Maddermore

Matt Schenker spent 10 years as a licensed therapist, meditation teacher, and management trainer before discovering a critical gap in sales management. Through years of coaching sales managers, he noticed a persistent problem: most managers weren't trained in effective management practices, even though manager-rep relationship health is the single strongest predictor of sales rep stress and performance—more important than customer responsiveness or deal velocity. This wasn't a knowledge gap; it was a visibility and execution problem.

Starting about a year before this interview, Matt partnered with a co-founder with deep enterprise sales and mobile app development experience. Rather than build first and search for customers, they conducted rigorous research: four consecutive 6-week sprints where they interviewed roughly 100 sales teams each, accumulating insights on pain points and best practices. Using these findings, they built low-code, no-code proof of concepts to test with real users—one being an AI-powered post-call report that integrates transcripts from tools like Gong and Order.

The product uses Claude as its LLM to analyze sales calls against behavior science rubrics developed with academic advisors. Managers receive feedback on what drove or hindered effectiveness and adaptability in their interactions—insights no director or employee typically provides. The founding CTO, recently hired from a medical AI company, has committed to delivering an internal MVP within two weeks.

Maddermore's first beta customers came through referral from Matt and his co-founder's deep networks in sales and training. Rather than launching publicly, they deliberately chose to deepen relationships with these early users through pilots, offering custom feedback reports based on their interview learnings. The approach prioritized trust and impact over immediate scale.

The interview-first, build-second approach validated genuine demand—they found that sales managers are starved for specific, contextualized feedback on their team's engagement and their own effectiveness. The behavioral science foundation (informed by academic advisors who took equity) proved credible with customers. What's less clear is how quickly they can convert pilots to paying customers and whether the AI-powered insights will sustain differentiation in an increasingly crowded sales enablement market.

As of the interview, Maddermore is pre-revenue in beta with several customers running pilots. Matt is financing ongoing work through coaching, consulting, and training engagements in the sales space—a tradeoff that slows product development but keeps the lights on. The company targets a 6-9 month runway to a more polished MVP and publicly accessible product, with plans to start charging beta customers within weeks of the CTO's internal launch.