SPOTLIGHT: Skipping the SMB Trap and Building for Big Brands | Matt Allison, CEO & Founder @ Handraise

Matt Allison, CEO and Founder of Handraise, joins us to share why he's skipping the SMB trap and building an AI-powered media intelligence platform for enterprise from day one. Drawing on hard-won lessons from scaling TrendKite, Matt breaks down how Handraise is targeting $30K+ deals with brands like Walgreens and Hershey, the importance of patience in early go-to-market, and how AI is helping them build a more thoughtful, scalable, and enterprise-ready product from the start.

Matt also talks about:

- Why Handraise is skipping the SMB trap and going enterprise from day one

- What TrendKite taught him about building for high-value, high-retention customers

- Why patience and discipline matter when you're building an enterprise GTM motion

- How AI is helping Handraise build a more sophisticated product with a lean team

- Why being AI-first changes what's possible in product development

- How to build a sustainable business without chasing hypergrowth at all costs

Chapters:

00:00 Introduction to Matt Allison and Handraise

01:15 Why Handraise Is Going Enterprise From Day One

08:46 The Challenge: Building for $30K+ Enterprise Deals