#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

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

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

#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

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

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

#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

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

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

#277 Growth | Dave is joined by Emma Robinson, Head of B2B Marketing at Canva, and Kristine Segrist, VP of Consumer Marketing at Canva. Together, Emma and Kristine lead the teams driving Canva’s growth across both enterprise and consumer audiences, helping the company scale into a platform now used by over 95% of the Fortune 500.

Dave, Emma, and Kristine cover:

• How Canva balances brand-building with pipeline accountability, and why they view brand investment as long-term growth.
• The playbook Canva uses to turn bottom-up adoption into enterprise deals, including how product signals guide upsell and expansion.
• How their team structure, data science investments, and creative bets (like the Love Your Work campaign) work together to scale B2B marketing without losing Canva’s approachable brand identity.

This episode offers a practical look at how one of the world’s most recognizable platforms approaches B2B growth.

Timestamps

• (00:00) - – Intro

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

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

#276 Career Growth | Dave is joined by Kady Srinivasan, CMO at You.com, an AI-first company building infrastructure for enterprise agents. Kady has led marketing at some of the world’s most recognizable companies, including Dropbox, Klaviyo, and Lightspeed, where she scaled teams, drove massive revenue growth, and navigated ICP pivots. Now, she’s bringing that experience into the fast-changing world of AI.

Dave and Kady cover:

• How to evolve as a CMO across industries, personas, and business models
• The three core systems CMOs need to scale teams and drive alignment
• How AI is reshaping marketing roles, workflows, and the skills future CMOs will need

You’ll walk away with lessons you can apply to your own career, no matter what market or role you’re in.

Timestamps

• (00:00) - – Intro

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

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

#275 LinkedIn Strategy | In this episode, Dave is joined by Brad Zomick, a B2B marketing consultant and host who has helped founders and executives build their presence on LinkedIn. Together they break down why a strong LinkedIn strategy is no longer optional for founders, it’s one of the most effective growth levers in B2B today.

Dave and Brad cover:

• Why LinkedIn is still the best channel for founders to build authority, attract talent, and connect with customers
• How to turn everyday founder communications into high-impact LinkedIn content
• The unexpected ROI of founder-led content, from recruiting and partnerships to real-time message testing

If you’ve been wondering how to turn LinkedIn into a real growth engine for your brand, this episode is your blueprint.

Timestamps

• (00:00) - – Intro

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

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

#274 Growth | In this episode, Dave is joined by Sean Lane, Founding Partner at BeaconGTM and RevOps expert, to talk about scaling RevOps in B2B. With over a decade of experience at Drift and other B2B SaaS companies, Sean shares actionable tips for marketers looking to align operations with business goals.

Dave and Sean cover:

• How to build alignment between sales, marketing, and ops
• Why early-stage companies must align operational complexity with their growth maturity
• How continuous planning helps marketing and ops teams stay agile as business challenges come up

Timestamps

• (00:00) - - Intro to Sean

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

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

#273 Leadership | Matt is joined by Rachel Weeks, a veteran B2B marketing leader with over 20 years of experience guiding companies through acquisitions, layoffs, and tech disruption. Rachel has led both corporate and field marketing teams and is passionate about recognition-driven team cultures that retain and empower top talent.

Matt and Rachel cover:

• How to build a recognition strategy that actually improves retention (without needing a big budget or fancy platform)
• Why employee motivation dips during times of stress, layoffs, or AI disruption and what great leaders do differently
• The role of marketing in internal culture: from branding the program to building peer-driven engagement

Whether you’re managing a small team or leading an entire department, this episode is packed with practical insights to help you build a culture where marketers feel valued, motivated, and ready to stay.

Timestamps

• (00:00) - – Intro

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

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

#272 Presentation Skills | Matt is joined by Vincent Pierri, a speaking coach who helps executives and marketers craft compelling, high-stakes talks. With a background as a pastor and public communicator, Vincent has developed a repeatable framework that helps B2B marketers improve how they show up in front of a room, whether it’s a conference keynote, a boardroom pitch, or a weekly team update.

Matt and Vincent cover:

• The 4-part framework behind talks that stick: Tension, Trust, Teaching, Takeaway
• How to pick the right topic for your talk (and avoid cramming in too much)
• Why authenticity and simplicity matter more than slide design, and how to keep your delivery grounded and effective

Whether you’re prepping for Inbound, Exit Five’s Drive, or just your next big internal presentation, this episode will help you nail the structure and mindset behind a talk that resonates.

Timestamps

• (00:00) - - Intro

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

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

#271 GTM Engineering | In this episode, Dave is joined by John Short, CEO of Compound Growth Marketing, along with Cammy Keiler, Justin Johnson, and Dan Guenet. Together, they break down the rise of GTM engineering, what it is, how it differs from RevOps, and why B2B teams are investing in it.

Dave and the crew cover:

• The core difference between RevOps and GTM engineering (and why the latter is more focused on building than just integrating)
• Real GTM engineering use cases, from AI-powered sales tools to mid-funnel campaigns that go way beyond ebooks
• How GTM engineers are driving higher revenue per employee and why this role should be one of your first five marketing hires

Whether you’re hiring or just GTM-curious, you’ll leave this episode with a clear definition of the role, real-world examples, and tactical ways GTM engineers drive impact.

Timestamps

• (00:00) - – Intro

Send guest pitches and ideas to [email protected]
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership

***

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