Co-Founder & CEO - AI Retail Planning Autopilot

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:

• Autopilot is the vision: Every named competitor generates recommendations that humans still have to act on manually. No product at this revenue tier is building toward full autonomous execution of the planning lifecycle. Maestro's product vision is full autopilot: the system owns the buy decision, allocation, and markdown trigger end-to-end. But buyers earn that trust incrementally, starting with routine decisions handled silently and exceptions surfaced with context.
• The pain is in the dollars, not the dashboards: Documented annual losses across just five buyer accounts total $1.25–1.5M+. Buyers currently spend $0–500/month on software; the entire planning budget is tied up in headcount. The payback case is immediate, and ROI demonstration, not feature demos, will be the critical sales motion.
• Institutional memory failure is systemic and unresolved: One SVP with 30 years of domain expertise described relying entirely on personal recall to flag which materials, colours, and styles underperformed last season. When he leaves, that knowledge disappears, and no tool captures it today. Every buyer interviewed described a version of this problem.

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