Platform repositioning is messy. You’re changing how the market understands you, how customers experience value, and how internal teams talk about the product. In this episode, I sit down with Jameelah Calhoun, VP of Market Strategy at Forter, to unpack what it really takes to reposition a platform when the pressure is high and the stakes are real.

Jameelah shares what repositioning looked like at Eventbrite during COVID, when the events industry changed overnight. Eventbrite needed to expand beyond “ticketing tool” and be understood as a broader suite of marketing resources for event organisers. She breaks down how to start with the data you already have, spot where product market fit is soft, and find the moments in the journey where customers hit friction.

From there, we get into the practical decisions that drive outcomes. Jameelah explains why segmentation is non-negotiable, how to identify the highest leverage problem, and what it looks like to reduce friction through changes to sign-up, packaging, and the path to value. She also talks about building internal trust through tight collaboration with product and engineering, plus using lightweight experiments and an experimentation roadmap to keep decisions focused and defensible.

We close with a messaging critique of Calendly. Their homepage nails clarity by repeating “scheduling” relentlessly, but that same simplicity can undersell the more advanced value for sophisticated buyers, like integrations, payments, and workflow automation. We talk about the opportunity to keep the core promise while elevating the positioning so it reflects what the product has become.

Key Takeaways

Start with existing research and performance data before you build a new story

• Segment your audience properly, because different users need different value cues
• Find the highest leverage problem, then focus your work there
• Build trust through close partnership with product and engineering
• Use lightweight experiments and a clear roadmap to validate decisions
• Messaging should stay clear, but still reflect the full value of the product

LINKS

Messaging Critique: Calendly 

Connect with Jameelah: 

LinkedIn: https://www.linkedin.com/in/jameelah-calhoun/ 

Podcast:  https://www.unpopulardecisions.com/ 

Connect with Elle:

LinkedIn: https://www.linkedin.com/in/elle3izabeth/