#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

#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.

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
• (01:27) - – Why this conversation matters
• (02:44) - – AI is making marketing exciting again
• (03:53) - – Dave’s early bet on video
• (05:53) - – How LinkedIn video exploded
• (07:10) - – ROI vs. brand building
• (08:25) - – From connection to conversion
• (10:10) - – Why video feels more human
• (12:16) - – “Maybe your videos suck”
• (14:22) - – The problem with corporate videos
• (16:10) - – The value of repetition and reps
• (18:34) - – How AI speeds up content cycles
• (20:51) - – Real AI tools Dave is using
• (22:28) - – Decks, data, and automation
• (24:53) - – Why creativity still wins
• (27:15) - – The return of the creative CMO
• (31:14) - – Personalized content at scale
• (33:13) - – AI vs. in-person experiences
• (35:55) - – Do audiences care if it’s AI?
• (38:41) - – What makes an AI video work
• (41:18) - – Using AI to test and scale video
• (43:59) - – What small teams should do first
• (47:37) - – Final advice: be an early adopter

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

#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
• (02:44) - – Record-breaking registrations
• (03:22) - – Meet the judges: Benny & Jess
• (08:10) - – Jillian’s “victim of repurposing” intro
• (08:50) - – Building a “content concierge” GPT from research data
• (10:14) - – Injecting stats + quotes into blogs and decks
• (14:10) - – How one report fueled 9+ months of content
• (19:10) - – Jake on bringing AI into marketing ops
• (20:33) - – Turning a mascot into a 3D character with Meshy
• (21:18) - – Animating it in VEO 3 (no designer needed)
• (24:33) - – Cutting animation time from weeks to minutes
• (30:32) - – Jessica builds a no-code ROI calculator in Lovable
• (33:41) - – AEs use it live on sales calls
• (34:25) - – Adding benchmarks + transparency to ROI math
• (41:43) - – Ugi’s AI engine scrapes + summarizes industry news
• (44:00) - – Training custom GPTs on expert insights
• (50:40) - – Anton’s real-time buyer briefs from economic data
• (53:15) - – Tailoring briefs for CROs, enablement, PMMs
• (56:59) - – Judges crown the winning use case + Dave’s wrap-up

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