Create Messaging Reps Use (And Customers Remember) w/Madeleine Work | Chili Piper

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Episode 12: Madeleine Work, Senior Product Marketing Manager at Chili Piper (https://www.linkedin.com/in/madeleinework/) joins me (https://www.linkedin.com/in/joshua-chronister/) to break down how to create messaging that reps actually use and customers remember.

We talk about defining clear platform messaging, getting internal buy-in without watering it down, and why launches are never really one-and-done. We also dive into sales feedback loops, creative copy that still converts, and how Madeleine uses tools like Gong, Wynter, and Mutiny to test what’s working.

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💡 During our conversation, you’ll learn:

• How to A/B test website messaging

• How to create continuous feedback loops

• Getting internal buy-in on your messaging

• Balancing creativity and clarity in messaging

• Why product launches are on going and why you should repeat yourself

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🎙️ In our conversation, we cover: 

00:00 – Teaser: How Madeleine crowdsourced and tested messaging across her company

00:29 – Intro to Madeleine and what you’ll learn in the episode

01:44 – From content to product marketing: how the transition happened

03:24 – What she loved (and didn’t love) about content marketing

06:01 – The challenge of getting 100% messaging buy-in

06:55 – The collaborative H1 test: value, competitor, and persona buckets

08:53 – Running messaging through Wynter and Mutiny

12:21 – The importance of above-the-fold copy and first impressions

14:08 – UI images in messaging: show, don’t tell

15:10 – How Chili Piper defined its platform messaging

15:59 – “Demand conversion”: the phrase they landed on

17:47 – Messaging in a competitive landscape (and naming your competitors)

19:32 – How they brainstormed the phrase “demand conversion”

21:02 – Creativity vs. clarity: writing how you talk

23:44 – “No more complaints about unfair lead distribution”: voice-of-customer in action

25:18 – Marketing to marketers: easier and harder

26:13 – Why marketers don’t click UTM links—but give amazing form responses

28:46 – How Madeleine continuously refines messaging over time

29:53 – Sales feedback loops and scathing voice notes

30:23 – Refresh cadence: product pages, competitor pages, then restart

31:59 – PDF collateral vs. web content: keeping everything updated

33:35 – Launches Madeleine’s proud of (and what she learned)

35:12 – Why no one noticed the chat launch—and how they relaunched it

36:55 – The importance of repetition in product marketing

38:33 – Using Gong to track if messaging is landing with reps

40:04 – What living is all about: being a little uncomfortable

41:28 – Where to find Madeleine and her “Madeleine Love” folder

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🔦 Where to Find Emily:

LinkedIn: https://www.linkedin.com/in/madeleinework/

🔦 Where to Find Josh:

LinkedIn: https://www.linkedin.com/in/joshua-chronister/ 

Newsletter: https://onmessaging.substack.com/ 

Spotify: https://open.spotify.com/show/3E1gduFoKQYHiLNmNLzeF4?si=c3e2bc4bd362490f 

Apple Podcasts: https://podcasts.apple.com/gb/podcast/on-messaging/id1787098696 

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