#312 | In this episode, Udi Ledergor joins Dave to break down the ideas behind his new book, Courageous Marketing, and why most B2B marketing fails because it plays it safe. He also shares his journey from marketer #1 to CMO to Chief Evangelist at Gong, where he led category creation, brand, and marketing through massive scale. They unpack how Gong built a brand that actually stood out, what it means to punch above your weight as a B2B marketer, and how to think about brand ROI without fake dashboards.

Timestamps

• (00:00) - – Meet Udi and his path into marketing
• (08:16) - – Early career lessons and building marketing from zero
• (15:16) - – How Gong found product-market fit and nailed positioning early
• (19:26) - – Courageous Marketing: why Udi wrote it and what it really means
• (23:16) - – Brand first: personality, positioning, then visuals
• (28:20) - – Campaigns that punched above their weight (billboards, experiments, perception hacks)
• (35:10) - – Proving brand impact: soft ROI, pipeline, and exec buy-in
• (47:40) - – The future: product-led marketing, AI, and courageous teams

Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Today's episode is brought to you by Knak.

Email (in my humble opinion) is the still the greatest marketing channel of all-time.

It’s the only way you can truly “own” your audience.

But when it comes to building the emails - if you’ve ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever.

That’s why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.

• Frustrated by clunky email builders? You need Knak.
• Tired of ‘hoping’ the email you sent looks good across all devices? Just test in Knak first.
• Big team making it hard to collaborate and get approvals? Definitely Knak.

And the best part? Everything takes a fraction of the time.

See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.

***

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

#312 | Jess Lytle (Head of Marketing at Exit Five) hosts a roundtable with a group of email experts on what’s actually working in email, SMS, and in-app messaging right now. They dig into AI’s impact on the inbox, how to sound human when everyone’s using the same tools, and why relevance beats volume. The group also breaks down how to personalize without being creepy, what to do with “lurkers” who never click but still convert, and how to build messaging that survives the AI slop era. It’s a sharp look at how B2B marketers can cut through the noise, earn attention, and actually get people to respond.

Timestamps

• (00:17) - — Jess welcomes everyone
• (02:30) - — Why email and messaging aren’t dead… bad messaging is
• (05:58) - — How AI changed the inbox and why standing out is harder than ever
• (06:34) - — Why human senders beat brand senders in email
• (10:03) - — Writing emails like you were invited into someone’s personal space
• (12:18) - — Balancing stakeholder requests vs. what your audience actually wants
• (15:28) - — Real talk on AI personalization, enrichment, and where it actually works
• (21:33) - — Subject lines, preview text, and how people really decide what to open
• (23:08) - — Email stories and empathy-driven content that outperform
• (29:03) - — SMS, in-app, and email orchestration: what to use when
• (36:20) - — Measuring impact when email is assist, not hero
• (44:20) - — The future: AI-driven workflows, data challenges, and what’s coming
• (53:00) - — Favorite tools (Claude, NotebookLM, etc.) and how people use them

Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Today's episode is brought to you by Knak.

Email (in my humble opinion) is the still the greatest marketing channel of all-time.

It’s the only way you can truly “own” your audience.

But when it comes to building the emails - if you’ve ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever.

That’s why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.

• Frustrated by clunky email builders? You need Knak.
• Tired of ‘hoping’ the email you sent looks good across all devices? Just test in Knak first.
• Big team making it hard to collaborate and get approvals? Definitely Knak.

And the best part? Everything takes a fraction of the time.

See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.

***

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

#311: Dave goes solo this week (his decision, he said give me the mic; but Dan is also on him about podcast downloads around the holidays) with a quick November breakdown from real life - recapping the Exit Five team trip to Arizona, a big leadership update at the company, and covering five timeless marketing principles that matter more than ever (if you care about fighting AI slop). He also talks about recovering from hip surgery (everyone’s been asking how old he is), what he’s been reading, and a Thanksgiving food debate.

Timestamps

• (00:00) - - Intro + the sunglasses bit
• (04:08) - - Getting back into podcasting + November setup
• (05:38) - - The 5 timeless marketing principles
• (14:28) - - How to apply those principles in real marketing
• (15:38) - - Exit Five team trip to Arizona
• (17:28) - - Why in-person time matters
• (21:20) - - Dave’s hip surgery and recovery
• (23:50) - - What he read and watched in November
• (27:20) - - The Thanksgiving overrated/underrated debate
• (29:40) - - Big news: Dan promoted to CEO and what’s next for Exit Five

Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Today's episode is brought to you by Knak.

Email (in my humble opinion) is the still the greatest marketing channel of all-time.

It’s the only way you can truly “own” your audience.

But when it comes to building the emails - if you’ve ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever.

That’s why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.

• Frustrated by clunky email builders? You need Knak.
• Tired of ‘hoping’ the email you sent looks good across all devices? Just test in Knak first.
• Big team making it hard to collaborate and get approvals? Definitely Knak.

And the best part? Everything takes a fraction of the time.

See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.

***

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