The Exit Five Podcast

By Exit FiveBusiness Entrepreneurship Marketing

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Typical duration
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per episode

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The Exit Five Podcast episodes

June 26, 2025B2B Ad Campaigns: Real Test Results from 7 Channels with Pranav Piyush
#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:
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.
Visit hatch.fm to learn more
51 min
June 24, 2025Why I Love Marketing (Quick Voice Note From Dave)
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:
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.
Visit hatch.fm to learn more
3 min
June 23, 2025The Future of B2B Marketing: AI, Execution, and Craft with Kieran Flanagan
#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
(01:00) - – Kieran’s marketing journey
(03:00) - – His 2-year mission framework
(05:00) - – Advice for early-career marketers
(06:30) - – Why the grind still matters
(08:00) - – Ireland’s SaaS and startup scene
(09:00) - – Balancing operator vs. manager
(11:00) - – AI-generated “How to work with me”
(13:30) - – Kieran’s push-and-pull leadership style
(15:00) - – Giving direct creative feedback
(17:00) - – Why “collaborative brainstorms” fail
(18:00) - – The value of strong opinions
(19:00) - – Learning through tough feedback
(20:00) - – ChatGPT as a creative partner
(22:00) - – Claude vs. ChatGPT vs. Gemini
(24:00) - – Prompting differences in GPT-3.5 vs. 4.0
(26:00) - – Decision fatigue and AI loyalty
(27:00) - – Where AI is taking B2B marketing
(28:00) - – From answers to actions
(30:00) - – Micro-audiences and personalization
(32:00) - – The return of branded traffic
(33:00) - – Why AI reignited Kieran’s spark
(35:00) - – Avoiding AI-induced multitasking burnout
(36:30) - – Deep work vs. whack-a-mole
(37:30) - – Don Draper meets ChatGPT
(38:30) - – Picking a lane: tech vs. creative
(40:00) - – The value of podcasting practice
(41:00) - – Building a prompt muscle
(43:00) - – How Kieran trains GPTs
(45:00) - – Prompting tips for marketers
(46:00) - – The future CMO: part IC, part leader
(47:00) - – How agencies will evolve with AI
(48:00) - – In-person is back
(49:00) - – Overrated AI use cases
(50:00) - – Favorite tool: GenSpark
(52:00) - – Mistakes marketers make with AI
(53:00) - – Does anyone care if it’s AI?
(54:00) - – Lessons from fatherhood
(55:00) - – 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:
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.
Visit hatch.fm to learn more
53 min
June 19, 2025Email Deliverability: What Every B2B Marketer Needs to Know
#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
(02:10) - – Meet Sarah and Alex
(04:15) - – Why email deliverability matters more than subject lines
(06:30) - – How to tell if you have a deliverability problem
(08:45) - – The most useful (and overlooked) deliverability metrics
(11:05) - – Why replies matter more than opens or clicks
(13:30) - – Tools Alex and Sarah use to monitor deliverability
(15:45) - – Should you buy a dedicated IP?
(17:40) - – How to evaluate platforms for deliverability
(20:00) - – Getting sales to care about data hygiene
(22:30) - – Deliverability tips for small senders and solopreneurs
(25:15) - – Subdomains vs. secondary domains
(28:05) - – How many inboxes per domain is too many?
(30:10) - – Best practices for cold outreach
(33:00) - – How security bots skew your open and click data
(36:00) - – What counts as “spam” (and how filters decide)
(39:15) - – How to re-engage cold or inactive lists
(42:00) - – What to A/B test in subject lines (and when it’s pointless)
(45:10) - – How to build a healthy, opt-in list from scratch
(48:00) - – When to stop emailing cold leads
(50:15) - – Welcome sequence tips for engaged subscribers
(53:10) - – How to warm up a new domain
(56:30) - – Final takeaways and advice
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:
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.
Visit hatch.fm to learn more
53 min
June 16, 2025How to Structure and Lead a Full-Funnel B2B Marketing Org with Kelly Hopping
#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
(02:00) - – What Demandbase actually does
(04:00) - – How the Demandbase marketing team is structured
(06:30) - – Who owns what: brand, content, demand, SDRs
(09:00) - – Account-based marketing + broad demand gen
(11:30) - – What a CMO actually does at this stage
(14:00) - – Kelly’s early CMO learning curve
(17:00) - – Planning your first 90 days as a CMO
(19:00) - – Balancing pipeline today vs. positioning for tomorrow
(21:30) - – What changed between a bad Q4 and strong Q1
(25:00) - – How Kelly thinks about yearly pipeline pacing
(28:00) - – Staying relevant in a fast-moving MarTech world
(30:30) - – Why marketers need to work like product teams
(34:00) - – “I am the ICP”: Why product marketing works better
(35:30) - – Kelly’s #1 job as CMO: Make sales love marketing
(38:00) - – Becoming a peer to product and revenue leaders
(40:30) - – Best-performing channel right now: in-person events
(42:00) - – Brand, attribution, and pipeline are all connected
(43:30) - – How Kelly’s team is using AI today
(45:00) - – The future of marketing roles in an AI-powered world
(47:30) - – Why she’s still learning new AI tools herself
(50:00) - – Why AI is fun again for marketers
(51:00) - – 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:
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.
Visit hatch.fm to learn more
48 min
June 12, 2025How to Get Sales on Board with Your Marketing Content with Kira Federer, VP of SMB Marketing at Paramount Advertising
#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
(04:54) - - Kira’s Career Journey From Sales Enablement to Product Marketing
(08:08) - - Challenges of Building Community / Getting Connected with Exit Five
(14:24) - - How To Get Sales To Use Content from Marketing
(16:59) - - How to Align Marketing and Sales Teams
(23:05) - - Effective Messaging and Having a Core Company Narrative
(28:13) - - Why You Should Identify What Differentiates Your Business
(31:56) - - How To Create Strong Brand Positioning
(34:41) - - Why You Need To Have A Clear Vision And Strong Point of View in Marketing
(36:25) - - “The Risk Of Insult Is The Price Of Clarity”
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:
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.
Visit hatch.fm to learn more
40 min
June 09, 2025Mastering Lifecycle Marketing: Real-World Tactics from Leading B2B Teams
#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
(01:30) - – Meet Charlotte and Naomi
(03:15) - – How they define lifecycle marketing
(05:00) - – What they’ve changed their minds about recently
(08:10) - – Plain text vs. designed emails
(10:00) - – Their frameworks for experimentation
(12:30) - – How to test in low-volume environments
(14:50) - – Common mistakes in A/B testing
(16:00) - – What a day in lifecycle marketing looks like
(18:10) - – How they (actually) use AI in their workflows
(22:00) - – Building a reporting foundation for lifecycle
(25:00) - – Naomi’s example of measuring aha moments
(27:00) - – Quick definitions of lifecycle marketing
(28:30) - – Tips for writing lifecycle campaigns that actually matter
(29:00) - – Favorite lifecycle campaigns they’ve run
(31:00) - – Why revamping welcome flows is always worth it
(33:00) - - Frameworks they use for building new flows
(36:00) - – What to do *after* onboarding ends
(37:30) - – Using behavior-based triggers and milestones
(39:30) - – Surprise and delight moments in B2B
(41:00) - – Creating assets with a lean team
(44:00) - – Systems and templates that save time
(46:00) - – Navigating multi-year sales cycles with lifecycle content
(49:00) - – Why benchmarks are often misleading
(51:00) - – Final advice: audit often, talk to your team, and keep learning
(53:00) - – Wrap-up and where to find Naomi and Charlotte
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:
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.
Visit hatch.fm to learn more
50 min
June 05, 2025Category Creation Playbook: How to Be Irreplaceable in B2B Marketing (with Josh Lowman)
#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
(01:30) - – Josh’s backstory and founding Gold Front
(04:45) - – How Gold Front became a category design studio
(07:00) - – What “category creation” really means
(10:15) - – Why being irreplaceable is the real goal
(13:20) - – The four paths to category leadership
(17:05) - – Why Drift didn’t succeed in creating a true category
(21:00) - – Clay and Notion as category-of-one examples
(23:50) - – Marketing vs. actual customer perception
(27:15) - – Can Exit Five be more than the “Dave Gerhardt community”?
(30:10) - – How to scale brand DNA beyond the founder
(33:00) - – Defining Exit Five’s ethos as a company
(35:20) - – Strategy as a company-wide unifier
(38:10) - – Advice for CMOs on driving strategy with CEOs
(40:45) - – Why strategy is always the root cause
(42:15) - – Vibe marketing and the rise of right-brain thinking
(45:00) - – Josh’s mental health journey and long-term therapy
(48:30) - – LinkedIn, self-worth, and staying grounded
(51:00) - – Weightlifting, discipline, and mental clarity
(54:00) - – Daily habits that improve mindset
(57:15) - – What 30 days of silent meditation does to your brain
(01:02:00) - – Final thoughts on presence, self-work, and leadership
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:
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.
Visit hatch.fm to learn more
58 min
June 02, 2025B2B Website Optimization: Real Examples and Live Feedback
#251 Website Optimization | In this episode, Danielle is joined by Guy Yalif, Chief Evangelist at Webflow; Talia Wolf, Founder and CEO of Getuplift; and Scott Cappuzzo, Web Strategist at Webflow. Together, they dig into what actually makes a B2B website convert and why most homepages are missing the mark.
This panel brings deep experience in conversion rate optimization, UX strategy, and messaging clarity, sharing practical tips and live feedback from real B2B websites submitted by Exit Five members.

Danielle, Guy, Talia, and Scott cover:
The #1 mistake B2B marketers make on their homepage and how to fix it with customer-driven messaging
Smart ways to test and optimize (even if you don’t have high traffic)
How to write CTAs that meet buyers where they are in the journey (and get more clicks)

Whether you’re planning a homepage redesign or just want to tighten your headline and CTA copy, this session will help you make smarter website decisions grounded in expert feedback and real examples.

Timestamps
(00:00) - – Intro
(01:00) - – Meet the expert panel
(03:40) - – The biggest homepage mistake
(06:20) - – What customers *really* want
(07:00) - – The CTA copy test
(08:10) - – Why A/B testing isn’t always right
(10:50) - – Personalization you can actually use
(13:00) - – What’s a “good” conversion rate?
(16:20) - – CTA clarity vs. creativity
(20:00) - – Why messaging must come first
(22:00) - – How to do helpful personalization
(28:10) - – Emotional drivers in B2B
(30:10) - – Live teardown #1: ContactMonkey
(36:50) - – Visuals, CTAs, and clarity
(42:10) - – Live teardown #2: StreamTech
(47:30) - – Outdated visuals and lost messaging
(51:05) - – Chatbots: thoughtful vs. disruptive
(52:20) - – Live teardown #3: CallTrackingMetrics
(55:00) - – Final ratings + 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:
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.
Visit hatch.fm to learn more
59 min
May 29, 20256 Steps to Building a Customer Insights Program with Shoshana Kordova
#250 Customer Insights | Matt sits down with Shoshana Kordova, a 3x founding product marketer and former journalist who now helps B2B tech startups craft customer-infused messaging through her consultancy, Peel Product Marketing. Shoshana recently launched a customer insights playbook for the PMM Jetpack, equipping marketers with tools and templates to run more effective customer interviews.

Matt and Shoshana cover:
Why a customer insights program is more than “just talking to customers” and how to turn interviews into a repeatable system that drives messaging, positioning, and case studies
How to collaborate across teams (especially with CS and product) to get buy-in and avoid stepping on toes
The most common mistakes B2B marketers make with interviews and how to get the kind of insights you can actually use
Whether you're a product marketer, content strategist, or leading a GTM team, this episode is packed with actionable takeaways to build messaging that resonates.
Timestamps
(00:00) - – Intro
(01:05) - – Meet Shoshana: From Journalism to Product Marketing
(02:15) - – What Is “Customer-Infused Messaging”?
(04:00) - – Why Customer Insights Beat Surface-Level Deliverables
(06:00) - – How to Work with CS and Sales Without Stepping on Toes
(09:00) - – Navigating Competing Priorities Across Teams
(11:20) - – Selling the Value of Customer Interviews Internally
(15:20) - – The 6 Steps to Building a Customer Insights Program
(17:15) - – Step 1: Aligning Goals with Stakeholders
(18:55) - – Step 2: Building a Customer Interview Pipeline
(21:00) - – Step 3: Keeping Stakeholders in the Loop (Hint: Use Slack)
(25:15) - – Step 4: How to Run a Great Customer Interview
(30:45) - – Focus on Problems, Not Just the Product
(33:20) - – Uncovering Real ROI with Better Follow-Ups
(34:30) - – Step 5: Documenting What Actually Matters
(36:50) - – How to Organize Insights into a Shared Database
(39:40) - – Step 6: Putting Insights to Work (Case Studies, Messaging, ICPs)
(42:00) - – Should You Hire an External Interviewer?
(44:15) - – What’s a Realistic Interview Cadence?
(45:45) - – Other Places to Find Customer Insights (When Interviews Aren’t Possible)
(47:20) - – Final Tips: Mining G2 Reviews, Webinars, and Internal Teams
(48:34) - – Wrap-Up and Where to Find Shoshana
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:
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.
Visit hatch.fm to learn more
51 min

About The Exit Five Podcast

From the publisher's feed

The #1 resource for B2B marketing professionals. Each week, hosts Dave Gerhardt and Dasha Shakov sit down with B2B marketers to break down everything from strategy and leadership to the channels and tactics that drive growth, plus what it takes to build a career in marketing. You'll find real ideas you can put to work right away, and the gut check and inspiration to keep getting better at your job.