. Podcast listeners get two free media planning sessions to find out what channels are driving the best ROI. Learn more at compoundgrowthmarketing.com/exitfive.

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.

***

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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How to Lead B2B Marketing for the First Time: Strategy, Budget, Team, and Content with Jess Cook Jul 21, 2025

Show notes

#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
(03:00) - – Jumping into B2B and growing through content
(04:45) - – Why she moved from Head of Content to Head of Marketing
(07:20) - – Hiring product marketing first (and why it matters)
(11:30) - – How Vector built a bold B2B brand with personality
(15:30) - – What Jess looked for in her first marketing hire
(18:50) - – Building and pitching her first full marketing budget
(24:15) - – Creating a 30/60/90 plan that actually drives buy-in
(25:45) - – Category content, SEO, and early wins with AI
(28:30) - – The podcast pivot: ditching “Funnel Cake” for something better
(32:10) - – How she knew Vector was the right fit
(35:50) - – Going all-in on YouTube and video-first strategy
(40:00) - – Short-form content, brand building, and trust
(42:30) - – Biggest lesson: balance long-term planning with quick wins
(47:00) - – Leading with action and setting the tone as a new marketing leader
(49:00) - – How Jess communicates vision and builds internal alignment
(52:30) - – Wrap-up and 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

Beyond the SaaS Playbook: How Non-SaaS Teams Drive Pipeline with Sandra Rand Jul 17, 2025

Show notes

#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
(01:30) - – Why Exit Five launched the Non-SaaS group
(06:50) - – What makes non-SaaS marketing different
(10:10) - – Budgets, sales cycles, and team structure
(15:00) - – Why brand and trust matter more
(17:10) - – Events > funnels in non-SaaS
(24:50) - – How to build brand on a budget
(30:20) - – Word-of-mouth and referral tactics
(35:00) - – Gifting and relationship-driven growth
(41:00) - – Scrappy, creative plays that actually work
(46:30) - – What’s next for the Non-SaaS community

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

The Atlassian Playbook for Building a Fast-Moving, Outcome-Driven Marketing Team Jul 14, 2025

Show notes

#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
(02:00) - – Why marketers showed up live: too many meetings, too little output
(05:00) - – Meet the guests: Ashley Faus and Dr. Molly Sands from Atlassian
(07:30) - – What “Team Anywhere” means at Atlassian
(09:30) - – The difference between information sharing and real connection
(12:00) - – Why marketing updates often fall flat internally
(14:00) - – How to communicate clearly inside the org (and get your message read)
(17:30) - – Structuring updates: topic, who it’s for, action, context
(20:30) - – When you need a meeting vs. when async works better
(24:30) - – “Sparring” meetings: real-time collaboration between equals
(27:00) - – What actually builds team connection (hint: not team happy hours)
(29:00) - – Async tools Atlassian uses across marketing
(31:30) - – Getting quiet team members to contribute in meetings
(34:00) - – How Atlassian runs recurring team rituals without wasting time
(38:00) - – Cross-functional alignment: structure, scorecards, and shared goals
(41:00) - – Best practices for async tools like Loom and Confluence
(44:00) - – Do brainstorming meetings even work? Here’s when they do.
(47:00) - – What to share with non-marketers (and what to skip)
(50:00) - – Why creating focus is the most underrated leadership skill
(52:00) - – Final takeaways from Ashley and Molly

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

Inside Customer.io’s B2B Marketing Strategy: Org, GTM, and Growth Channels with Jason Lyman Jul 10, 2025

Show notes

#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
(01:00) - – What Customer.io does and who they serve
(02:00) - – Growth story: from bootstrapped to private equity-backed
(04:00) - – Team size and breakdown of the 30-person marketing org
(06:00) - – Balancing PLG and sales-led within one team
(08:00) - – How the org is structured: focus teams vs. centers of excellence
(10:00) - – Aligning team goals to sales motions and funnel stages
(12:00) - – How Customer.io prioritizes internal marketing requests
(14:00) - – Avoiding the “who bangs the table loudest” trap
(15:00) - – Cross-functional alignment with sales and product
(17:00) - – KPI vs. OKR: how Customer.io uses both
(19:00) - – Examples of key KPIs for the business
(21:00) - – How OKRs cascade across the org
(23:00) - – Why structured goal setting leads to better marketing impact
(25:00) - – What channels are working: events are back
(26:00) - – Examples of creative event formats that build community
(28:00) - – Building pipeline without pitching at events
(30:00) - – How Customer.io defines and tracks long-term influence
(33:00) - – The decline of SEO and rise of AI-influenced buying
(35:00) - – Why positioning is more important than ever
(37:00) - – Product and marketing alignment in a modern org
(39:00) - – Selling both the product and the roadmap
(40:00) - – Jason’s one wish for marketers: better customer data
(42:00) - – Personalization, adaptability, and breaking through the noise
(43:00) - – Closing thoughts

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

Building a Brand Strategy and Content Goldmine with Chelsea Castle, Head of Content and Brand at Close Jul 07, 2025

Show notes

#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
(00:00) - - Merging Brand and Keyword-Driven Content
(00:01) - - Aligning Brand and Content Strategy with Your Goals
(00:08) - - New Content Channels for B2B
(00:12) - - How to Measure Content Engagement
(00:34) - - LinkedIn for B2B
(00:38) - - Chelsea’s Experience at Chili Piper
(00:43) - - Improving Content for Podcasts
(00:48) - - Driving Website Traffic Through Brand Content Strategy
(00:48) - - Skyscraper SEO Content Strategy
(00:56) - - How to Craft a Brand Strategy
(00:57) - - How to Grow Using Gated Content
(00:59) - - How to Maximize Search Impact

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

How to Stay Relevant as a Marketer in the World of AI with Mark Schaefer Jul 03, 2025

Show notes

#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
(02:00) - – Why most marketing is boring
(06:30) - – The danger of “best practices”
(10:30) - – Why AI is amplifying bad marketing
(14:00) - – The rise of raw, lo-fi, human content
(17:00) - – What AI can’t replicate: shared experiences
(20:30) - – Fear, risk, and the big brand trap
(24:00) - – Using AI to enhance, not replace, creativity
(28:00) - – The real framework behind Audacious
(31:00) - – B2B examples that break the mold
(36:30) - – Why now is the time to stand out
(41:00) - – Making bold marketing happen inside your org
(45:30) - – Liquid Death, Nutter Butter, and brand disruption
(50:00) - – B2B doesn’t mean boring
(54:00) - – The one question every marketer should ask

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

Inside Atlassian’s Product Marketing Strategy: Team Structure, Metrics, and Execution with Matt De Vincentis Jun 30, 2025

Show notes

#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
(01:30) - – Matt’s path from engineer to Atlassian VP
(04:45) - – Why technical backgrounds can be both a strength and a curse in PMM
(08:30) - – What product marketing looks like at a $5B company
(09:30) - – “Own the outcome, not the task”: tying PMM to revenue
(11:50) - – Why product marketers should care about pipeline (even if they don’t own it)
(13:15) - – How brand and creative marketers can still align to business outcomes
(15:45) - – Measuring inputs vs. outcomes (and how to stay focused on the right one)
(16:30) - – How Matt applies firefighting lessons to leading marketing teams
(18:10) - – Triaging “fire drills” and protecting your team’s focus
(20:00) - – How to prioritize ruthlessly (and what real prioritization means)
(22:30) - – From IC to VP: how your mindset and responsibilities shift
(24:45) - – Why leaders should double down on strengths—not fix weaknesses
(27:00) - – How self-assurance became Matt’s superpower as a leader
(30:00) - – The StrengthsFinder approach Matt uses with his team
(32:00) - – The value of executive coaching for marketing leaders
(33:30) - – The goal: build the best marketing team anyone’s worked on
(35:00) - – Why trust and 10x thinking unlock great marketing work
(37:30) - – Where product marketing sits inside Atlassian’s org
(39:00) - – How Atlassian uses Loom and async work to eliminate unnecessary meetings
(41:30) - – What qualifies as a real meeting at Atlassian
(43:00) - – Why async work helps global teams move faster
(46:00) - – How Atlassian balances async with intentional in-person gatherings
(48:00) - – Why trust changes how Slack and email are interpreted
(48:45) - – How Atlassian thinks about AI’s role in marketing
(51:00) - – Why it’s hard to stand out in an “AI-washed” market
(52:15) - – Matt’s mission: help make work suck less
(53:30) - – Final thoughts and wrap-up

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

B2B Ad Campaigns: Real Test Results from 7 Channels with Pranav Piyush Jun 26, 2025

Show notes

#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
(02:00) - – Why Paramark pulled real data from 7 B2B ad campaigns
(04:30) - – Attribution vs. experimentation: what most marketers get wrong
(08:00) - – Correlation vs. causation explained (with a LinkedIn example)
(10:45) - – How to run a real test (hint: you need a control)
(12:00) - – Branded search test results: $1M+ saved, no performance loss
(17:00) - – Why strong SEO makes or breaks branded search tests
(18:00) - – Billboard test: how one brand proved real lift with out-of-home
(21:30) - – What “digital out-of-home” looks like in B2B
(23:00) - – YouTube ad tests: one big win, one big flop
(26:00) - – How to run tests with small budgets ($500–$10K)
(30:30) - – Connected TV (CTV) test results from a Series F SaaS brand
(32:30) - – What happens when a multichannel test works—but isn’t efficient
(34:30) - – Paramark’s Exit Five sponsorship test (real numbers shared)
(38:00) - – Why content needs to drive short-term lift, not just long-term “brand”
(41:00) - – How Pranav used LinkedIn to drive inbound from day one
(43:00) - – Your attribution model is lying, give your audience more credit
(44:30) - – When 7 ad tests fail in a row…and the 8th one works
(46:00) - – Performance Max test: why it worked for one brand
(48:00) - – How long to run a test? Use data, not gut
(50:00) - – Bonus: Pranav’s hiring playbook for his first marketing leader
(54:00) - – Wrap up and 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

Why I Love Marketing (Quick Voice Note From Dave) Jun 24, 2025

Show notes

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.

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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