The Exit Five Podcast

Latest Episodes:

Beyond Clicks: Building B2B Brands with Offline Ads with Amrita Gurney Oct 02, 2025

Show notes

#287 Brand Marketing | In this episode, Matt is joined by Amrita Gurney, a veteran B2B marketing leader who has scaled some of Canada’s fastest-growing startups and now works as a fractional CMO. At Float, she led bold offline campaigns, from billboards and buses to TV spots, that helped the company stand out against major banks and build lasting brand recall.

Matt and Amrita cover:

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

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

Timestamps

(00:00) - – Intro
(02:00) - – Amrita’s background and career journey
(03:20) - – Why Float invested in offline ads
(05:00) - – Launching their first billboard campaign
(07:00) - – Taking bold risks with creative
(09:00) - – Human-centered messaging vs. product copy
(11:00) - – Expanding into buses, subways, and airports
(14:00) - – Testing (or not testing) creative concepts
(15:00) - – What brand recall really means in B2B
(17:00) - – Measuring lift from offline campaigns
(20:00) - – Balancing brand vs. performance spend
(22:00) - – Lessons from consumer marketing in B2B
(24:00) - – How they chose cities and placements
(27:00) - – Budget breakdown and allocation
(31:00) - – Tracking TV ad performance
(33:00) - – How long to run campaigns for impact
(34:00) - – Advice for marketers considering offline ads
(36:00) - – Closing thoughts and takeaways

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter

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***

Brought to you by:

Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive.

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.

Optimizely - the AI platform for marketers. Build your own AI agents or pull from a directory of 50+ pre-built ones for marketing use cases. Their new Virtual Teammates can join meetings, complete tasks, support campaigns, and keep your website optimized. Learn more at optimizely.com/exitfive.

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 Be Great at Marketing Without Being a Subject Matter Expert with Kevin White, Head of Marketing at Common Room Sep 29, 2025

Show notes

#286 Growth | In this episode, Dave is joined by Kevin White, Head of Marketing at Common Room, a leading customer intelligence platform for go-to-market teams. Kevin shares insights from his experience helping teams capture and act on digital breadcrumbs to optimize their marketing and sales efforts.

Dave and Kevin cover:

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

Timestamps

(00:00) - - Intro to Kevin
(05:09) - - How to Be Good At Marketing When You're Not a Subject Matter Expert
(07:47) - - Why You Should Stay Close to Your Customer
(15:06) - - How to Manage a Marketing Team with Limited Resources
(17:25) - - Eliminating Ineffective Marketing Efforts to Drive Real Results
(22:23) - - Signups and Demos Boost From LinkedIn
(23:29) - - How to Attribute ROI in Multi-Platform Marketing
(27:39) - - Creating Authentic and Valuable Content
(32:18) - - Generating Pipeline with Economic Buyer Signals
(33:59) - - Increasing Digital Touchpoints
(37:57) - - How To Maximize Actionability, Volume, and Conversion Rate
(39:43) - - LinkedIn Measurement

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 Turn Your Company Story Into Actionable Marketing Ideas with Pranav Piyush Sep 25, 2025

Show notes

#285 Creative Strategy | In this episode, Dave is joined by Pranav Piyush, Founder & CEO of Paramark, a measurement platform helping B2B and B2C companies run smarter marketing experiments. Pranav is known for turning strategy documents into repeatable creative processes that generate campaigns, ads, and content tied directly to a company’s story.

Dave and Pranav cover:

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

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

Timestamps

(00:00) - – Intro and audience roll call
(04:00) - – Why narratives often get stuck in a Google Doc
(07:00) - – Foundational docs you need before creating campaigns
(12:00) - – Category entry points and jobs-to-be-done explained
(16:00) - – How to feed company inputs into AI tools
(22:00) - – Generating ad campaign ideas with real examples
(24:00) - – Using analogies (like basketball) to explain complex concepts
(27:00) - – Where AI falls short (and why human judgment matters)
(30:00) - – Mining sales call transcripts for campaign hooks
(34:00) - – Turning customer objections into marketing messages
(38:00) - – Repurposing podcasts, presentations, and blog posts into new formats
(42:00) - – Systemizing idea generation for repeatable output
(46:00) - – Closing thoughts and audience Q&A

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 Use Cognitive Behavioral Branding to Create New Categories with Ari Yablok, Head of Brand at Island Sep 22, 2025

Show notes

#284 Brand | Dave sits down with Ari Yablok, Head of Brand at Island, to share his approach to creating a brand in the cybersecurity space. Ari shares his journey from agency life to leading the brand narrative at Island, where he helped build the concept of the "enterprise browser."

Dave and Ari Cover:

The key differences between category creation and strategic positioning, and why it matters for B2B marketers
The steps to building a brand story that resonates with both your internal team and your target audience
How focusing on the last 20% of branding efforts can elevate your company above the competition

Timestamps

(00:00) - - Intro to Ari
(03:24) - - Rapidly Growing Enterprise Browser Company Secures $375M in Series D Funding
(07:33) - - SEO Strategy vs Branding
(13:00) - - How Brand is an Art and a Science
(18:15) - - Challenges in Cybersecurity Branding
(19:59) - - Early Stage Marketing
(26:54) - - Cognitive Behavioral Branding
(32:03) - - How Ari Manages Projects with the Brand Team
(34:13) - - Comfortable vs. Uncomfortable Approaches to Brand Strategy
(38:31) - - What Founders Really Want to Do
(43:37) - - Balancing the Day-to-Day with Visionary Goals

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

From Employee #4 to CMO: The Path to Marketing Leadership with Sylvia Lepoidevin, CMO at Kandji Sep 18, 2025

Show notes

#283 Marketing Leadership | In this episode, Dave is joined by Sylvia Lepoidevin, CMO of Kandji, a leading platform for managing and securing Apple devices in the workplace. Sylvia shares her journey from employee #4 to CMO at Kandji, driving the company’s growth to a $850M valuation. She talks about her experience building efficient marketing teams, leveraging AI, and creating impactful brand experiences.

Dave and Sylvia cover:

How AI is reshaping marketing roles and enabling smaller, more efficient teams
Strategies for internal marketing that align and energize cross-functional teams
Product launches and creative campaigns for brand-driven growth

Timestamps

(00:00) - - Intro to Sylvia
(03:48) - - From Marketing Hire to CMO
(08:33) - - Understanding Equity and Financial Outcomes
(11:15) - - Wealth and Career Growth
(13:55) - - Why It’s Important to Have a Clear Career Narrative
(18:47) - - Mastering Storytelling in Team Meetings
(22:05) - - How to Engage Your Team
(22:41) - - Leveraging Feedback Loops to Build a Successful Team
(28:12) - - AI Is Enabling Smaller, More Efficient Teams
(31:55) - - AI’s Impact on Marketing
(34:55) - - How Kandji Is Expanding Their Team
(37:46) - - Achieving 10x Growth Through Product-Led Strategies
(41:26) - - Leveraging Competitor and Apple-Specific Keywords
(44:50) - - Minimizing Hiring Risk: Test Roles First

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

Research-First CRO: How Data Leads to Better Marketing Decisions with Haley Carpenter Sep 15, 2025

Show notes

#282 CRO | Matt is joined by Haley Carpenter, founder of Chirpy, a conversion rate optimization agency. Haley has nearly a decade of CRO experience across agency, SaaS, and eCommerce, and she’s known for helping brands use research and testing to make smarter marketing decisions.

Matt and Haley cover:

Why CRO isn’t just A/B testing, and how research should guide every optimization effort
How to approach CRO when you don’t have massive website traffic, including scrappy testing methods and tools
The role of messaging, value props, and social proof in driving higher conversions (and where B2B often lags behind DTC)

By the end, you’ll have a clearer picture of how to approach CRO as a system, not just a set of tests.

Timestamps

(00:00) - – Intro
(01:00) - – Who is Haley Carpenter
(02:00) - – What CRO really means
(05:00) - – Research vs. testing explained
(09:00) - – Where to start CRO on a website
(12:00) - – Testing with limited traffic
(16:00) - – Using data for smarter decisions
(19:00) - – Building a culture of testing
(23:00) - – How to report CRO results
(28:00) - – Scrappy tools: Clarity & Hotjar
(32:00) - – What B2B can learn from DTC
(36:00) - – Why messaging matters more than features
(40:00) - – The power of social proof
(46:00) - – Common blockers to CRO success
(48:00) - – A surprising test result (+7% sales)
(50:00) - – Vanity metrics vs. real business outcomes
(54:00) - – 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

The Future of GTM and Sustainable Growth with Chris Walker, CEO at Passetto Sep 11, 2025

Show notes

#281 Growth | In this episode, Dave is joined by Chris Walker, CEO of Passetto, and a prominent voice on LinkedIn, where he has been pushing the boundaries of B2B marketing for years. Chris shares actionable insights and tactics on social media strategy, what has changed in marketing over the last five years, and how to build effective feedback loops and flywheels.

Dave and Chris also cover:

The future of GTM and the evolving role of the CMO
Why sustainable growth is the only path forward
The transformative role AI will play in B2B marketing

Timestamps

(00:53) - - Intro to Chris Walker
(02:40) - - Managing different perspectives on social media
(07:12) - - The ROI of podcasts and social media engagement
(12:35) - - Why real-time feedback loops are valuable
(18:10) - - Shifting from "growth at all costs" to sustainable growth
(24:00) - - Rethinking marketing measurement and ROI
(30:10) - - Splitting marketing teams: strategy vs. pipeline creation
(37:15) - - How AI is reshaping B2B marketing teams
(45:20) - - Chris’s approach to creativity and focus
(50:05) - - Predictions for the future of B2B marketing
(51:43) - - Outro

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 Cookie Cutter Marketing Doesn’t Work with Gurdeep Dhillon, CMO at ContentStack Sep 08, 2025

Show notes

#280 Strategy | In this episode, Dave is joined by Gurdeep Dhillon, CMO of Contentstack. Gurdeep has built an impressive career leading marketing at some of the biggest names in enterprise software, from SAP to Adobe, Marketo to Zoura. Now at Content Stack, he's challenging conventional B2B marketing wisdom in rethinking how enterprise companies should approach demand generation and brand building. In this conversation, Dave and Gurdeep dive deep into why marketing is ultimately a game of memory and reputation, not just lead generation.

Dave and Gurdeep cover:

The role of Demand Gen in 2025 (and what's changed)
Why Brand and Reputation should be prioritized over Lead Generation
Proven strategies to create urgency and close sales deals in enterprise markets
A glimpse into ContentStack’s team structure and how they plan for growth

Timestamps

(00:00) - - Intro to Gurdeep
(05:42) - - Brand and Audience Marketing
(06:54) - - How the Role of Demand Gen is Changing
(11:04) - - Brand and Reputation > Lead Generation
(15:54) - - How Contentstack is Doing Demand Gen
(18:32) - - How to Create Urgency to Win Sales Deals
(20:13) - - Making a Good Offer in B2B Marketing
(21:29) - - Why Being Bold and Taking Risks is Important in Marketing
(26:03) - - Selling Your Vision to Leadership
(28:44) - - How Contentstack Has Over 10,000 Global ICP Accounts
(33:27) - - Team Structure at Contentstack
(38:25) - - Running Marketing and Operating a High-Performing Team
(40:41) - - Setting Effective Annual Plans
(42:56) - - AI’s Role in Marketing
(46:30) - - 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

The Unfiltered Truth About Video Marketing and AI with Holly Xiao and Dave Gerhardt Sep 04, 2025

Show notes

#279 Content Strategy | In this episode, Dave joins Holly Xiao from HeyGen for an unfiltered conversation about where AI and video marketing are headed. Holly leads B2B marketing at HeyGen, an AI-powered video platform, and she sat down with Dave to dig into what’s working (and what’s not) when it comes to creating content that actually connects.

This recording is from a discussion Dave and Holly did with the AI Marketing Alliance --> https://www.aimarketingalliance.com/

Dave and Holly cover:

Why video hits differently in B2B and how to make yours stand out without blowing your budget
How AI is reshaping the content production cycle and freeing up marketers to focus on storytelling
Why early adoption matters, and how small teams can use AI to punch above their weight

You can expect a candid, practical conversation about how to scale content, stay relevant, and make the most of AI.

Timestamps

(00:00) - – Intro
(00:18) - – Why this conversation matters
(01:35) - – AI is making marketing exciting again
(02:44) - – Dave’s early bet on video
(04:44) - – How LinkedIn video exploded
(06:01) - – ROI vs. brand building
(07:16) - – From connection to conversion
(09:01) - – Why video feels more human
(11:07) - – “Maybe your videos suck”
(13:13) - – The problem with corporate videos
(15:01) - – The value of repetition and reps
(17:25) - – How AI speeds up content cycles
(19:42) - – Real AI tools Dave is using
(21:19) - – Decks, data, and automation
(23:44) - – Why creativity still wins
(26:06) - – The return of the creative CMO
(28:20) - – Personalized content at scale
(30:19) - – AI vs. in-person experiences
(33:01) - – Do audiences care if it’s AI?
(35:47) - – What makes an AI video work
(38:24) - – Using AI to test and scale video
(41:05) - – What small teams should do first
(44:43) - – Final advice: be an early adopter

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 B2B Marketers Are Actually Using AI for Content Sep 01, 2025

Show notes

#278 Content | In this episode, Dave brings together five B2B marketers who aren’t just talking about AI, they’re actually using it to change how their teams work. Each finalist from the Exit Five x Walnut AI Sessions takes the (virtual) stage to demo their workflow, share results, and answer questions from the judges.

Here’s what you’ll hear:

Jillian Hoefer’s “content concierge” GPT trained on proprietary research to surface stats, quotes, and data for blogs, sales decks, and thought leadership
Jake Heap’s workflow using Meshy + VEO 3 to turn a simple mascot into animated 3D brand characters in minutes
Jessica Lytle’s no-code ROI calculator built in Lovable that sales reps now run live on calls to build business cases
Ugi Djuric’s high-volume content engine that scrapes industry news and sales call transcripts, then uses AI to summarize, generate content ideas, and even score leads
Anton Ruis’ AI-powered buyer brief builder that pulls real-time economic data and tailors sales messaging to specific personas

It’s part workshop, part competition, and packed with creative, tactical ways to put AI to work in B2B marketing today.

Timestamps

(00:00) - – Dave kicks off in a tux
(01:35) - – Record-breaking registrations
(02:13) - – Meet the judges: Benny & Jess
(07:01) - – Jillian’s “victim of repurposing” intro
(07:41) - – Building a “content concierge” GPT from research data
(09:05) - – Injecting stats + quotes into blogs and decks
(13:01) - – How one report fueled 9+ months of content
(18:01) - – Jake on bringing AI into marketing ops
(19:24) - – Turning a mascot into a 3D character with Meshy
(20:09) - – Animating it in VEO 3 (no designer needed)
(23:24) - – Cutting animation time from weeks to minutes
(27:38) - – Jessica builds a no-code ROI calculator in Lovable
(30:47) - – AEs use it live on sales calls
(31:31) - – Adding benchmarks + transparency to ROI math
(38:49) - – Ugi’s AI engine scrapes + summarizes industry news
(41:06) - – Training custom GPTs on expert insights
(47:46) - – Anton’s real-time buyer briefs from economic data
(50:21) - – Tailoring briefs for CROs, enablement, PMMs
(54:05) - – Judges crown the winning use case + Dave’s 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

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