Always Be Testing

In this episode of Always Be Testing, host Tye DeGrange sits down with Kevin Weatherman, co-founder of Upscale AI, a performance streaming platform using AI to power connected TV ads for DTC brands. With a rich background that includes being the first business hire at multiple startups, angel investing, and co-founding a global run club, Kevin shares his journey from selling limo rides to Google employees to scaling AI-driven advertising solutions. Their conversation covers Kevin’s approach to identifying market trends, the evolution of A/B testing, connected TV measurement strategies, AI in creative production, the intersection of brand and performance marketing, influencer and affiliate strategies, hiring in the AI era, and personal insights from his journey to sobriety.

What is Always Be Testing?

Always Be Testing explores the experiments, insights, and growth stories shaping the future of affiliate and partner marketing in B2B SaaS. Hosted by industry veterans, the show dives deep into real-world lessons from the people driving measurable impact at companies like Google, HubSpot, Ramp, Webflow, G2, and beyond.

Each episode uncovers what happens when today's most innovative marketers challenge assumptions, run smarter experiments, and build programs that scale revenue through meaningful partnerships. If you’re in affiliate, partnerships, or SaaS growth — this is your front-row seat to how the best do it (and what they’ve learned along the way