The Exit Five Podcast

Latest Episodes:

#207: Strategy | Jason Lemkin on What Makes a Great VP Marketing in SaaS, Working with the CEO, and Lessons from SaaStr Jan 02, 2025

Show notes

Dave is joined by Jason Lemkin. Jason is the founder of SaaStr, the world’s largest community of SaaS executives, founders, and entrepreneurs. Before SaaStr, Jason founded EchoSign, which was sold to Adobe in 2011.

They discuss:

Why Jason started SaaStr
What makes a great VP of Marketing in SaaS and how to hire one
How tech and SaaS have changed since 2020
CROs vs CMOs
Importance of alignment between the CEO and marketing team

Timestamps

(00:00) - - Intro
(05:35) - - Understanding the Importance of Revenue Goals
(08:59) - - Evolving Motivations and Changing Perspectives
(13:05) - - From Solopreneur to Founder: The Journey of Exit Five
(17:01) - - The Challenge of Transitioning from Solopreneurship
(19:00) - - Insights into Jason's Content Creation Process
(21:44) - - Efficiency in writing: a five-minute rule
(26:52) - - LinkedIn: A Haven for Text-Based Writers
(28:18) - - LinkedIn's Good Community and Marketing Potential
(32:54) - - Importance of Building Relationships in Business
(37:39) - - Marketing Essentials: Brand, Field, Demand, Growth
(40:16) - - Finding the Right Fit: Aligning Marketing Roles with Company Vision
(43:21) - - Finding Alignment: The Role of Marketing in Company Leadership
(47:33) - - CROs and Marketing
(50:22) - - Balancing Heads: Sales, Marketing, and Post-Sales in SaaS Leadership
(53:42) - - Event Planning
(55:37) - - SaaStr: Connecting Founders and Revenue Professionals

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.

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#206: Drive | How to Build an AI-Powered $0 CAC Strategy with Kyle Coleman, CMO at Copy.ai Dec 30, 2024

Show notes

This episode is from Drive 2024, our first-ever in-person event for B2B marketers in Burlington, Vermont. Kyle Coleman, CMO at Copy AI and former SVP of Marketing at Clari, hosted a session on leveraging AI to create a $0 CAC strategy that drives demand generation. With a career spanning leadership roles in B2B SaaS, Kyle brings a wealth of experience in building high-performing teams and transforming go-to-market strategies.

Kyle covers:

Why developing a provocative point of view is critical to differentiate your brand
How to build a content flywheel that aligns operations, drives consistency, and improves velocity.
Strategies to reduce “go-to-market bloat” and streamline processes for sustainable growth.

Timestamps

(00:00) - - Intro to Kyle
(04:12) - - Content is strategy, but most companies have bad content
(05:23) - - Force a choice, not a comparison
(08:25) - - Book recommendations for thinking about your company differently
(11:20) - - Identifying core problems and target audience
(14:39) - - What is GTM Bloat?
(18:43) - - Beat the friction out of your process
(20:47) - - How to create a demand flywheel
(25:29) - - Non-negotiable content types
(26:52) - - Real thoughts from real subject matter experts
(31:36) - - Harness the power of the internet
(33:29) - - Always-on ways to capture the demand you create
(36:47) - - Q&A

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:

***

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

#205: Career | Do you really want to be CMO? Returning from Parental Leave, What's working in B2B marketing today with Amanda Natividad, VP of Marketing at SparkToro Dec 26, 2024

Show notes

Amanda Natividad is VP of Marketing at SparkToro. She's also a contributor for Adweek, a Le Cordon Bleu-trained chef, and a former journalist. Dave and Amanda catch up after Amanda's return to work after having her second child, talk about trends they are seeing in B2B marketing today and what Amanda's seen work at SparkToro (including email strategy and LinkedIn). Plus they talk about the path to CMO - and why Amanda enjoys being a team of one.

Timestamps

(00:00) - - Webinar Promotion Without Links and Returning to Work After Maternity Leave.
(06:04) - - The Emotional Impact of Parental Leave.
(08:40) - - Navigating Career Paths in Marketing.
(12:10) - - SparkToro's Audience Research Tool and Growth Strategy.
(14:31) - - VP of Marketing at SparkToro: Managing Top-of-Funnel, Organics, and Events.
(19:11) - - Rethinking the pursuit of status in business.
(22:10) - - Contemplating financial gains and their true value.
(23:10) - - Prioritizing time over extra income for happiness.
(29:26) - -Transitioning from Consulting to Content Business: The Evolution of Exit Five.
(32:01) - - The challenges and potential rewards of solopreneurship.
(34:16) - - Navigating Hiring and Trust in a Small Team
(38:05) - - Strategic Email Marketing at Sparktoro: Balancing Frequency and Impact.
(41:06) - - Sparktoro's Email Strategy: Quality over Quantity and List Management Tactics.
(43:08) - - The challenge of balancing marketing strategies.
(48:25) - - Optimizing LinkedIn Strategy: Pinning Comments and Zero-Click Content.
(50:32) - - Embedding Webinar Links in Blog Posts for Engagement
(52:53) - - 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:

***

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

#204: Inside the Exit Five Holiday Party | What’s Working in B2B Marketing and a Look Ahead to 2025 with the Exit Five Team Dec 23, 2024

Show notes

In this episode, Dave and the Exit Five team celebrate the end of the year with a holiday party for the Exit Five community. They share insights, lessons, and highlights from their growth and events in 2024, play a game show with Ding Zheng, sales rapper and co-founder of EventShark, and provide a sneak preview of what's in store for 2025.

Dave and the team cover:

2024 stats: How treating community as a product drove nearly 80% growth this year
The hottest content topics in B2B marketing in 2024
What's ahead for the Exit Five community in 2025

Timestamps

(00:00) - - Intro to the Exit Five Team
(09:57) - - Exit Five’s Year in Review
(11:55) - - Community Growth Stats
(15:49) - - Exit Five Content Strategy
(17:53) - - Community Awards
(23:14) - - Gameshow with Ding Zheng
(40:59) - - What’s in store for 2025
(48:11) - - Closing remarks

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:

***

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

#203: Strategy | Why Cookie Cutter Marketing Doesn’t Work with Gurdeep Dhillon, CMO at ContentStack Dec 19, 2024

Show notes

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
(05:42) - - Brand and Audience Marketing
(06:54) - - How the Role of Demand Gen is Changing
(11:04) - - Brand and Reputation > Lead Generation
(15:54) - - How Contentstack is Doing Demand Gen
(18:32) - - How to Create Urgency to Win Sales Deals
(20:13) - - Making a Good Offer in B2B Marketing
(21:29) - - Why Being Bold and Taking Risks is Important in Marketing
(26:03) - - Selling Your Vision to Leadership
(28:44) - - How Contentstack Has Over 10,000 Global ICP Accounts
(33:27) - - Team Structure at Contentstack
(38:25) - - Running Marketing and Operating a High-Performing Team
(40:41) - - Setting Effective Annual Plans
(42:56) - - AI’s Role in Marketing
(46:30) - - 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:

***

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

Be the GM, Not the Player: A Story on Creating Leverage in Marketing (Micro-Lesson) Dec 18, 2024

Show notes

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.

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:

***

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

#202: Marketing Leadership | How To Build A High Performing B2B Marketing Org with Peter Mahoney, CCO at GoTo Dec 16, 2024

Show notes

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
(03:33) - - Are there requirements for being a CMO?
(08:31) - - Do you really want to be a CMO?
(09:00) - - How CMOs spend their time
(09:43) - - 10 Guidelines for building (or re-building) a marketing organization
(11:30) - - 1. Align to your marketing strategy
(12:30) - - 2. Ensure the financial model supports your organization
(14:25) - - 3. Make it simple
(15:00) - - 4. Build in clear accountability
(16:16) - - 5. Resist layers
(17:56) - - 6. Do not design around the individual
(18:49) - - 7. Clearly define what is a service center and what is an outcome center
(19:27) - - 8. Build the smallest organization necessary
(20:38) - - 9. Make a hiring decision as difficult as laying someone off
(21:38) - - 10. Define your full-time vs. part-time vs. outsource strategy
(24:26) - - Running marketing: Building your CMO Operating System
(25:49) - - 5 strategies for leading marketing
(28:36) - - Q&A
(36:02) - - Closing Remarks

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:

***

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

#201: Paid Spend | Mastering B2B Paid Spend: A 2025 Roadmap for Marketers with John Short, CEO of Compound Growth Marketing and Kym Parker, SVP of Media Strategy Dec 12, 2024

Show notes

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
(05:54) - - Choosing the Perfect Paid Media Strategy
(10:22) - - The $100 CPL Myth
(13:57) - - Three Keys to Successful Paid Media
(16:35) - - Qualification Is Critical in ABM Success
(18:13) - - How You Should Think About Bidding Algorithms
(20:57) - - Prospect Experience: The Campaign Funnel
(22:37) - - Using a Multi-Channel Approach
(26:06) - - Mid-Intent Funnel Examples
(29:38) - - Executing on a Paid Acquisition Strategy
(35:47) - - Tailoring Your Messaging for Buying Committee Engagement
(40:21) - - Balancing Funnel Strategies
(43:02) - - Justifying Higher Costs
(47:17) - - Channel Testing and Target Comparison
(48:42) - - How to Master Paid Media in Enterprise 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:

***

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

The Secret Behind My Best Ad Ever: Raw Social Proof (Micro-Lesson) Dec 11, 2024

Show notes

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.

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:

***

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

#200: Drive | Create Once, Distribute Forever: Content Marketing & Distribution with Ross Simmonds, Founder and CEO at Foundation & Distribution.ai Dec 09, 2024

Show notes

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
(01:20) - - Content Creation Mistakes
(04:14) - - Thinking Like a Modern Media Company: Distribution Strategy
(07:47) - - Crafting and Distributing Engaging, Impactful Content
(12:44) - - How to Continuously Engage Your audience
(15:35) - - Optimizing Strategy through Reddit and Niche Communities
(20:41) - - Tactical Content Distribution Tips
(26:28) - - Embracing AI and Automation
(30:12) - - Framework: Research, Create, Distribute, Optimize
(31:49) - - Creative Strategies for Engaging Your Online Audience
(33:17) - - Write Casually: Communicate Like a Friend
(38:04) - - The Power of Reusing Stories in Content Creation

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:

***

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

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