#226: Messaging | In this episode, Dave sits down with Diane Wiredu, messaging expert and founder of Lion Words, a consultancy that helps B2B tech and SaaS companies achieve message-market fit so they can stand out, market more effectively, and sell more. Diane breaks down why most B2B messaging falls flat, how to fix it, and why messaging is more than just copy—it’s the bridge between positioning and execution.
Dave and Diane cover:
- The difference between positioning and messaging (and why both matter)
- How to create a messaging strategy that actually resonates
- Why most B2B messaging sucks and how to fix it
- How to structure homepage messaging for maximum impact
- How to get the most value from customer research for copywriting
Timestamps
- (00:00) - – Intro to Diane
- (03:49) - – What is message-market fit and why does it matter?
- (07:03) - – The biggest messaging mistakes B2B companies make
- (09:29) - – The difference between positioning and messaging (and why both matter)
- (12:57) - – How to create a messaging strategy that actually resonates
- (16:14) - – Signs your messaging isn’t working and how to fix it
- (19:48) - – The role of customer research in B2B messaging
- (23:21) - – How to structure a homepage message hierarchy that converts
- (29:09) - – What makes a great value proposition vs. a generic one
- (31:43) - – How to test and validate your messaging with real customers
- (35:27) - – Why messaging needs to be clear, not clever
- (38:58) - – Common struggles B2B teams face when implementing new messaging
- (42:34) - – Final takeaways
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
***
Today’s episode is brought to you by Walnut.
Why are we spending all this time on marketing… just to push buyers to a “Request a Demo” button? Even if they’re interested, no one wants to click that. No one wants to “talk to sales.” They just want to try the product for themselves!
Good news: now they can - with Walnut.
Walnut is the interactive demo platform for marketers who are done hiding their product and want to put it front and center.
You can build guided, self-serve demos in minutes. No engineers. No developers. No waiting. Embed them on your site. Drop them in emails. Let buyers explore your product on their terms - at any stage of the funnel.
And the best part? You get the data. See what features prospects are engaging with, where they drop off, and what’s actually driving pipeline.
500+ companies use Walnut - including Adobe and NetApp. Their teams save 400+ hours a year building demos… and have prevented over 1.5 million minutes of bad ones.
So if you want to drive more leads, shorten sales cycles, and actually show your product, go check out Walnut.io (and tell their team you heard about it on the Exit Five podcast!).
The Exit Five CMO Podcast (Hosted by Dave Gerhardt) 
