Co-Founder & CEO - AI Retail Planning Autopilot
Lead AI-native inventory-planning intelligence venture as Co-Founder & CEO, developing autopilot planning intelligence for SMB operators with AI, connecting across channels and ERPs, and externalizing institutional memory.
The Opportunity
FutureSight is seeking a Co-Founder & CEO to lead Maestro, an AI-native inventory-planning intelligence venture currently in development at our studio. This is a co-founder partnership with meaningful founder equity, not a salaried executive role.
Maestro is an autopilot planning intelligence for SMB operators managing physical inventory complexity without a planning team. It connects across channels and ERPs, handles routine decisions silently, and surfaces exceptions with context and a recommended action before they become revenue losses. The institutional memory that today lives only in a planner's head gets externalized, structured, and queried in plain language.
We didn't just build a thesis; we validated it directly with the market. We have spoken with founders, VP E-Commerce leaders, merchandise planners, and multi-channel operators at DTC and specialty retail brands across the US. The market signal is clear:
Market Context
We are targeting a large, structurally underserved segment: SMB operators managing multi-channel physical inventory complexity at $5M–50M revenue — importers, distributors, Amazon aggregators, and specialty retailers. The beachhead SAM is estimated at $200M–$225M across approximately 15K–16K brands in the US and Canada. Excel is the universal incumbent! 5/5 buyers in our discovery sprint were on spreadsheets, with zero dedicated planning tools in use. EBITDA across the $10–50M DTC cohort is compressed to 7.25% in 2025 with revenue declining ~4.6% YoY. Planning waste attacks the margin stack directly.
About FutureSight
FutureSight is a leading venture studio that co-creates world-class software companies with values-driven entrepreneurs from
Posted June 7, 2026