Rebranding starts with listening (AI can help), with Michael Yehoshua
Table of contents
Rebrands don’t fail because of bad design. They fail because marketers stop listening. Learn how WiseStamp CMO Michael Yehoshua turned customer conversations into the foundation of an enterprise rebrand, showing how AI in rebranding works best when it’s used to listen, not just create.
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Episode summary
In this episode of Radically Transparent, host Jennifer Gutman sits down with Michael Yehoshua, CMO of WiseStamp, for one of the most honest conversations the show has had about branding, AI, and the uncomfortable truth most marketing leaders don’t want to hear:
Your customers already have the answers; you’re just not listening closely enough.
Michael brings over 20 years of experience building and scaling B2B marketing engines, including multiple successful exits in cybersecurity. What makes this conversation hit differently, however, is how radically simple his lesson is.
When Michael joined WiseStamp, the company was at a pivotal moment. It was financially strong. Yet despite advanced security, compliance, and scale, WiseStamp was still perceived as an SMB tool, creating hesitation among enterprise buyers.
To fix this, leadership did what many companies do: they hired a top-tier branding agency and invested heavily in a rebrand. What they received were beautiful concepts, refined typography, and polished logos. All focused on how the brand looked, not what customers actually needed to hear.
That’s when the alarm bells went off for Michael.
With just a small budget left, Michael made a bold decision: stop designing and start listening.
Instead of brainstorming taglines and visuals, he hit the road and picked up the phone. He met customers face-to-face across cities, sat with churned users, spoke with frustrated customers, and listened closely to satisfied ones. He mapped the entire buying journey, from problem recognition to renewal, and reviewed hundreds of recorded sales and support conversations.
This is where AI in rebranding became a force multiplier, not as a writing tool, but as a listening engine.
Rather than generating more content, Michael used AI to analyze massive volumes of real customer conversations. Clear patterns emerged: what customers cared about most, the language that resonated, where trust was built, and what ultimately triggered buying decisions.
Only after that analysis did Michael lead a rebrand, grounded entirely in customer truth.
The result? A masterclass in how AI in rebranding can produce messaging so clear and resonant that competitors began copying it. A positioning shift that the market instantly recognized. And a brand that reflects the enterprise value WiseStamp delivers.
Hot topics from the episode
- Why rebrands fail when customers aren’t part of the process
- How AI in rebranding unlocks real power for marketers through listening, not just content creation
- Why CMOs must be relentlessly customer-obsessed
- Why competitor copycats are often a sign you got it right
One rule every marketing leader should follow
Michael leaves marketers with a single, non-negotiable rule:
There is no greater gold mine in marketing than listening to your customers.
Visit them. Sit with them. Watch them use your product. Listen to their frustrations, in their words, not yours.
As Michael explains, using AI in rebranding makes this easy, but only if you stop using it to talk and start using it to listen. So if you’re rebranding, or even thinking about it, don’t move another pixel until you hear this conversation.
Meet Michael
Michael Yehoshua is the Chief Marketing Officer at WiseStamp, where he leads brand and go-to-market strategy, helping enterprise companies turn everyday emails into a strategic, branded touchpoint that’s measurable and memorable.
With over 20 years of experience building and scaling B2B marketing engines, he has led two successful exits in the cybersecurity space, most recently to Honeywell.
Michael is also a frequent speaker on content-driven growth and modern B2B storytelling, with a practical approach that pairs deep customer listening with AI workflows to spot patterns faster while keeping humans in charge of strategy and judgment.
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