#281 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
• (02:09) - – Who is Haley Carpenter
• (03:09) - – What CRO really means
• (06:09) - – Research vs. testing explained
• (10:09) - – Where to start CRO on a website
• (13:09) - – Testing with limited traffic
• (17:09) - – Using data for smarter decisions
• (20:09) - – Building a culture of testing
• (24:09) - – How to report CRO results
• (29:09) - – Scrappy tools: Clarity & Hotjar
• (34:54) - – What B2B can learn from DTC
• (38:54) - – Why messaging matters more than features
• (42:54) - – The power of social proof
• (48:54) - – Common blockers to CRO success
• (50:54) - – A surprising test result (+7% sales)
• (52:54) - – Vanity metrics vs. real business outcomes
• (56:54) - – Closing thoughts

Send guest pitches and ideas to hi@exitfive.com
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
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***

This episode of the Exit Five podcast is brought to you by Qualified.

AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine.

That’s where Qualifed comes in with Piper, their AI SDR agent.

Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound?

Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline.

The Agentic Marketing era has arrived. And if you’re a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help.

Hire Piper, the #1 AI SDR Agent, and grow your pipeline today.

You can learn more at qualified.com/exit5

#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
• (03:49) - - Managing different perspectives on social media
• (08:21) - - The ROI of podcasts and social media engagement
• (13:44) - - Why real-time feedback loops are valuable
• (19:19) - - Shifting from "growth at all costs" to sustainable growth
• (25:09) - - Rethinking marketing measurement and ROI
• (33:04) - - Splitting marketing teams: strategy vs. pipeline creation
• (40:09) - - How AI is reshaping B2B marketing teams
• (48:14) - - Chris’s approach to creativity and focus
• (52:59) - - Predictions for the future of B2B marketing
• (54:37) - - Outro

Send guest pitches and ideas to hi@exitfive.com
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

***

This episode of the Exit Five podcast is brought to you by Qualified.

AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine.

That’s where Qualifed comes in with Piper, their AI SDR agent.

Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound?

Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline.

The Agentic Marketing era has arrived. And if you’re a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help.

Hire Piper, the #1 AI SDR Agent, and grow your pipeline today.

You can learn more at qualified.com/exit5

#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
• (06:51) - - Brand and Audience Marketing
• (08:03) - - How the Role of Demand Gen is Changing
• (12:13) - - Brand and Reputation > Lead Generation
• (17:03) - - How Contentstack is Doing Demand Gen
• (19:41) - - How to Create Urgency to Win Sales Deals
• (21:22) - - Making a Good Offer in B2B Marketing
• (22:38) - - Why Being Bold and Taking Risks is Important in Marketing
• (28:57) - - Selling Your Vision to Leadership
• (31:38) - - How Contentstack Has Over 10,000 Global ICP Accounts
• (36:21) - - Team Structure at Contentstack
• (41:19) - - Running Marketing and Operating a High-Performing Team
• (43:35) - - Setting Effective Annual Plans
• (45:50) - - AI’s Role in Marketing
• (49:24) - - Closing Thoughts

Send guest pitches and ideas to hi@exitfive.com
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

***

This episode of the Exit Five podcast is brought to you by Qualified.

AI is the hottest topic in marketing right now. And one thing we hear a lot of you marketers talking about is how you can use AI Agents to help run your marketing machine.

That’s where Qualifed comes in with Piper, their AI SDR agent.

Piper is the #1 AI SDR Agent on the market according to G2, and hundreds of companies like Box, Asana, and Brex, have hired Piper to autonomously grow inbound pipeline. How good does that sound?

Qualified customers are seeing a massive business impact with Piper: a 3X increase in meetings booked and a 2X increase in pipeline.

The Agentic Marketing era has arrived. And if you’re a B2B marketing leader looking to scale pipeline generation, Piper the #1 AI SDR Agent is here to help.

Hire Piper, the #1 AI SDR Agent, and grow your pipeline today.

You can learn more at qualified.com/exit5