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
• (07:17) - - Brand and Audience Marketing
• (08:29) - - How the Role of Demand Gen is Changing
• (12:39) - - Brand and Reputation > Lead Generation
• (17:29) - - How Contentstack is Doing Demand Gen
• (20:07) - - How to Create Urgency to Win Sales Deals
• (21:48) - - Making a Good Offer in B2B Marketing
• (23:04) - - Why Being Bold and Taking Risks is Important in Marketing
• (29:29) - - Selling Your Vision to Leadership
• (32:10) - - How Contentstack Has Over 10,000 Global ICP Accounts
• (36:53) - - Team Structure at Contentstack
• (41:51) - - Running Marketing and Operating a High-Performing Team
• (44:07) - - Setting Effective Annual Plans
• (46:22) - - AI’s Role in Marketing
• (49:56) - - Closing Thoughts

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 our friends at Revenue Hero. It’s 2024, your buyer has probably moved on to an alternative after a few minutes of not hearing from you, let alone 29 hours.

What those companies need is automated scheduling for qualified leads.

And that’s where RevenueHero comes in. Their platform is the fastest way for qualified leads to schedule a meeting with your sales team. Plus they have the most sophisticated matching algorithm so all your leads get booked with the right rep whether they are a new account or already a customer. Check them out at revenuehero.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

In this episode, we’re delivering another B2B marketing lesson in under 10 minutes—no fluff, just practical insights.

Matthew Carnevale, Marketing Manager at Exit Five, shares a game-changing mental model for marketers: the GM vs. Player mindset. Inspired by a sports analogy, Matthew explains why thinking like a General Manager—hiring resources and creating leverage—will help you tackle big opportunities without waiting for bandwidth.

Learn how shifting your mindset from “doing the work” to “making the plays happen” can unlock faster results, level up your career, and drive impact for your business.

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 our friends at Revenue Hero. It’s 2024, your buyer has probably moved on to an alternative after a few minutes of not hearing from you, let alone 29 hours.

What those companies need is automated scheduling for qualified leads.

And that’s where RevenueHero comes in. Their platform is the fastest way for qualified leads to schedule a meeting with your sales team. Plus they have the most sophisticated matching algorithm so all your leads get booked with the right rep whether they are a new account or already a customer. Check them out at revenuehero.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

This episode is from Drive 2024, our first-ever in-person event for B2B marketers in Burlington, Vermont. Peter Mahoney, Chief Commercial Officer at GoTo, and author of The Next CMO, shared strategies for building and leading high-performing marketing organizations.

Peter covers:

• 10 Guidelines for building (or re-building) a marketing organization
• Running marketing: how to build your CMO operating system
• 5 strategies for effectively leading an organization

Timestamps

• (00:00) - - Intro to Peter
• (05:08) - - Are there requirements for being a CMO?
• (10:06) - - Do you really want to be a CMO?
• (10:35) - - How CMOs spend their time
• (11:18) - - 10 Guidelines for building (or re-building) a marketing organization
• (13:05) - - 1. Align to your marketing strategy
• (14:05) - - 2. Ensure the financial model supports your organization
• (16:00) - - 3. Make it simple
• (16:35) - - 4. Build in clear accountability
• (17:51) - - 5. Resist layers
• (19:31) - - 6. Do not design around the individual
• (22:15) - - 7. Clearly define what is a service center and what is an outcome center
• (22:53) - - 8. Build the smallest organization necessary
• (24:04) - - 9. Make a hiring decision as difficult as laying someone off
• (25:04) - - 10. Define your full-time vs. part-time vs. outsource strategy
• (27:52) - - Running marketing: Building your CMO Operating System
• (29:15) - - 5 strategies for leading marketing
• (32:02) - - Q&A
• (39:28) - - Closing Remarks

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 our friends at Revenue Hero. It’s 2024, your buyer has probably moved on to an alternative after a few minutes of not hearing from you, let alone 29 hours.

What those companies need is automated scheduling for qualified leads.

And that’s where RevenueHero comes in. Their platform is the fastest way for qualified leads to schedule a meeting with your sales team. Plus they have the most sophisticated matching algorithm so all your leads get booked with the right rep whether they are a new account or already a customer. Check them out at revenuehero.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

When done right, paid spend is like throwing gasoline on the flames of what’s working in your marketing. Done wrong – it’s just a huge waste of time and money.

In this episode, Dave Gerhardt hosts an live session with John Short, CEO of Compound Growth Marketing (CGM), and Kym Parker, SVP of Media Strategy at CGM, who walk through tried and true strategies they’ve built from managing over $50 million in paid spend.

They also cover:

• How to choose which strategy is best for you and exactly how to target the right ICP
• The three keys to successful paid media, like setting up actionable reporting
• How to identify how much you can spend for leads/account at each stage of the sales and marketing funnel

Timestamps

• (00:00) - - Intro to John and Kym
• (07:29) - - Choosing the Perfect Paid Media Strategy
• (11:57) - - The $100 CPL Myth
• (15:32) - - Three Keys to Successful Paid Media
• (18:10) - - Qualification Is Critical in ABM Success
• (19:48) - - How You Should Think About Bidding Algorithms
• (22:32) - - Prospect Experience: The Campaign Funnel
• (24:12) - - Using a Multi-Channel Approach
• (29:32) - - Mid-Intent Funnel Examples
• (33:04) - - Executing on a Paid Acquisition Strategy
• (39:13) - - Tailoring Your Messaging for Buying Committee Engagement
• (43:47) - - Balancing Funnel Strategies
• (46:28) - - Justifying Higher Costs
• (50:43) - - Channel Testing and Target Comparison
• (52:08) - - How to Master Paid Media in Enterprise Marketing

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 our friends at Revenue Hero. It’s 2024, your buyer has probably moved on to an alternative after a few minutes of not hearing from you, let alone 29 hours.

What those companies need is automated scheduling for qualified leads.

And that’s where RevenueHero comes in. Their platform is the fastest way for qualified leads to schedule a meeting with your sales team. Plus they have the most sophisticated matching algorithm so all your leads get booked with the right rep whether they are a new account or already a customer. Check them out at revenuehero.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

In this episode, we’re delivering another B2B marketing lesson in under 10 minutes.

Matthew Carnevale, Marketing Manager at Exit Five, breaks down the story behind the best ad he’s ever created—one that generated $77,822 in MRR over two years. Spoiler: it wasn’t fancy production or clever wordplay. The secret? Raw, undeniable social proof.

Matthew shares why raw social proof, like screenshots, before-and-after results, and authentic testimonials, outperforms polished case studies or logos. By the end, you’ll know how to gather and use social proof effectively to make your marketing efforts stand out and drive real results.

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 our friends at Revenue Hero. It’s 2024, your buyer has probably moved on to an alternative after a few minutes of not hearing from you, let alone 29 hours.

What those companies need is automated scheduling for qualified leads.

And that’s where RevenueHero comes in. Their platform is the fastest way for qualified leads to schedule a meeting with your sales team. Plus they have the most sophisticated matching algorithm so all your leads get booked with the right rep whether they are a new account or already a customer. Check them out at revenuehero.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

This episode is from Drive 2024, Exit Five's first-ever in-person event for B2B marketers in Burlington, Vermont. Ross Simmonds, Founder of CEO at Foundation & Distribution.ai , hosted a session on creating and distributing B2B content that drives real results.

Ross covers:

• Why "create once, distribute forever" should be your mantra for content marketing.
• How to blend educational, engaging, entertaining, and empowering content to captivate your audience.
• Tactical approaches to dominate distribution channels like LinkedIn, Reddit, and niche communities.

Timestamps

• (00:00) - - Intro to Ross
• (02:55) - - Content Creation Mistakes
• (05:49) - - Thinking Like a Modern Media Company: Distribution Strategy
• (09:22) - - Crafting and Distributing Engaging, Impactful Content
• (14:19) - - How to Continuously Engage Your audience
• (17:10) - - Optimizing Strategy through Reddit and Niche Communities
• (24:07) - - Tactical Content Distribution Tips
• (29:54) - - Embracing AI and Automation
• (33:38) - - Framework: Research, Create, Distribute, Optimize
• (35:15) - - Creative Strategies for Engaging Your Online Audience
• (36:43) - - Write Casually: Communicate Like a Friend
• (41:30) - - The Power of Reusing Stories in Content Creation

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 our friends at Revenue Hero. It’s 2024, your buyer has probably moved on to an alternative after a few minutes of not hearing from you, let alone 29 hours.

What those companies need is automated scheduling for qualified leads.

And that’s where RevenueHero comes in. Their platform is the fastest way for qualified leads to schedule a meeting with your sales team. Plus they have the most sophisticated matching algorithm so all your leads get booked with the right rep whether they are a new account or already a customer. Check them out at revenuehero.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

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
• (05:23) - - From 1st Marketing Hire to CMO
• (10:08) - - Understanding Equity and Financial Outcomes
• (12:50) - - Wealth and Career Growth
• (15:30) - - Why It’s Important to Have a Clear Career Narrative
• (20:22) - - Mastering Storytelling in Team Meetings
• (25:31) - - How to Engage Your Team
• (26:07) - - Leveraging Feedback Loops to Build a Successful Team
• (31:38) - - AI Is Enabling Smaller, More Efficient Teams
• (35:21) - - AI’s Impact on Marketing
• (38:21) - - How Kandji Is Expanding Their Team
• (41:12) - - Achieving 10x Growth Through Product-Led Strategies
• (44:52) - - Leveraging Competitor and Apple-Specific Keywords
• (48:16) - - Minimizing Hiring Risk: Test Roles First

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 our friends at Revenue Hero. It’s 2024, your buyer has probably moved on to an alternative after a few minutes of not hearing from you, let alone 29 hours.

What those companies need is automated scheduling for qualified leads.

And that’s where RevenueHero comes in. Their platform is the fastest way for qualified leads to schedule a meeting with your sales team. Plus they have the most sophisticated matching algorithm so all your leads get booked with the right rep whether they are a new account or already a customer. Check them out at revenuehero.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

In this episode, we’re delivering another B2B marketing lesson in under 10 minutes.

Matthew Carnevale, Marketing Manager at Exit Five, introduces the "Billboard Test," a mental model to evaluate whether your marketing copy can grab attention in an instant. Inspired by how billboards must captivate drivers at full speed, this test helps you refine your ads, social posts, and emails for today’s audience.

Matthew shares three key elements of the Billboard Test—concise messaging, eye-catching visuals, and memorability through creativity—and explains how to apply them to make your marketing impossible to ignore. By the end, you’ll know how to capture attention and hold it, even in the busiest of feeds.

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 our friends at Revenue Hero. It’s 2024, your buyer has probably moved on to an alternative after a few minutes of not hearing from you, let alone 29 hours.

What those companies need is automated scheduling for qualified leads.

And that’s where RevenueHero comes in. Their platform is the fastest way for qualified leads to schedule a meeting with your sales team. Plus they have the most sophisticated matching algorithm so all your leads get booked with the right rep whether they are a new account or already a customer. Check them out at revenuehero.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

This is a re-run of one of our top episodes, where Dave is joined by Kyle Coleman, CMO at Copy.ai. Kyle went from Individual Contributor to Senior Director at Looker and Director to CMO at Clari. During his time there, he helped both companies 10x their revenue.

In this episode, they chat about

• The importance of leadership team alignment and why the CRO & CFO should be your best friend
• How marketing can impact pipeline and the standard it should be held to
• Why you should build a marketing calendar around the product roadmap

Timestamps

• (00:00) - - Kyle's exposure to B2B marketing and strategy
• (06:51) - - Gaining expertise in marketing metrics and standards
• (11:29) - - Balancing Efficiency and Creativity in Sales Outreach
• (15:08) - - Importance of an Internal Partnership with the Sales Team
• (17:48) - - Aligning marketing goals with revenue generation
• (19:31) - - Co-creating Qualified Opportunities with ICP
• (24:36) - - Importance of Sales and Marketing Collaboration
• (30:18) - - How CROs and CMOs can balance long-term vision and short-term outcomes
• (35:28) - - The lightning strike strategy
• (36:21) - - "Marketing Moments:" Calendaring significant events to drive business goals and team performance
• (39:37) - - Using Shield analytics to identify and repost popular content
• (47:13) - - How to simplify complex questions to extract key insights
• (50:40) - - Building a networking resource for professional growth
• (53:43) - - Closing thoughts

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 our friends at Revenue Hero. It’s 2024, your buyer has probably moved on to an alternative after a few minutes of not hearing from you, let alone 29 hours.

What those companies need is automated scheduling for qualified leads.

And that’s where RevenueHero comes in. Their platform is the fastest way for qualified leads to schedule a meeting with your sales team. Plus they have the most sophisticated matching algorithm so all your leads get booked with the right rep whether they are a new account or already a customer. Check them out at revenuehero.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

In today's challenging business landscape, marketers face the daunting task of not only crafting an efficient marketing plan, but implementing it quickly, proving its value, and continuously adapting the plan on the fly. The ever-changing macroeconomic environment adds an extra layer of complexity, making success even harder to achieve.

In this episode, Rowan Tonkin, CMO at Planful, and Dave Gerhardt, Founder of Exit Five, lead you through the essential steps to building your plan, getting it approved, and unlocking the full potential of your marketing efforts.

They cover:

• Tips to build a powerful marketing plan that aligns with your business objectives.
• Strategies to gain plan approval from executives and board members
• Best practices and practical approaches to flawlessly execute your marketing plan, turning ideas into measurable results.
• Insights into the advantages of scenario planning and how it can prepare your marketing team to adapt to the ever-changing economic landscape.

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 our friends at Revenue Hero. It’s 2024, your buyer has probably moved on to an alternative after a few minutes of not hearing from you, let alone 29 hours.

What those companies need is automated scheduling for qualified leads.

And that’s where RevenueHero comes in. Their platform is the fastest way for qualified leads to schedule a meeting with your sales team. Plus they have the most sophisticated matching algorithm so all your leads get booked with the right rep whether they are a new account or already a customer. Check them out at revenuehero.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

This episode is from Drive 2024, our first-ever in-person event for B2B marketers in Burlington, Vermont. Devin Reed, Founder of The Reeder and expert in content strategy, shared a session on building a strong personal and company presence on LinkedIn.

Devin covers:

• Identifying your “one word” to own and dominate a category on LinkedIn.
• Why your content strategy should focus on personal LinkedIn profiles for max reach and engagement.
• A step-by-step framework for producing and distributing CEO or executive-led LinkedIn content.

Timestamps

• (00:00) - - Intro to Devin
• (06:11) - - How to Build Trust at Scale
• (12:04) - - 10 Undeniable Reasons B2B Leaders Should Get Active on LinkedIn Right Now
• (14:16) - - Pick Your “One Word” to Guide Your Content Category
• (19:30) - - How to Narrow Your Audience
• (26:28) - - How to Pick Content Pillars & Topics
• (30:55) - - Outlining Your Production Process
• (32:49) - - How to Measure & Iterate LinkedIn Success
• (37:48) - - Using Company Pages vs Personal Pages
• (38:29) - - Communicating with Your CEO
• (39:41) - - How to Get Your Whole Team Involved in LinkedIn
• (40:22) - - Niching Down with Your “One Word”
• (41:51) - - Prioritizing Engagement on LinkedIn
• (43:02) - - Applying This Framework to Other Channels
• (43:18) - - Revising Your Voice and Tone
• (45:13) - - How to Pick Your “One Word” (Revisited)
• (47:18) - - Reach Versus Teach

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 our friends at Revenue Hero. It’s 2024, your buyer has probably moved on to an alternative after a few minutes of not hearing from you, let alone 29 hours.

What those companies need is automated scheduling for qualified leads.

And that’s where RevenueHero comes in. Their platform is the fastest way for qualified leads to schedule a meeting with your sales team. Plus they have the most sophisticated matching algorithm so all your leads get booked with the right rep whether they are a new account or already a customer. Check them out at revenuehero.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